From Martinique to Grenada, the Windward Islands trace the border of the southern Caribbean Sea. They include four countries, dozens of islands—many of them uninhabited—steady trade winds, and hundreds of miles of navigable coastline. This tropical playground is an ideal sailing destination for seasoned sailors and first-time charterers alike. 

At the northern end of the Windwards is Martinique, the only French territory of the group. With its fine wine, boulangeries and chic Paris fashions, it’s the island where resisting indulgence is ­hardest. It’s also a major yachting destination with skilled technicians, though it’s often the most expensive. Colorful colonial architecture dots the coastline, and cafes and restaurants line the beaches. 

St. Lucia’s mountainous coastline beckons to the south of Martinique, with tourist destinations such as the Pitons bringing well-deserved fame. Diving and snorkeling can provide equally spectacular views underwater. There is no shortage of all-inclusive luxury resorts and romantic retreats, especially in the area around the Pitons.

St. Vincent and the Grenadines, by contrast, is where sailors get away from the crowds. The west coast of the St. Vincent mainland is ­rural, secluded and steep, making anchoring and mooring a challenge. Almost no yacht services are available, ­except at the Blue Lagoon Hotel and Marina at the southern end of the island. 

From there, sailors can leave the mainland behind and head south to the Grenadines for idyllic turquoise Caribbean water. Sandy, uninhabited islets speckle the horizon. The Tobago Cays are on par with the Pitons as far as cinematic vistas, and are the destination for charter yachts.

Grenada, the southernmost island in the Windwards (just outside the hurricane belt), has a charming, rural, mountainous interior flanked by palm-shaded white-sand beaches. With its abundant boatyards and marine services, Grenada is now a thriving yachting community that many sailors return to season after season.

A consistent 15- to 20-knot breeze, sunny skies and the fact that most islands are within a half day’s sail mean the options are so vast, where to go really depends on what you’re seeking. With that in mind, here are the best anchorages in the Windwards. 

Best for ­Provisioning and Shopping

Le Marin on Martinique is a place where boulangeries and affordable French imports (yes, cheese and wine) abound. Many sailors make the hop from St. Lucia to Martinique just to go shopping. 

Provisioning is made easy by services such as Appro-Zagaya and Appel à Tous, which offer provisioning, knowledgeable advice, and delivery to the dock. Appel à Tous also has an app to place an order and mark the boat’s location for delivery, whether it be on a dock, on a mooring or at anchor. If fashion is what you’re after, anchor in Fort-de-France and explore the boutique-lined streets. A short bus ride away you’ll find La Galleria and Genipa, shopping malls with chic clothing and jewelry.  

Best for Diving and Snorkeling

The Tobago Cays, part of St. Vincent and the Grenadines, has a shallow, fringing reef that forms a gentle arc between ­sandy islets, dividing the crystalline, turquoise water from the plummeting Atlantic Ocean. Channels of white sand cut through dense reef, where damselfish dart in and out of their coral homes. Inside the reef, the anchorage encompasses a marine protected area frequented by green and hawksbill turtles. Don a mask and fins, and watch the turtles munch on seagrass, or venture out with the dinghy to Horseshoe Reef and tie onto a snorkeling mooring. (Scuba enthusiasts must dive with a local dive shop.) 

Carriacou, which belongs to Grenada, has one of the Caribbean’s most spectacular dives. Sister Rocks is northwest of Tyrell Bay, with black corals, soft gorgonians and ­iridescent-blue sponge vases that spill down the steep, sloping reef. The top 30 feet of ocean is often teeming with schools of baitfish or purple creole wrasse dancing in rays of sunlight. The current sweeps divers around the base of the islands as seabirds nest in craggy cliffs above. Harmless nurse sharks nestle into rocky overhangs below. This is an advanced dive with currents that can be especially strong. 

St. George’s is the capital on Grenada, an island where 15 wreck-dive sites scatter the southern coast. They include the “Titanic of the Caribbean,” the Bianca C. This 600-foot cruise ship sank in 1961. Advanced divers can explore the intact swimming pool at 120 feet deep. For beginners, the Veronica L, in less than 50 feet of water, is a favorite. The site is shallow enough for light to illuminate the coral-encrusted open cargo hold and the intact crane, making for a striking scene. 

Best for Hiking 

Sainte-Anne is a village on Martinique, providing access to more than 100 miles of hiking trails that are mostly well-designed and -marked. Sailors can try everything from an eight-hour round-trip hike up to the summit of Mount Pelée (about 4,580 feet above sea level) to moderate trails that follow the coastline. A trailhead for the nearly 17-mile coastal Trace des Caps is in Anse Caritan, just south of Saint-Anne. The trail links a series of interesting areas to explore, including Etang des Salines, a mangrove lagoon with winding boardwalks, and Savane des Pétrifications, an arid, coastal-desert landscape reminiscent of the moon. 

Soufriere and the Pitons on St. Lucia have terrain that can be moderately to extremely challenging. Gros Piton, despite its name, is the easier of the two pitons to hike, though the second half of the hike consists of steep stairs dug into the hillside. Petit Piton is shorter in elevation, but the climb is significantly steeper, much of it relying on the use of ropes to pull yourself up the cliffside. For less of a challenge and more-rewarding views, trek up Tet Paul, which offers spectacular views of both pitons, the bay below and the coastline on the other side.

Bequia’s deeply ­ingrained ­seafaring heritage is a major draw to the ­island, while ­sailors make the hop to Martinique for ­superb provisioning. 

Grenada’s inland section is lush and mountainous, with trails that cut through ­tropical rainforest, along mountain ridges, and into verdant valleys of cocoa, spice and fruit plantations. There are also 18 waterfalls and a crater lake to explore. Sailors can join the Grenada Hash House Harriers, an informal hiking group that lays a different trail and meets every Saturday afternoon. Upwards of 100 sailors, expats, locals and students gather for a jovial romp through the bush, and there are almost always carpooling options to get to the trailhead. 

Best for Artisans and Handicrafts

Bequia, in St. Vincent and the Grenadines, has a deeply ingrained seafaring heritage that includes whaling. It also has a long history of artisans and handicrafts, which means sailors can find great examples of scrimshaw (intricate carvings on whale bone) and model-boat building. A single boat model can take weeks to produce. Generations of skill go into everything, from selecting and felling the tree and curing the wood to painting and varnishing it, and threading delicate rigging. Most craftspeople set up stalls along the waterfront town of Port Elizabeth, where sailors also can find brightly painted calabash bowls, woven hats and baskets, coconut ­sculptures, and jewelry made from seeds. 

Best for Nightlife

Most islands in the Windwards have annual festivals or carnivals that are worth checking out. Grenada Sailing Week at the end of January is a Caribbean Sailing Association-accredited regatta with prizes, parties and nightly live music. Serious competitors and casual cruisers alike come together for the friendly competition. The Bequia Easter Regatta in April draws an even larger crowd. Traditionally, there are events for yachts and local double-enders, and the island buzzes with newcomers and returning champions. For music lovers, the St. Lucia Jazz and Arts Festival in May is the place to be. Within the past 30 years, its genres have expanded to include reggae, pop and gospel. An array of international stars take the stage for more than a week of live performances that go on into the wee hours. 

Best for Foodies

Fort-de-France on Martinique is the place to sample foie gras, caviar and escargot. Martinique has the best of the Caribbean’s fine French dining, with contemporary wine pairings and sophisticated presentations. Casual bistros and boulangeries on every corner overflow with fresh pastries. Even the simplest of lunches—a baguette layered with brie and sausage—is of a quality not found on the other Windward Islands. 

Bequia, in St. Vincent and the Grenadines, has restaurants along the waterfront of Port Elizabeth. The Belmont Walkway divides the turquoise bay from bistro tables and barstools. In the Windwards, this is the widest variety of restaurants in one area, including many casual Caribbean Creole options. For a sweet treat, try Marianne’s homemade ice cream in the picturesque waterfront courtyard of the Gingerbread Hotel. 

Best for Solitude

The Windward Anchorage at Mayreau, in St. Vincent and the Grenadines, has coral heads that dot a small barrier reef off the Atlantic coast. A deep channel runs along the rocky shoreline and opens up into a sandy bay inside the reef. With only the Tobago Cays in the distance, the wind blows unencumbered across the glistening sea. A single restaurant ashore provides the only connection to the outside world, offering the convenience of not cooking if the anchorage gets too rolly. 

Sandy Island is part of Grenada. Not to be confused with Sandy Island in Carriacou, it lies just off Grenada’s northern coast. The island is surrounded by a shallow coral reef. Boats need a shallow draft and skippers need a sharp eye to make it through the narrow, 5-foot-deep channel into this secluded, one-boat anchorage. 

White Island at Carriacou, also part of Grenada, has ­windswept vegetation that spills from a rocky pinnacle overlooking the Atlantic Ocean, tapering to a small ­peninsula of fine white sand. Both this island and its neighbor, Saline Island, are uninhabited, but Saline can be popular and crowded. By contrast, sailors usually have White Island to themselves, perhaps because anchoring can be difficult on the edge of the deep channel between reefs.

Best in a Big Blow

Grenada’s Port Egmont has a deep bay on the Atlantic coast. It takes a dogleg as the ­coastline transitions from rocky scrubland to thick ­mangroves. The entrance to the outer bay is reef-strewn and can be tricky, especially in a swell, but inside, there’s a deep lagoon that provides shelter from the surge. Port Egmont is the best option when offshore hurricanes disrupt the regular trade winds, and the prevailing wind and surge swing to the west. 

Tyrell Bay at Carriacou is a long and winding ­mangrove lagoon that’s one of the best hurricane holes in the Caribbean, especially for shallow-draft vessels that can make it through the ­4-foot-deep bottleneck into the inner bay. A wide, dense perimeter of mangrove forest protects the inner lagoon from heavy winds and surge. The lagoon is part of the Sandy Island/Oyster Bed marine ­protected area, and is accessible only under threat of a named storm.

Le Marin at Martinique is a deep, sprawling bay where mangrove lagoons finger off into 10 to 20 feet of water, deep enough for most yachts to tuck in and ride out a storm. The innermost bay is further protected from the wind by hills on either side. Anchoring in the mangrove lagoons is permitted only under threat of a hurricane, and the lagoons tend to fill up fast, as Le Marin is the yachting capital of Martinique. 

Best for a Last-Minute Haulout

Grenada has three large boatyards and many skilled, affordable technicians. If you’re coming from the north, and if time and distance are a major factor, then Grenada’s sister island of Carriacou is a day’s sail closer and might be the better choice. Carriacou has two haulouts, both in the main anchorage of Tyrell Bay, where most yacht services are located. Though Carriacou’s selection of services isn’t as vast as Grenada’s, parts can often be brought up within a day or two.  

Martinique is an option in the northern end of the Windwards. Le Marin is the island’s center of yachting. Though there is only one yard, it is large and ­well-equipped. Parts and technicians are top-notch, with a price tag to match. The nation’s capital, Fort-de-France, also has a boatyard. It is geared more toward motoryachts, and it’s a good choice for engine or mechanical issues.  

In all of these destinations, the time of year will affect space and availability. At the beginning and end of hurricane season (May and November), many boatyards are booked up months in advance. Some make space for a quick haul and launch in an ­emergency.

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We hadn’t really planned on spending New Year’s anchored off an uninhabited island with a glorious white sand beach in the Bahamas. But we got lucky. The original plan was to celebrate a land-based New Year with a large group of friends in Nassau, but once I found out that some cruising friends had anchored their 50-foot cat only a short ride away off Harbour Island, Eleuthera, and that they’d love to spend New Year’s with us, my wife Caroline, our friend Roberta and I jumped at the chance to leave the hustle and bustle of Nassau in our wake. 

Having endured several (rare) chilly days and (not rare) late nights in Nassau, the peace and quiet of a night at anchor off Harbour Island was blissful. The next morning, we hired a local captain to help us navigate the coral-ridden Devil’s Backbone channel between Harbour Island and Spanish Wells. Even with a chart plotter, local knowledge is essential to ensure safe passage through this tricky stretch of water. Our local guy was a particularly colorful character.

A-1 (yes, his name was A-1) hopped aboard with a wide smile and a mental stockpile of more one-liners than David Letterman. 

“Did you grow on Harbour Island?” I asked.

“Does Jimmy Carter like toothpaste?” he quipped. 

[Pointing at a spot on the chart] “Is the fishing any good here?” I probed.

“Is a bullfrog waterproof?” he joshed.

The stand-up routine (along with a healthy dose of island history and other random musings) went on for the entire passage through the coral maze. A-1 seemed to concentrate more on holding court than paying attention to the channel, but he got us through. We had arrived safely at Spanish Wells when A-1 shared his last bit of local knowledge, with a smile and a wink: “Nine times out of two, if you stay in the channel, you’ll be just fine.” And off he went.

We wound our way past the fishing town of Spanish Wells, set our sails in a following breeze, and plotted a course toward a group of tiny islands to the west. Our cruising guide offered little info on the area—and that’s what made it special. We discovered a perfect anchorage off an uninhabited white-sand beach. I’ve been on countless charters and cruises all over the world, but there was something unique about this little piece of Bahamian heaven. We were the only people in sight. It was the last day of the year. The water was crystalline. The sun shone in beams through dissipating cloud cover as the cold front moved out. The beach beaconed.

We swam the short distance to the shoreline where we discovered plenty of dry firewood. It was becoming clear how this impromptu “Bahamas-style” New Year’s Eve would play out. It was certainly a far cry from those swarming streets we’d left back in Nassau. We built a fire on the beach, just as the sun set during the last hours of the year, and we basked in its warmth under a blanket of stars. If the rest of this year is anything like the hours of the last one, it’ll be a very good year indeed.

(Edited original story from 2010)

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Long before Polar Sun, the Stevens 47 we’re cruising in Greenland, reached the Arctic Circle, we had left the night behind. The last darkness we saw was when we left Flowers Cove, in northern Newfoundland, at 2 a.m. to catch the downtide to Mary’s Harbour in Labrador. After that, with the bows pointed north into the Labrador Sea, though the sun would briefly set, the twilight endured until it rose again just a little to the right of where it had gone down.

“The Air Up There” – January/February 2023 issue

Barry and Sue Parkin had already lost one sail. They were really, really hoping that they wouldn’t lose another as they screamed toward the finish line during last year’s Oyster Palma Regatta off Spain’s Balearic Isles. Their No. 3 jib tore straight across and blew apart the second time they took the helm of their recently purchased Oyster 625, Papillon. It was a 2013 build, and the sails that came with it were probably a decade old, with levels of wear and tear that they were still sussing out. If you had asked the couple a few decades ago whether they would likely find themselves aboard that kind of a sailboat, they both likely would have said no. But now that they’re both 58 years old, with three of their four children out of school, they’re starting to think about sailing a lot differently.

“Making the Turn” – March 2023 issue

Quetzal slipped her mooring and steamed into the fog. Our job was to sail to Newfoundland, where our Viking voyage would commence—a northern track eastbound across the Atlantic eliciting parallels to the adventures of early voyagers. However, our first landfall was fabled Sable Island, a crescent of shifting sands 90 miles south of eastern Nova Scotia. It’s notorious as the “graveyard of the Atlantic,” and more than 350 wrecks form a necklace of tragedy. It’s also home to an unlikely herd of 500 wild horses. It’s also not easy to visit, so when Alan arranged a coveted landing permit, we had to stop.

“In the Wake of Vikings” – April 2023 issue

As a fellow cruiser gazed around the torn-up main cabin of our 1982 Stevens 47, Totem, his eyes grew wide. He asked a head-scratcher: “Why?” Why not buy a newer sailboat? Why take on so much work? Why not be anchored at a remote Pacific Island right now instead of dry-docked in a dusty shipyard? Because this boat—our home of 15 years through dozens of countries along a path around Earth, classroom for our three children, magic carpet to unimaginable experiences—is our Totem. This boat has cared for us, and so we cared for it, with a refit centered on its 40th year.

“The 40-Year Refit” – May 2023 issue

We were cruising through one of Desolation Sound’s towering fjords when the wind hit 35 knots. This type of a headwind is to be expected in this part of British Columbia, and it made me glad that I was—for the first time in my life—exploring a region not aboard a sailboat but instead aboard a 53-foot Grand Banks trawler with twin 650 hp engines. The term “powering through” took on a whole new meaning.

“Switching Gears” – August 2023 issue

In the realm of extraordinary adventures, the thrill of a circumnavigation stands tall, offering an unparalleled opportunity to experience by boat some of the most mesmerizing places on the planet—places other people can’t get to in cruise ships; places that are tiny, with no infrastructure, and you get to experience these things that others simply cannot. Combine the allure of such a voyage with the comforts of cruising in a group of like-minded sailors, and you have the Oyster World Rally. Over the course of nearly 16 months, 25 Oyster yachts’ owners and guests traversed approximately 27,000 nautical miles, visiting awe-inspiring destinations, creating cherished memories along the way, and forging bonds to last a lifetime through shared experiences, laughter, and the pursuit of a common dream.

“World Wanderers” – August 2023 issue

“Willie, call me as soon as you can. I bought a boat. I haven’t seen it yet. It’s in the middle of Florida. We have to get it out of the boatyard by Monday.” When I received the voicemail, I was racing a Melges 24 regatta in Miami, and I knew adventure was brewing. My father-in-law, Chris, had started with casual boat browsing online and progressed to the sight-unseen purchase of La Reine, a 23-year-old Beneteau 381. In the process, he had set in motion a journey that would take my wife, Kim, and me on a 50-day, 1,000-nautical-mile shotgun journey into the unknown—starting with getting the boat off the hard for him within three days. Little did we know, delivering this boat would teach us that even the best-laid plans are sometimes no match for fate.

“An Unexpected Adventure” – September 2023 issue

When Kirsten Neuschäfer decided to compete in the 2022-23 Golden Globe Race, she searched for a fast, safe and stable boat. She studied designs with a good ballast-to-weight ratio, and sought out a hull and rig that could withstand a hard beat to windward. She found Minnehaha in Newfoundland and knew that the tough, sturdy Cape George 36 was the one. The quick cutter with a generous sail plan met all of the official requirements—a production boat with a full keel, less than 36 feet long, designed before 1988—and a few requirements she had set for herself. After 235 days at sea, she crossed the line in Les Sables d’Olonne, becoming the first woman to win a round-the-world race.

“Solo Act” – October 2023 issue cover

I’m no Ernest Shackleton. I live in Hawaii, and I love the warm weather and clear blue waters of the tropics. Having done a little high-latitude sailing, I have to admit that freezing weather is not my favorite. My boat doesn’t even have a heater.  Yet here I was with Tracy, a surfing friend from Hawaii, ripping down Puget Sound at 12 knots under spinnaker, in the dead of winter. I had on about 10 layers, two puffy jackets, gloves, boots and a hat. I also had a huge smile on my face.

“A Winter’s Sail” – November/December 2023 issue

Steve Brown knows a thing or two about heavy weather. Throughout his sailing career, Brown and his wife, Trish, took on a four-year circumnavigation aboard their Oyster 56, Curious, sailed a 30,000-mile circumnavigation of the Americas—sailing north from Camden, Maine, and then an east-to-west transit of the Northwest Passage—and spent more than his fair share of time in the Southern Ocean. Brown is up for debating the superlatively inhospitable places on Earth. Along the way, there’s been brash ice and icebergs, rogue waves and drogues, penguins and polar bears. He’s a sailor who’s had the real-life experience of switching from gale-force storm management to survival tactics after conditions transcend control—just the kind of expert you want to lean in to for heavy weather sailing strategies that may save your life.

“Wicked Weather” – November/December 2023 issue

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The Lesser Antilles, on the eastern rim of the Caribbean Sea, is perhaps the finest watery hideaway for boaters on our planet. It’s impossible to exaggerate the magnificence of this sailors’ paradise. It is as if God and Walt Disney conspired to design the perfect cruising ground: perfect wind, perfect seas and, most of all, perfect harbors. 

And if all that weren’t enough, these harbors are also inhabited by joyous folks with wide smiles. The Caribbean is especially attractive for sailors who like to party—who desire to spend a decade or two hard aground on the mahogany reef. 

From a scientific perspective, the key to understanding this area is plates. The plates are tectonic. They bump into each other, stimulating partial melting of the plates above the subduction zone. These collisions result in arcs of ­volcanoes. In the Lesser Antilles, this happens at regular 40-mile intervals. 

I was confused about this when I arrived in the Antilles in the 1970s. That was, until I purchased a few cases of rum (at 82 cents a bottle) and met up with some farmers tending to their spices and herbs. Thus armed, I began exploring the islands from Culebra to Trinidad. 

Here’s what happens: Pressure builds and builds and builds until the pressure in the earth’s core is so great that it blows a hole along the crust of the tectonic plates. That’s when lava, which is boiling molten rock, flows out. If there’s enough lava, it forms a mountain. 

Often, mountains are pretty. And sloping mountains offer numerous advantages, not the least of which are regular rainfall and a calm lee to anchor behind. 

After an island is formed and few million years go by, the pressure builds again, and it blows a new hole along the same fault line. The happy result in the Lesser Antilles is an arc of islands running north-south that are a perfect daysail apart. 

From Anguilla to Grenada, a boater can awake, take two aspirin, have a beer for breakfast, and beam reach to the next island in daylight—with enough time to anchor, clear in, and be on barstool number one in time for happy hour. At least that’s how I arranged my cruising schedule for nearly three decades. 

Sadly, paradise isn’t ­perfect. In terms of weather, the eastern Caribbean is almost perfect, except for the two or three days a year when passing hurricanes attempt to kill you. 

This is why our fourth vessel was called Wild Card. On September 17, 1989, Hurricane Hugo blew away the entire deck of cards we’d been playing with, along with our beloved self-built 36-foot Carlotta.

But all things must come to an end, and every dark cloud has a silver lining. 

Take the story of ­28-year-old Ludger Sylbaris, for example. He was born in the ­fishing village of Le Prêcheur, Martinique, in 1874. By the turn of the previous century, he’d moved to Saint-Pierre and begun to party. Now, we’re not exactly sure what he did to get thrown in jail, only that it must have been bad. They put him in a dungeon and forced him into solitary confinement in a tiny, fortified cell whose only ventilation was a grate facing away from the mountain.  

Saint-Pierre was a bustling city at the time, nicknamed the “Paris of the Caribbean.” It was scheduled to have an election in a few days, so the city’s leaders didn’t want to evacuate the town just because the local mountain was acting a bit steamed.  

On May 8, 1902, at 7:52 a.m., a sailing ship had just left the waterfront and hoisted sail. Its crew glanced astern toward the shore, and the mountain blew, darkening the sky 50 miles in every direction. Between 28,000 and 30,000 souls were burned or suffocated. A few survived on the sailing ship, which proceeded to Fort-de-France to sound the alarm. 

It took four days for rescuers to arrive, but there was no one to save. Except for Ludger Sylbaris. After he was freed and asked what he was in jail for, he muttered something about parking tickets or whatever. He was, in any case, promptly pardoned by the local judiciary. 

Yes, the Caribbean can be capricious. 

One of our favorite stops was Plymouth on the island of Montserrat. That island was known as the “Emerald Isle” back in the day. The local rum shops on the beach had chalk signs out front that counted down the days until the next St. Patrick’s Day. The reason we liked this anchorage so much was threefold: 1) It wasn’t on the way to ­anywhere; 2) the harbor was rolly; and 3) because of the Beatles. 

We search out rolly harbors in popular cruising grounds because their anchorages are almost always deserted. In Montserrat, we hung with the crowd at the Agouti bar, unless producer George Martin of Beatles fame had someone recording. In that case, Mick Jagger, Jimmy Buffett, Sting, Mark Knopfler or Eric Clapton would sit in with the local reggae band until the wee hours. 

I mean, where better for Buffett to record his album Volcano?

The quaint town itself was delightful, as were its 4,000 inhabitants. It was impossible to get into trouble in Plymouth, where all the locals seemed totally blissed out. If a too-frisky yachtie overindulged in rum (“Rum is food” was our youthful motto) and started punching locals, the big fellas would take the first few blows with a puzzled smile, and then tie up the yachtie and return him to his vessel.

Fishermen would toss still-flopping grouper on our deck without being asked, or offer to sell us conch or lobster for pennies a pound.

Then, in July 1995, the Soufrière Hills volcano sent pyroclastic flows and ash across much of the island. By August 1997, the entire town of Plymouth was buried under ash, with only the tops of telephone poles and the red roofs of its tallest buildings showing. It was as eerie as it was sad, like an abandoned production set from an old Twilight Zone television episode. 

It’s impossible to exaggerate the ­magnificence of this sailors’ paradise. It is as if God and Walt Disney conspired to design the perfect cruising ground.

Each year, we’d sail in the lee of forbidden Plymouth during our passages south to avoid hurricane season. The silence would be deafening, especially with our regretful hearts straining to hear the once-vibrant reggae beat from the now-buried Agouti rum shop. 

Here’s a truism: The two best times to visit the Caribbean are yesterday and today. We went for a single season of high-wind sailing and stayed decades because of the joy. Nearly all of our 63 years of cruising have been spent in the tropics amid this best quality of life. 

Oh, the tales I could tell about a young, randy Foxy Callwood of Jost Van Dyke. Or the wild and crazy crew of Richardson’s Rigging on Tortola. Or Basil and his pretty boys of the Bitter End on Virgin Gorda. And where would sailors of the Lesser Antilles be without Tom Gerker of Parts and Power, or Charlie Cary of The Moorings in the Virgins, or Robbie Ferron and Bobby Velasquez on St. Maarten?

What rum shop other than Le Select on St. Barts would be successfully managed by a cute 14-year-old named Fast Eddie? We used to call the port of Gustavia “Star Harbor” because Bob Dylan, Harrison Ford and Raquel Welch were often seen wandering its narrow streets. 

Red Hook on St. Thomas was a nest of crazy sailors. Just to the west in French Town was Dick Avery—too busy building a monorail shipyard to notice that he’d invented bareboating. 

And surely there has never been a more famous, more unabashed nudist in the Lesser Antilles then Joel Byerley, skipper of Lord Jim, which was usually anchored in English Harbour, Antigua. Desmond Nicholson’s family brought English Harbour back to life.

Just the salt-kissed ink-slingers were amazing. Carleton Mitchell of the deep-draft schooner Caribee and the centerboard S&S yawl Finisterre wrote Passages East and Isles of the Caribbees, and won the Newport Bermuda Race three times in a row. Sailor Dudley Pope wrote the Lord Ramage series of novels and used to hang in St. Maarten’s Philipsburg harbor. Fritz Seyfarth, an early mentor of mine and author of Tales of the Caribbean, left his literary mark on Marina Cay in the British Virgin Islands. That’s after Robb White’s book Two on the Isle was written about the same sand spit. (The movie starred Sidney Poitier.)

No history of sailing would be complete without mentioning gymnast, ocean-racer and rum-worshiper Rudy Thompson. He not only would put a trampoline on wheels during St. Thomas carnival to do drunken flips over the live electrical wires in downtown Charlotte Amalie, but he also chartered his boat to Nobel Prize winner John Steinbeck. 

Just imagine how many more I could name if my ­short-term memory hadn’t been so ruthlessly abused.

Yes, the Caribbean is truly a movable feast—an unstoppable sailors’ party—and the best time to go is still right now. 

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Cruisers often bypass the small and lesser-­known southeastern Bahamian islands on their windward passage through the Exumas on their way south to the Caribbean. But they shouldn’t. Take the advice of Bruce Van Sant, legendary sailor and author of The Gentleman’s Guide to Passages South: “Don’t rush through the islands; they are too perfect.” So, Google up a map, friends, and follow along. 

Because the Bahamas are shallow, the water they occupy in the North Atlantic Ocean is that much lighter, and, frankly, more beautiful than the Caribbean Sea. You can sail for miles in 10 to 15 feet of the lightest hues of blues and turquoise, suddenly plunge into thousands of feet of dark blue ocean, and return to shallow turquoise toward the edge of the next island. The shelf acts and feels like a large V.

Conception Island is possibly the most beautiful of all the Bahamian islands and is only 45 nautical miles northeast of popular George Town on Great Exuma Island. As Van Sant suggests, to reach Conception Island, anchor the night before just south of George Town at Fowl Cay, an uninhabited island with a small swimming beach. This will save you 4 miles of motoring to exit Great Exuma. Raise your mainsail at first light, and a southwestern wind will give you one long, straight starboard tack to Conception Island. Uninhabited and pristine, the beach has water so clear, you’ll swear you can drink it. The whole island is less than 3 miles at its widest, and it’s low-lying like all the small Bahamian islands, making it almost unnoticeable on electronic or paper charts.

The Bahamas National Trust has designated Conception Island a national park, which protects conch, fish and lobsters. The coral heads and reefs that surround the island make for great snorkeling and diving. At high tide, an entrance to a creek two-thirds of the way down the western side allows you to dinghy into mangrove flats to see turtles, sharks, conch and other marine life.  

To relax, simply walk the deserted white sandy beach and let your mind wander in your escape to this stunningly beautiful anchorage. Or, from the deck of your boat, simply stare at the magnificent crescent-shaped beach, and imagine why no more than five sailboats and catamarans are anchored outside the island on any given day.  

Like this solo sailor, you might chance upon the only other sailors on the beach who happen to know the Bahamas like the backs of their hands. If you are fortunate, like me, they will buddy-sail with you 35 nautical miles northeast to San Salvador. There, anchor in deep white sand just east of the only town on the island, and your new friends will take you to their favorite coral head, where they will spear two huge spiny lobsters and share their spoils in a tasty dinner on their catamaran. For thanks, buy them cocktails the next day at one of the only open bars ­overlooking the beach.

Sparsely populated and somewhat larger than Conception, San Salvador Island hosts a handful of small resorts and, surprisingly, an airport that brings in daily flights from Florida. Still, it maintains the feel of a quiet and secluded Caribbean island. You can walk the traffic-free main road, and a friendly local might drive you to one of the two small grocery stores on the island. Much controversy surrounds the claim that Columbus made his first landfall in the New World at San Salvador Island, though a plaque on a building in the middle of town states that he landed there October 12, 1492.

From San Salvador Island, you can sail 30 miles southwest to Rum Cay in prevailing east winds. (An island with the word rum in it must be good.) Find yourself wind-protected on the absurdly beautiful, quiet and pristine Flamingo Bay on the western edge of the island. Your charts will show a submerged wreck, giving you fair warning to watch the depth and weave the coral heads using eyeball navigation. You can sleep soundly under a clear sky and shining stars in tranquil water. Among life’s finer experiences, one should enjoy a morning cup of coffee on the bow of a gently swaying sailboat in a warm, clear bay that is yours and yours alone. Dinghy to the deserted shore to create the only tracks on the white-powder beach.

On a rising sun, sail out of Flamingo Bay against an east wind to seek civilization around the corner to Port Nelson, the only inhabited town on the island, with reportedly fewer than 100 residents. With a handful of tacks, you will turn a 6-mile sail into 15 glorious sailing miles where you will see small flying fish burst out of the water to escape predators. At 30 miles in total area but still tiny in size, Rum Cay dwarfs Conception Island.

Port Nelson consists of a welcome sign and a government dock that accepts a mail boat three times a month. Near the dock, you might find yourself at The Last Chance, a ramshackle bar with sand floors, a pool table and a book rack. Kaye Wilson, the proprietor, will sell you a Bahamian beer for $3, a dozen eggs for $8 or a bag of frozen green beans for $6. She also will make you the tastiest burger for $12 and serve it in a foil wrap rather than on a plate. 

You might chat up the only other patrons, two Bahamian police officers also enjoying a lunchtime burger. Even though the island is crime-free and all residents know one another, the officers are on daily foot patrol. One might be wearing a polo shirt, while the uniform of the other is a ball cap and T-shirt that say “police.”

Don’t shy away from requesting a police escort to the only other open eatery, the Ocean View Restaurant, an establishment with wood floors that’s been proudly owned for 45 years by Ruby Bain. Her son will serve you a Guinness in a bottle delivered to the island on a mailboat. I watched in awe as she affectionately taught one of the officers a local song. After you share a beverage with the police and they insist that you stay on the otherwise sleepy Rum Cay for a weekend festival, you know that you have met some of the friendliest people on Earth.

To seek protection from an oncoming stiff and persistent eastern blow, depart Rum Cay at 4 a.m. and motorsail 30 degrees off an east wind to reach the western side of Crooked Island in daylight, some 60 miles southeast. You might find several sailboats and catamarans already there seeking shelter. 

At Crooked Island, it is impossible not to make new sailing friends, either on the beach or at Gibson’s Restaurant, where they seat customers, mostly sailors, cafeteria-style on a long table. They serve everyone the same delicious fare of locally caught fish, meat and vegetables.

Take the advice of legendary sailor and author Bruce Van Sant: “Don’t rush through the islands; they are too perfect.” 

At Crooked Island, you also might be lucky, like me, to find a stainless-steel spear pole washed up on the beach that you can use to spear your own lobsters. If you need diesel and water, motor a few miles to the Crooked Island Lodge and Marina, the only marina on the island. You might as well spend one night there instead of rolling on anchor in the big blow. The ­marina’s knowledgeable ­general manager will show you the nearby coral heads to hunt lobsters. (Using the ­newfound pole spear, this ­novice ­fisherman came up empty-handed, but the ­marina’s chef prepared a lobster dinner for me, the restaurant’s only customer for the night.)  

Sailors can do major provisioning at the marina for Bahamian beer, wine, local fish, vegetables, frozen hamburgers and delicious rolls. And what the marina does not have, the general manager will drive you 4 miles to find at the small grocery store. The marina is undergoing big renovations, including new hotel rooms, small cabana-like lodges, a new restaurant and a pool. It is also enlarging its jetty, so boats will enjoy a swell-free dock experience.

So far, you will have had days of pain-free windward sailing. That might end as you sail east toward the lightly populated Mayaguana Island, a staging ground for a ­southeast run to Turks and Caicos. If you have no time to wait for a favorable wind north of east, you might ­experience moderate bow-bashing and ­wave-crashing sailing to the small and uninhabited West Plana Cay, a good stop-off 43 miles toward Mayaguana. After you pass Acklins Island off your starboard and you steer 30 or so degrees south, the waves begin to behave, and you will reach West Plana Cay in calm conditions.  

Again, you will have all to yourself another beautiful ­turquoise-blue bay protected by an east wind, and you will ask why you are not ­spending long days there reading, beachcombing, fishing, ­sleeping, and just enjoying your escape from civilization. 

Last, the 37-mile east sail from West Plana Cay to Abraham’s Bay on Mayaguana will likely be similarly uncomfortable. Protected by a barely visible long stretch of coral reef, Abraham’s Bay will feel like you are ­anchoring in 15 feet of open ocean, but the overnight roll will be ­moderate and easy to handle. 

The next day, sail east in 14 miles of pain-free ­tacking across a small bay to Southeastern Point, where Van Sant suggests that you stage your departure to Turks and Caicos. From this point, you will have a better ­southward angle to sail a reach to Sapodilla Bay on the Caicos banks.

Damian LaPlaca is currently in Puerto Rico aboard his Jeanneau Sun Odyssey 39i Performance, Beckon.

The post Cruising the Southeastern Bahamian Islands appeared first on Cruising World.

I’m no Ernest Shackleton. I live in Hawaii, and I love the warm weather and clear blue waters of the tropics. Having done a little high-latitude sailing, I have to admit that freezing weather is not my favorite. My boat doesn’t even have a heater.

Yet here I was with Tracy, a surfing friend from Hawaii, ripping down Puget Sound at 12 knots under spinnaker, in the dead of winter. I had on about 10 layers, two puffy jackets, gloves, boots and a hat. I also had a huge smile on my face.

This was shaping up to be an ideal adventure, filled with solitude and unexpected experiences. It was also some of the best sailing I’d done on my Jeanneau 509, Kāholo. And it had all started with simple necessity: I had to move the boat to get new canvas.

In 2021, I had sailed ­new-to-me Kāholo 5,000 miles, across the Atlantic and the length of the Caribbean, from Portugal to Panama. While soaking under the torrential rains of Panama, I realized I definitely needed new canvas. Once we got to the Pacific Northwest, I learned that Iverson’s Canvas in Olympia, Washington, had a yearslong waiting list. And its team would not travel to your boat. Like the Soup Nazi in Seinfeld said, “No soup for you!” Unless you were ­prepared to travel.

Olympia is on the South Sound near Tacoma, 80 miles south of my winter berth in La Conner, near the San Juan Islands. Although I managed to secure a spot on Iverson’s busy schedule, the only date its team could do the work was in mid-February, the coldest month of the year.

Well aware of the shifting weather systems in Puget Sound, I stacked things in my favor by leaving plenty of time to choose a weather window. As luck would have it, a high-­pressure system was set to fill in, bringing a favorable, but very cold, northerly wind. To get ready for the next day’s northerlies, Tracy and I made a short sail out to the historic town of Coupeville on Whidbey Island, where we spent time in a warm pub with the colorful local crowd that had replaced the summer tourists. Well-fortified against the cold, we paddled back out to lonesome Kāholo, the only anchor light in the anchorage.

Leaving Coupeville early, we had a serene reach south in calm water, all alone, jibing back and forth across Possession Sound under an asymmetrical spinnaker. It was challenging sailing in shifting winds, amid evergreen-­covered islands down Whidbey, the second-longest island in the United States, after New York’s Long Island.

The wind began to build as we neared the bottom of Whidbey. The helm felt lively. Somewhere around freezing, the wind sent a chill right through me. Adding another puffy jacket at the helm, I was quite comfortable but looked like the Michelin Man.

We blew right past the mooring I’d had in mind for the end of the short winter day, not to mention the alternate destinations I’d marked off in case the weather or the gear failed to cooperate. This was no ordinary sail, and we were having too much fun. We continued south toward Seattle.

Passing the southern tip of Whidbey Island, we sailed into the comparatively open water of Admiralty Inlet. Both the seas and the wind began to build. Now we were reaching at 12 knots with more than 20 knots of apparent wind. This was the upper limit for the spinnaker. The boat was ­handling well, but I could feel the rudder loading up as the boat leapt through the following seas. Rounding up in this wind with the spinnaker would mean taking it down in pieces. Breaking seas to windward alerted me that the wind was still building in the exposed waters of Admiralty Inlet. As the saying goes, any fool can put up a sail, but it takes a sailor to know when to take one down—and I’d ­apparently left it a bit late.

“Tracy!” I called out. “We need to get that spinnaker down. Now!” 

As Tracy hustled forward, I brought the boat downwind to hide the spinnaker behind the main. Tracy tried to douse the sail, but the sock refused to come down. The spinnaker sock lines had become tangled after so many jibes. I managed to balance the boat on a deep reach, with the seas slewing her around and the spinnaker flailing behind the main. I set the autopilot, praying we wouldn’t wrap the sail around the forestay, and jumped forward to help. We managed to untangle the lines while the autopilot miraculously kept us safely off the wind. The sock ­finally slid over the unruly beast and we dropped the sail to the deck with a sigh of relief. After that battle, we were no longer cold. The wind increased to the point to where the working jib was now plenty of sail, and we surfed south to Port Blakely, just across Puget Sound from Seattle on Bainbridge Island.

We arrived as the sun set and the lights of Seattle came alive in a purple sky. We could see the huge marinas of Elliott and Shilshole bays, housing thousands of boats. Yet we were alone, swinging at anchor in a quiet cove at the end of a perfect weekend sailing day. Finally, one other sailboat joined us: a singlehander on his 30-foot Wauquiez. 

With the setting sun, temperatures dipped well below freezing. Luckily, we had thick down comforters on the bunks to keep us warm. In the morning, I found water pooling on the floorboards, something no captain wants to see. Assuming we had a freshwater leak in one of the pressurized lines, I pulled off panels to reveal the hullsides. They were running with water. In freezing temperatures, comparatively warm moist air inside the cabin condenses on the cold hull of the boat “like a cold can of soda on a hot day,” as one sailor described it. I immediately invested in a dehumidifier for use at the dock. The proper solution while underway would, of course, be a diesel heating system. 

The northerlies were still blowing the next day, and we raised the spinnaker again, doing an outside jibe back and forth down serpentine Colvos Passage to Gig Harbor. For an outside jibe, I bring the boat directly downwind, jibe the main to put the boat wing on wing, and then completely release the working spinnaker sheet, letting the spinnaker flag in front of the boat. I then turn the boat through the wind, onto the new tack, and haul in the leeward spinnaker sheet, which is led around the bow on the outside. I can do this singlehanded, and it works like a charm as long as the sheets don’t get snagged on anything. Sadly, they often do, which requires a trip to the foredeck to unsnag them.

Gig Harbor was where we’d planned to meet the team from Iverson’s Canvas. A lively harbor town shadowed by Mount Rainier—with several marinas, a fishing fleet, a strong paddling scene, and lots of maritime history—Gig Harbor was named in the 1800s for Capt. Wilson’s gig, or rowboat, brought into the narrow entrance for shelter. The town is home to Gig Harbor Boat Works, which builds traditional gigs from modern materials.

It was amazing to watch Kyle and Mike, two guys from Iverson’s. They installed custom, large-diameter stainless, and patterned the entire dodger and Bimini top with plastic sheeting, all in a day. They said it would be two weeks for me to receive the dodger and Bimini top, but they were back a day early. The new dodger transformed the cockpit, with better visibility and clear windows. It felt as though I’d been upgraded to an ocean-view home after cowering under an old tent for years. It wasn’t cheap, but it was money well spent.

As luck would have it, sailing north back up Puget Sound was also a downwind run. Southeasterlies are quite common in winter, often associated with the approach of a low-pressure system. This was exactly the case I encountered: An approaching low was sending me 15-knot southeasterlies. I jibed back and forth up the sound, this time singlehanding because Tracy had flown back to Hawaii. Often, I would tangle the sheets on some obstacle on deck or on the anchor, and I’d need to hustle forward to free it. On my last jibe across Admiralty Inlet, on a layline for Port Townsend, I noticed the unmistakable T-shaped mast of a submarine steaming at me en route to the naval yard at Bremerton. Two oceangoing tugs and two US Coast Guard vessels were in escort. Soon, the Coast Guard politely hailed me: “Sailing vessel Kāholo, I see that you are making tracks for Marrowstone Point. We request that you keep as close as you feel safe to the shore. We will be turning right, into your path.” Good thing I was on a layline, with good speed, and didn’t plan another jibe. The consequences of something going wrong were too great.

An old friend, veteran bluewater sailing instructor John Neal with Mahina Expeditions, met me at the dock at Port Townsend. He showed me around the bustling boatyards and introduced me to his favorite sailmaker, Port Townsend Sails, and riggers, Port Townsend Rigging. These are family operations where attention to detail and craftsmanship are the rule. John says that he can get 50,000 to 55,000 miles (two circumnavigations) on a single main and jib built by the craftspeople at Port Townsend Sails, who, by the way, are all women. 

I set out on foot to see the boatyards at Port Townsend, the premier wooden-boat building and repair region on the West Coast. It’s a dynamic place where the next generation of shipwrights learns traditional skills at places such as the Northwest School of Wooden BoatBuilding. I wandered around the yards, amazed at vessels like the 133-foot San Francisco bar pilot cutter Adventuress, built in 1913 and still sailing here. 

Port Townsend is famous for its annual wooden-boat show, but what seems to have escaped worldwide notice is that Kirsten Neuschäfer, the South African sailor who recently became the first woman to win the Golden Globe round-the-world race, sailed a Port Townsend boat: a 36-foot, 1988 fiberglass-hulled version of a traditional 1930s design built by Cape George Marine Works. Her boat was among only three boats to finish the grueling race without pause for repairs, and it survived 235 days at sea around the tempestuous Great Capes—and with Neuschäfer managing to rescue a skipper whose boat had sunk.

Continuing my stroll through Port Townsend on this cold, blustery afternoon, and seeing a small sign advertising “sails and canvas built and repaired” on an old wooden building in the harbor, I ducked into a shop called The Artful Sailor. Engulfed by the smell of tar, hemp and linseed oil, I found Emiliano Marino and Pami-Sue “Salty Sue” Alvarado practicing the ancient art of marlinspike seamanship. The late-afternoon light streaming in through the windows made it look like a scene from an old Dutch painting.

Only in Port Townsend could a sailor encounter a nuclear submarine, see a 1913 schooner and meet a couple practicing traditional marlinspike splicing, all in the same day.

Unfortunately, my luck ran out with the weather, and I sailed the 30 miles up to Deception Pass and to Kāholo’s La Conner slip in full foul-weather gear, in cold, drizzling rain and variable winds. The ending was a bit of a letdown, but overall, this had been an unforgettable voyage, precisely because it had happened in the dead of winter.

Not that I am planning any Shackleton-esque small-boat crossings in the Antarctic, but at least now I understand the beauty of a winter’s sail. Next on the my shopping list? A diesel heater.

Tor Johnson is an award-­winning photographer and writer who has shot 16 covers of CW, so far. He grew up sailing the world with his family.

The post A Winter’s Sail appeared first on Cruising World.

My wife, Kati, and I are among the million boaters who helped to make Florida the state with more registered boaters than any other in America. We’ve lived in Orlando for three decades, cruising our 50-foot schooner, Britannia, all around the sailing haven and beyond to the Bahamas. Florida really is a paradise for those of us who love to take to the water. For so many boaters, it can be hard to imagine living anywhere else.

But last year, Kati and I reached a pivotal moment: We needed a fresh start in a new place, even if it meant bidding adieu to all we held dear. 

So, we looked to the north. Yes, there were drawbacks to this idea. Venturing north would elongate the return trip to the enchanting Bahamas, a paradise we longed to frequent. We didn’t want the biting chill of winter to necessitate an entire wardrobe overhaul. Nor did we care to wrestle with the tedious task of winterizing our boat’s engine and generator each fall. We weren’t seeking wholesale change, but instead an adjustment; we still wanted to live in a haven that would allow us to sail Britannia year-round.

A nautical map of the Eastern Seaboard drew our attention to a vast expanse of water on the eastern shores of North Carolina—Pamlico Sound, accompanied by its slightly smaller northern sibling, Albemarle Sound. Intrigued by these alluring destinations, we embarked on a weeklong exploration.

The picturesque town of New Bern greeted us, its charming streets steeped in British and Colonial history, adorned with an array of delightful restaurants and three adjacent marinas. Nestled at the convergence of the Neuse and Trent rivers, the town would give us easy access to Pamlico Sound, which sprawls 60 miles in length and 20 miles in width—a vast playground for sailors, replete with winding rivers, meandering creeks and quaint waterfront towns. The mighty Pamlico River also beckons sailors, enabling navigation for 40 miles up to the town of Washington—­affectionately dubbed “Little Washington” by the locals.

Among the renowned destinations on the Outer Banks—guardians of Pamlico and Albemarle sounds—is the legendary Kittyhawk, where the Wright brothers took their first flight. Sailors too are familiar with the treacherous Diamond Shoals off Cape Hatteras. This entire part of the Atlantic coastline has earned the moniker “Graveyard of the Atlantic.”

Between the splendid realms of Pamlico and Albemarle sounds, Roanoke Island emerges. It’s where the first British settlers planted their feet in 1587, predating the Mayflower’s storied voyage by 32 years. Being natives of the United Kingdom, as we strolled through towns with stores called Ye Olde British Tea Shoppe, we felt an instant kinship with these once-­British colonies. Moreover, adorning the 150-mile stretch of the Outer Banks are some of America’s most pristine, untouched beaches—a true testament to nature’s majesty.

We also discovered a delightful oasis from Florida’s high marina fees in the form of city docks, which this part of the country generously offers to visiting boaters for a few blissful days. Aboard Britannia, we were saved from shelling out nightly sums ranging from $60 to $100. 

Then again, if we wanted marinas, Pamlico and Albemarle sounds had them: a dozen marinas within Pamlico Sound alone, each conveniently located a mere fraction of the 70-mile journey we used to undertake from Orlando to Cape Canaveral in Florida, sometimes just for a fleeting day of maritime pleasure. And marina prices here were a mere third of what we paid in Florida. 

We also chanced upon Fairfield Harbour on the Neuse River. It’s just south of New Bern, evoking images of a miniaturized Fort Lauderdale. Canal-style branches sprawl across the main lagoon, with an array of homes that have private docks and picturesque gardens. 

The allure proved ­irresistible for Kati and me. As self-­employed individuals—me freelancing as a boating writer, Kati operating her real estate company—we found ourselves with minimal hindrances to relocating to North Carolina. And this location would bring us 400 miles closer to our daughter and grandchildren near Charlotte.

Within Fairfield Harbour’s confines, two yacht clubs awaited our arrival, including Blackbeard Sailing Club and its marina. The warm embrace of the yachting community enveloped Britannia. In our short time exploring, we forged friendships with more fellow yachties than we ever did in Florida. 

In addition, the specter of falling prey to a catastrophic hurricane weighed far less heavily on our minds here. Hurricane Florence brushed the region in September 2018, causing severe flooding, but unlike in Florida, such occurrences were rare. We had gotten Britannia out of Florida before the devastating hit from Hurricane Ian in 2022, but even being unscathed, we thanked our lucky stars and considered the idea of a home base where such devastation is less likely to occur. North Carolina’s Pamlico Sound dances to the tune of ­prevailing winds, ebbing and flowing in response to their whims. During strong gusts, a surge of 3 feet might materialize—a mere trifle when compared with the dramatic tides of the Atlantic and the kind of storm surge that wipes out whole waterfronts along the Florida coast.

Our minds were made up. We listed our Florida house for sale, and a buyer materialized within a fortnight, sealing the deal in just five weeks. Our new abode is at Fairfield Harbour, nestled amid verdant woods—albeit without waterfront access or a private dock. The truth is, we couldn’t afford to be picky. But we can still dream and keep an eye on the local market.

After sailing Britannia northward to her new haven, I secured a sizable dock rental from the homeowners’ association. Our boat’s new home port is conveniently located within walking distance of our abode. The cost is a mere fraction of what we paid in Florida.

We’ve been here for a while now. During the winter, snowfall greeted us, a rare occurrence after years spent in Florida’s warm embrace. I relished the opportunity to join our grandchildren in building a snowman in our front yard—an experience that had been absent from our lives for far too long. Such simple pleasures only add to the wonderful feelings we have in our newfound coastal haven.

As of yet, we have embarked on only preliminary ventures into the sound, cautiously exploring the places we discovered during our earlier visits. Of course, we intend to explore more as we further settle into our new locale. From secluded anchorages to quaint waterfront towns, our journey through the Southern seas will undoubtedly be one for the annals—a tale of discovery, rejuvenation and the serendipitous sojourns of a Southern sailor.

If you too find yourself yearning for a respite from the unpredictable climes of the tropics and the frigid North, let the winds carry you to the pristine beaches of the Outer Banks, the enchanting shores of the Pamlico and Albemarle sounds, and the warmth of Southern hospitality.

We’ll be among the boaters waiting to greet you with a warm smile and local ­knowledge.

The post New Cruising Grounds: Switching Home Ports From Florida to North Carolina appeared first on Cruising World.

We were cruising  through one of Desolation Sound’s towering fjords when the wind hit 35 knots. This type of a headwind is to be expected in this part of British Columbia, and it made me glad that I was—for the first time in my life—exploring a region not aboard a sailboat but instead aboard a 53-foot Grand Banks trawler with twin 650 hp engines. The term “powering through” took on a whole new meaning.

I’ve enjoyed more than a few sailing adventures in my lifetime—not just racing America’s Cup boats, but also on expeditions to remote places including Antarctica, Cape Horn, Sable Island (off Nova Scotia) and Norway’s Svalbard. I’ve completed trans-Atlantic crossings on sailboats too. Now in my 70s, I decided to try a trawler charter with NW Explorations, which is based in Bellingham, Washington. Our crew included my wife, Janice, who has cruised extensively in Maine and on the Chesapeake; longtime friends David and Christy Elwell, from Florida, who had cruised this area twice before this trip; and Kitty Mountain, also from Florida, but a veteran Desolation Sound cruiser. We were all of similar age, and we all had ­experienced our share of health issues in recent years. Somehow, letting a reputable charter company do most of the planning and make sure the boat was in good working order seemed like a reasonable compromise this time around.

It’s hard to keep me away from a helm, and I particularly enjoyed the solitude of many hours spent running the trawler from the upper deck. The views are fantastic from this perch, with the mountains along Desolation Sound rising 5,000 feet straight up out of the water. I thought about how, when the wind was exceedingly light, it would have been difficult to make progress under sail. Instead, we cruised onward at 9 knots, burning 6 ­gallons of fuel per hour. There was no hurry. We were having too much fun.

Desolation Sound is surprising in so many ways. Often, we would find a suitable cove to anchor, only to discover that the depth next to the shore was 600 feet. We’d have to look elsewhere or tie up to a few trees or rocks. And although the water was deep, it was surprisingly warm during our September cruise. The water was also, often, ours alone, with few other boats around.  

It’s counterintuitive that it could be so (relatively) easy to get to a place so remote, but that’s precisely what the five of us—a perfect-size crew for a trawler this size—had done. We had picked up the boat from the charter base in Bellingham and then cruised over to Port Sidney, Canada, to complete the immigration and customs process for Canada. The New York Yacht Club had organized a few rendezvous of which we took advantage (it’s always fun to compare notes with the crews aboard other yachts), and we were far from the only out-of-towners who were awestruck by the scenery.

Desolation Sound’s remoteness also gave us a liberating break from internet and cellphone service. We stayed busy with hikes, reading, and in-depth conversations about world affairs, the economy, and our grandchildren. We played spirited nightly games, took occasional naps, and focused on some of my favorite things: navigating and steering. The boat had an autopilot, but I like having my hands on the wheel and my eyes all around. Every few miles, an interesting sight or object would appear: a pod of whales, tidal rips, the ever-changing shoreline. The farther north we sailed, away from the impressive waterfront homes of Vancouver and the San Juan Islands, the more remote the scenery got.

After we anchored each afternoon, we enjoyed dinghy trips where we found all kinds of nifty things. We poked our bow into small coves, intriguing creeks, marshes and lagoons. We went ashore and worked our way through thick brush. Climbing was hard work, as was walking along the rocky coastline. We never saw bears or cougars, but we did see fascinating birds in the skies. The osprey clutches a fish with its face into the wind, making flight easier. Who knew?

Two cruising guidebooks were particularly helpful: Desolation Sound & the Discovery Islands by Anne and Laurence Yeadon-Jones, and Cruising Guide to British Columbia Vol. 2: Desolation Sound and the Discovery Islands by Bill Wolferstan. As a rule, the authors ­caution mariners to be mindful of tidal rip currents between islands. They’re correct. A few times, it was nice to be able to power up the engines and motor through passages that would have been challenging under sail. All kinds of boaters embrace the challenge, though; we encountered several flotillas of kayaks, including on one of the windy, rainy, chilly days. They waved happily as we steamed past.

I enjoyed Prideaux Haven, a scenic, protected cove that’s crowded during the summer months but had just eight boats scattered around on the day we arrived. The entrance is narrow and shallow, with Mount Denman off in the distance at about 6,500 feet high. For a (brief) minute, I thought we should attempt to scale the peak. The tidal range was about 18 feet, which meant anchoring with care. In one cove, we looked for the remains of an indigenous peoples’ village. We found only rocks, shells and sand, but it was fun to look around.

A few times, it was nice to be able to power up the engines and motor through passages that would have been challenging under sail.

At other spots, we encountered the fishing and logging industries that dominate this region. Signs ask mariners to reduce speed when passing the fish traps and working zones. On Toba Inlet, we watched a ground crew cut trees while a helicopter hovered over the trunks and grasped them with a heavy-duty clamp. At times, two or three trunks were hoisted together. They were moving 60 to 80 trunks per hour.

We followed the advice of the guidebooks at the Yuculta Rapids, a stretch of water with fast-moving currents at the northern end of Desolation Sound. The books strongly suggest transiting during periods of slack water; we experienced fierce rapids about one hour after slack water. Whirlpools, steep and choppy waves, and overfalls were evident as we motored through. Dent Island had a ­seating area where you could watch the churning rapids. We had a great dinner there, and, the next morning, a full ­breakfast before continuing on our expedition.  

I had to smile at some of the waterway names. Two of my favorites were the Hole in the Wall passage, which is a small opening connecting the Okisollo Channel to the Calm Channel, and the One and Only Inlet.

Along the Toba Inlet, we found ancient images of land animals and a sea serpent painted on the shoreline rocks. Equally as mesmerizing was a nearby 150-foot waterfall near picnic benches. One scene was more spectacular than the next.   

At one small general store, I found ­candy bars. My plan was to have one treat per day. The next afternoon, behind the wheel, I was enjoying my 3 Musketeers when the rest of the crew started asking, “Where’s mine?” I took some heat for the next few days, until we came across another general store where I was able to secure a larger supply, along with Raisin Bran cereal for one of our crew who loves it.

We also took comfort in our trawler’s solid hardtop and upper-deck chairs. I had to smile, remembering how, when I was 6 years old, I used to sit on the side of a small boat and marvel at the water gurgling alongside the hull. Here on Desolation Sound, I was still marveling at the water passing by. This instinct to appreciate the view has never left me, no matter whether I’ve been racing on the Irish Sea or from Rhode Island to Bermuda. I thought about my first sighting of the Antarctic peninsula with ice-covered peaks jutting into the sky, the surprising beauty of the Mediterranean, and the lush beauty of the Caribbean. The size of Chesapeake Bay is surprising, as are the endless destinations on the waters of New England. 

I have enjoyed all of it. What a nice life we have, being on the water. A few days after our expedition on Desolation Sound, I started to wonder, What’s next? 

CW editor-at-large and award-winning writer Gary Jobson is a Hall of Fame sailor.

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“Willie, call me as soon as you can. I bought a boat. I haven’t seen it yet. It’s in the middle of Florida. We have to get it out of the boatyard by Monday.” 

When I received the voicemail, I was racing a Melges 24 regatta in Miami, and I knew adventure was brewing. My father-in-law, Chris, had started with casual boat browsing online and progressed to the sight-unseen purchase of La Reine, a 23-year-old Beneteau 381. In the process, he had set in motion a journey that would take my wife, Kim, and me on a 50-day, ­1,000-nautical-mile shotgun journey into the unknown. 

Starting with getting the boat off the hard for him within three days.

Two days later, I got my first sight of the boatyard where La Reine was waiting. Row upon row of deserted boats covered in various shades of mossy growth stretched as far as I could see. Imagination turned to panic as I drove past the first derelict hulls and pulled through the front gate.

As I entered the boatyard, heads popped out of companionways covered in fiberglass dust and paint. The boats in this part of the yard were notably more seaworthy, and a ragtag crowd was lovingly working on them.  

La Reine had a fresh coat of paint that made her shine, and a suite of new electronics gave her a modern feel. As a professional racer who has seen my share of collisions and repairs, I was very aware that the shiny new cosmetics might mask something far more daunting. I pushed the possibilities from my mind and set to work. 

The Caloosahatchee River makes up the western stretch of the Okeechobee Waterway, which connects the tranquil Gulf waters of Fort Myers to the Atlantic Seaboard at Port St. Lucie. We had not yet been able to secure a reservation in a marina on either coastline, so the plan was to take the boat a few miles downriver toward Fort Myers, and then leave her in Port LaBelle Marina to buy ourselves enough time to install safety gear and make a game plan.

That afternoon, one other boat was ceremoniously hoisted from its resting place in the yard in preparation for an adventure at sea. The excited young couple had spent the past two years on the hard fixing leaks, working on the engine, refitting plumbing, and everything in between. Briefly, the thought crossed my mind that La Reine should spend a few more months in the yard to go through all the systems, but it was too late for that. Whatever issues the new paint hid would be revealed soon enough.

After a three-hour round-trip drive to Fort Myers to acquire provisions for my first night on the boat, I returned to find that the stove wouldn’t light, so my quesadilla dinner became a cheese and tomato wrap. After dinner, I discovered that the toilet wouldn’t flush, thankfully in time to head up to the marina bathrooms.

Kim arrived early the next morning. After a pit stop to ­purchase parts, we started up the diesel on the first try. Our adventure was underway.

The first day was smooth motoring. Kim navigated the canal, and I watched YouTube videos to learn how to dissect the plumbing. As I wrapped up installation of a new pump and valve, we arrived at our first lock. The friendly lock operator walked us through the procedure, and the conditions were calm, making the process easy. When we were ready, the back gate closed, the front gate cracked open and dropped the water level 14 feet, and we were on to the next section of canal.

At Port LaBelle that evening, we were greeted by an alligator floating lazily past the entrance. We cut the drone of the diesel, so the only sounds left were nature: plentiful bird life and the distant moos of cows. It was the quintessential Southern evening. We still didn’t know where we were headed, but for the next few weeks, this would become our launch pad for the projects needed to make it to the ocean, and whatever lay beyond. 

We had only a few short days in Port LaBelle before I had to head back to work for a week, and Kim had a trip planned with friends. We crammed in as many projects as possible, with the expectation that we’d be headed to the ocean the next time we saw the boat.

When we returned to Port LaBelle, Chris had settled on a summer marina at Jekyll Island, Georgia. Meanwhile, Kim and I were plotting a one-month detour through the Bahamas. We would head east on the Okeechobee Waterway, then south to Miami and up through the Bahamas, then to Georgia. We didn’t have any marina reservations, but we felt that there was no better way to get to the top of the waiting list than to show up.

As soon as Kim arrived, we transferred a mountain of boxes we’d ordered online from the marina office onto the boat, and we bid farewell to Port LaBelle. With a nice following wind, we unfurled the jib for the first time and retraced our tracks from only a week before.

After about an hour, we arrived back at the lock that we had previously dropped down and prepared to float back up. “Ready?” came the voice of the operator. We thought we were.

As the back gate closed, I noticed that the fenders were slightly too far apart. The freshly painted rail of La Reine came to rest just inches from the cement wall as the front gate opened and water rushed into the lock. The boat seesawed at the mercy of the floodwaters. 

With my gaze fixed on the tiny gap between the rail and the wall, I wrestled with the dock line, fighting to avoid grinding off the fresh coat of paint. Minutes seemed like hours, but eventually, the water calmed and the boat came to rest. Miraculously, the rail was unscratched. 

For the rest of that afternoon, we motored lazily up the canal, past Glades Boat Storage and up the river to Moore Haven, where we spent the night on the city dock.

The morning was full of beauty, with golden sunlight pouring down on swampy vegetation and animal life. Alligators, turtles, lizards, and birds of all varieties seemed to wake with the sun and escort us down the next stretch of the ditch. 

By late morning, we passed through Clewiston and reached the entrance to Lake Okeechobee, where we set a course through the narrow channel. By noon, land slipped from sight and the wind built to the midteens. Our jib was deployed, and our adventure seemed to be in full force.

Kim was at the helm when the steady, rhythmic knocking of the diesel began to fade. At first, I thought one of us had bumped the throttle, but power quickly faded to an idle thrust. I spend a lot of time around outboard engines in my job as an Olympic sailing coach, but the diesel was a new beast. This felt like a gas issue, but the gauge read three-quarters full.

Kim turned us head-to-wind while I hoisted the main and cut the engine. The wind was puffing at nearly 20 knots and, luckily, carried us downwind toward the far lakeshore, but we knew we would need the engine to get through the lock on the far side. Kim drove while I went below to put on my mechanic’s cap.

After about an hour, I had drained some sediment out of the fuel filters. I was cleaning out the air-intake manifold when Kim called down: “I can see the lock getting closer. The waves are getting bigger. What are we going to do?”

I poked my head back up. The channel markers for the lock were getting close. 

We cranked the engine, throttled up, and La Reine plowed forward. 

“Sails down and fingers crossed—all we can do now is hope that it doesn’t die again,” Kim said with a worried look. 

We hailed the lock operator. The wind was now blowing a steady 20 with a lumbering, lumpy chop. The lock operator came on the VHF radio: “Conditions are rough, but it’s not getting any better. Let’s get you through. When you get inside, let me close the gate before you go to the wall so that the chop can die down.”

If the engine died now, we’d have major problems. We carefully nosed into the lock, with the boat pitching wildly from the chop. 

“Be ready with a mobile fender in case I lose control,” I told Kim. 

As the gate swung closed behind us, the engine held, but even with full power, I was fighting hard to keep the boat under control. The bow swung left, then right, at the mercy of the wind, so I tried to keep the stern centered to buy enough time for the chop to subside. 

“That’s it,” came the voice of the lock operator. The chop was still big, but we were fully committed, so I took a deep breath, tried to relax, and waited patiently for the bow to swing. As the next puff took hold, the boat rotated 20 degrees, lining us up for a nice approach to the wall. I hit reverse, praying that the engine would hold just 60 seconds longer.

In the end, it was one of our smoothest lock passages. While the lock operator commented on our excellent boathandling, I told myself, Better lucky than good.

I started to relax as we exited the cement box into the ­tranquility of the canal on the other side, but no sooner had we passed the final gate than the bridge ahead stole my focus. This 49-foot railroad crossing controlled the navigational height east of Lake Okeechobee. 

We radioed the operator for a final check on water-level height. When we told him we were 48 feet tall, he replied, “Don’t quote me on this, but I think you’ll probably make it.”

The adrenaline took hold again.

Back at Port LaBelle, I had gone up the rig and measured that we should have a foot of clearance above our mast, but seeing the bridge in front of us, my imagination ran wild. I envisioned a westbound motorboat trying to squeeze through the bridge at the same time as us, with its wake bouncing us into the top of the bridge. We figured that every inch mattered, so, using a hammock, we rigged up a seat for Kim on the end of the boom. As I swung her out over the water, the boat heeled 5 degrees to starboard. I had calculated that this should buy us 6 extra inches of clearance.

We went as slowly as possible, with the hope that impact at these speeds might give us a chance to save the rig, but the ­approach was agonizing. Hanging over the water, Kim worried that she might have a date with an alligator if things went south. 

At the last moment, I threw the boat in neutral. As we glided smoothly through the crossing, I looked up. Was it just me, or was the antenna on top of the rig tickling the bottom of the bridge? No, just my imagination. Elation. We were through.

We laughed and smiled and felt like heroes. We had avoided the lengthy western route through the Keys, and the sun was shining.

We didn’t notice the first few raindrops. All afternoon, I had been tracking the cumulus development to the north, and while the fluffy white pillars had grown into thunderheads, the radar showed no sign of southern movement. While we’d been preoccupied with the lock and the bridge, though, the system had veered sharply. Within minutes, I found myself diving for my foul-weather gear in pelting rain.

No sooner was I dressed than the engine died again.

Kim rushed below to grab the windlass controller. The crackle of thunder and lightning in the distance was getting closer. I swung the bow head-to-wind in the lee of a thicket of trees and, with the last of our momentum, did my best to estimate the swing of the boat in the narrow canal. 

“Drop 20,” I called, glancing at the depth gauge. Kim put down 20 feet of chain as the boat started backward. 

With the anchor set, we scrambled below and closed the hatches to wait out the rest of the squall and continue working on the diesel. 

Later that evening, La Reine slipped down the glassy canal as the towering cumulus above the forest reflected golden oranges contrasting with ragged, dark grays. La Reine’s diesel, alive once again, buzzed gently under my feet. The air was still thick from the rain, but it was cool now that the storm had moved off into the distance, having washed away much of the sweat, grease and stress that marked our first big day of delivery.

As we pulled into a slip just before the final lock of the trip for the night, I was reminded that man plans and God laughs. Of all the scenarios I had run through in my head, the leeward shoreline lock with a dead engine had not been one of them.

The next day, we headed for the Atlantic. We geared up, ­tethered in, and headed out of Stuart in a beautiful 15-knot northerly for La Reine’s first true sailing test.

The first hour was all smiles. We surfed the waves, reaching and winging our way down the coast. Through the afternoon, the breeze built and more rolling waves began to make Kim feel sick, so we set a course for an inlet a few miles down the coast. Before we could make it to the calm water, however, we heard a popping noise, and looked up to find a large hole in the luff of the main. A seam of old stitching had given out, and rotten threads on either side looked ready to give way too.

The mainsail blowing out wasn’t something that we could have predicted, but as soon as it happened, we made the best of the situation. Kim took the helm and spun us into the wind while I reefed the main to the second reef point. This confined the hole in the sail to the folds of the reefed slab, allowing us to continue down the coast at a good pace as we motorsailed to Hillsboro Inlet at Pompano Beach.

For the next few days, the clear-blue Miami water replaced the murky green twists and turns of the Intracoastal Waterway, and we began to feel one step ahead. As we wound our way through the juxtaposition of wild nature and intensive urban ­development, we were able to secure a mooring ball, schedule a mechanic to service the engine, and book an appointment to have the boat sized for a Bimini top.

In the final stretch, we navigated intense Saturday traffic in Miami: lavish yachts, loud music, and crazy chop from ­reckless boaters. As we turned into the calm waters of Dinner Key Marina, sweet relief washed over us.

Champagne in hand, we video-chatted with Chris, telling him we’d made it and that La Reine was in one piece. We spent the rest of the evening reliving our endless snafus, laughing and smiling. It was amazing how much life we had lived in just four days.

What had we learned? No matter whether you order your boat new or find one online, plans will eventually fail. And when they do, the real adventure will begin. 

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The mid-May sun was surprisingly hot as we spun into the wind, idled the engines, and hoisted the big roachy main aboard San Fredelo II, the Sunsail 404 catamaran that would be home for the next five days. Next, we rolled out the genoa and bore away to a beam reach, leaving provisioning chores, briefings, crew introductions and the Marina Agana astern. 

Sailing, at last—in Croatia. A longtime entry on the proverbial bucket list was about to be scratched off as my sailing pal and trip organizer, Josie Tucci, vice president of marketing at Sunsail, steered us eastward and out of the narrow bay toward open water dotted with islands. Near the helm, her brother, Jason, and I trimmed in the sheets and tidied up as we began making way. To port, I could see cars on the coastal highway, headed north from the international airport in Split. To starboard, the rocky, brush-covered shoreline rose to meet a sky that was fairy-tale blue. Already, my colleague, photographer and drone junkie Jon Whittle was snapping away. How could he not? The sights were otherworldly in this centuries-old corner of the Adriatic Sea.

Around us that Sunday morning, the crews aboard nine Sunsail monohulls were going through similar drills, as one by one they raised sails and pointed their bows toward Milna, on the island of Brač, the flotilla’s first-night destination, where a gin-and-tonic reception awaited us.

I’d never sailed in a flotilla before, but already, less than a day into it, I was enjoying the concept of exploring a new destination with a helping hand, if you will. Earlier that morning, after a buffet breakfast of eggs, sausages, fruits, and doughnuts at the marina’s restaurant, skippers, and crew gathered in a shady spot to meet Sunsail’s flotilla captain, Samantha “Sam” Algero; hostess Ellie Riccini; and “Drago,” the team engineer. This trio would be on hand to assist and advise 24/7. When it was time to go, they’d be the ones handing us our dock lines. And when we arrived at a new location, their boat, Hvar 1, would already be tied up. They’d be waiting to take stern lines as skippers nervously (at first, anyway) backed in to moor stern-to at each new village.

“Slow is pro,” Sam reminded us frequently the first few landings.

Ellie too dispensed practical info. “Keep the boats tidy,” she urged. “A tidy boat is a safer boat.” And, “Beware the sea urchins.”

At that first briefing, Sam and Ellie outlined the week ahead: daily skipper meetings at 0900, lunch where you like, and each evening a different destination with a suggested time of arrival. At night, there were organized events to attend—or not. Wednesday, we were free to sail wherever we liked, so long as we all regrouped in time for dinner on Thursday.

They went over the fine points of Lateral Navigation System A (red and green buoys are opposite where they would be in the United States), safety issues, and local weather to watch. The bura is a gusty northeast wind that brings clear conditions. The jugo: southeast breezes with rain. The maestral northwesterlies tend to build in the afternoon. 

And these words of caution: “If you didn’t eat it, don’t flush it.” Holding tanks were to be emptied 2 miles offshore, and there was a 100-euro fee to fix a clogged head.

Alrighty, then. Duly warned.

But best of all, their review of the charts greatly ­simplified finding the Croatian place names that were difficult to ­pronounce, tough to understand, and even harder to spell.

Off to the Islands

Josie, Jason and I had spent Saturday afternoon provisioning at the nearby Tommy’s market. For a few coins, you could borrow a shopping cart to deliver groceries to the boat. We stocked up on lunch meat and breakfast fare, Croatian wine, and Ožujsko, a local beer. That evening, we had dinner at the marina and sat on San Fredelo’s tramp watching the moon rise over the opposite shore. The water was still, and the reflection of the square stone tower at the head of the harbor was crystal-clear.

Sunday turned out to be a perfect day to regain our sea legs, with a northerly breeze in the midteens sending us on our way. We stopped for a late lunch and anchored in the pretty little harbor at Stomorska, on Šolta, a point that was about halfway into our 18-nautical-mile sail. The anchorage allowed an imposing view of the towering mountains that rise above metropolitan Split. Ashore, a handful of fishing boats sat idle, and we saw but a few folks moving about amid the distinctive white villas with red-tile roofs.

From there, it was an easy run to Milna and the Marina Vlaška. As Josie backed the cat toward the quay, Jason and I stood on either transom with boat hooks in hand. We handed our stern lines ashore, and the Sunsail team held up bowlines for us to grab and take forward. The ropes are sunk when not in use, and are led from shore to anchors in deeper water. It was an amazingly drama-free operation.

Once we were settled, we grabbed swimsuits and found a nearby rock from which to jump. The seawater was cool but refreshing, making a hot shower at the marina afterward feel all that much better. Then we headed up the hill, past olive trees and stone terraces, to claim our gin-and-tonics, and to chat with other crews as they came and went.

At sunset, we walked a mile or so along the shore road into town. On the way, we passed a street vendor and stopped to buy four garishly colored Croatia ball caps that quickly became our team hats. In the town center, a large, weathered stone church was lit up, along with other ages-old buildings. Behind them, we spotted more steeples draped in light. We found an open table at a small pizzeria and washed down our slices with tasty local wine.

Of course, we posed for photos with the colorful, whimsical ice-cream-cone statue we passed on the way back to the boat.

Relic of War

A look at the charts reveals that along this part of the Croatian coast, long, thin, mountainous islands run roughly west to east from the open Adriatic, as though some ancient creature drew fingers though terra firma, allowing the sea to run in between.

On Monday, we didn’t have a lot of wind as we motored out of Milna and turned southwest to navigate the channel between Šolta and Brač, and turned again southeast to follow the coast. We passed numerous marine farms and inviting anchorages, but we’d already decided that our lunch-stop destination would be a small bay a few miles south, where a submarine base dating back to when the country was part of Yugoslavia is carved into the hillside. Once we’d found the cove and anchored, we launched our inflatable and took a ride inside the long, narrow tunnel once used by naval vessels to avoid detection. Rather than seeing warships, we found cool relief from the sun-splashed bay. Today, fishermen use the rock-lined safe haven to tie up their skiffs. During our visit, there wasn’t a soul around. Instead, small birds darted about, their shrill chirps echoing off the rock walls.

The cove was quite protected. As a few others in the flotilla fleet arrived and dropped anchors, we took turns exploring on the two paddleboards we’d brought along. 

That afternoon, a lazy breeze picked up from the northwest, and San Fredelo ran before it as we headed for the harbor at Jelsa, on the island of Hvar, across a body of water marked on the chart as the Hvarski Kanal. After a morning of motoring, all aboard welcomed the sail, but the dead-downwind heading proved both crash-jibe prone and slow. Eventually, we kicked on the motor again to make the harbor in time for a 1600 tie-up. After all, wine and hors d’oeuvres at a waterside restaurant, organized by Sam and Ellie, awaited us. 

Jelsa lies near the midpoint of Hvar’s north shore. Its harbor is a relatively square body of water, protected by stone jetties. Wide, flat stone walkways around the waterfront give the place an open plaza-like feel. When we arrived, several flotilla boats were already tied stern-to, but Capt. Sam directed us to an open spot, and her crew scrounged up a plank for us to use as a passerelle. 

The restaurant, the iconically spelled Me and mrs Jones, was on the far side of the harbor. Our stroll there took us past palm trees and weathered stone buildings—some white, others a faded pinkish color. Inside the restaurant, the front room had been cleared out to make space for a table covered with wineglasses, carafes of red and white wine, and trays piled with appetizers made with anchovies, shrimp, and assorted meats and cheeses. Soon, the stone-block-lined room was packed. 

After an hour, the crowd thinned and the staff began setting tables for dinner. Jason and I took a half-empty carafe of red and sat at a table outside with a couple from the flotilla who were sailing aboard a Jeanneau 34. Steve was from England, Josephine from Hong Kong. Prior to the pandemic, these longtime friends would meet at various locations around the world for sailing vacations. This was their first time together since the global shutdown. They planned to keep the boat at the end of the week, and sail up and down the coast a bit longer. Like sailors everywhere, we talked about weather, memorable voyages and, of course, our current adventure, which they were finding to be quite social compared with their usual visits to quiet, remote anchorages.

As we were about to leave, a pair of women rode up on bikes and sat at the table next to us. They pointed to the road winding up the towering mountains that form a spine atop Hvar and said that they’d just come over them from the other side of the island. No wonder they were ready to sit down and quench their thirst.

That evening, we strolled up into the hillside town from the waterfront. The stone streets were polished smooth by centuries of foot traffic, the narrow lanes between buildings too tight for cars. The sounds and smells from the open-air Konoba Nono restaurant were irresistible. Its barbecue was excellent, and we topped it off with glasses of rakija travarica for dessert. The strong-tasting liquor, often made of plums and herbs, is a Croatian delicacy and must at least be sampled, in my humble opinion.

I say “sampled” because in abundance, it can lead to unexpected consequences. After dinner, Jason returned to the boat while Jon, Josie and I continued to explore. Our ramblings took us past age-old churches and through tight, twisting alleyways, past homes with laundry left out to dry in rocky courtyards. Eventually, our footsteps led us to a tavern, which led to Croatian beer and then more rakija. We were left spellbound by the sweet folk melodies that a woman named Anna and her male vocalist partner sang as they leaned against the bar, drinks in hand. When the bar closed, we lingered outside, talking with the singers. He had to work in the morning and said goodbye. Anna? Well, we followed her to the small bar she owns and sat talking until dawn, then went with her to watch the sunrise from a beach.

That’s the thing about a sailing trip to Croatia. The people are as warm and friendly as the islands are lovely. It was easy to strike up a conversation with just about anyone. Most Croatians we met spoke English. Every storekeeper had a smile. The owner of an olive shop, recommended by a waiter and contacted by phone one evening, agreed to open early the next morning so that we could buy delicacies to take with us. Strangers couldn’t wait to tell us why we had to visit their favorite spot. Everyone had one. It’s easy to fall for such charms.

Off On Our Own

It’s perhaps not surprising that we were the last boat off the quay Tuesday morning. Not to worry—we had just a 12-nautical-mile hop to the west along Hvar’s north coast to reach the protected bay off Stari Grad, one of the oldest towns in Europe. The little wind we had as we left Jelsa was on the nose, so we chose to motor instead of sail. It was yet another lovely little adventure on the water, complete with dolphins. Across the channel, the mountains on Brač were a patchwork of earth tones and greens, the hues of olive trees and gluhi bor, a black pine that covers the arid landscape. Ferries crisscrossed the channel, and we passed numerous small fishing boats and saw flocks of birds working the water roiled by baitballs off in the distance.

By 1430, we were tied up to yet another stone quay in a snug ­harbor surrounded by a bustling town. We moored just in front of the town’s municipal showers, which were handy. From there, Jon and I walked a half-mile or so along the quay to restock at a Tommy’s market, and then met the rest of our crew for a late lunch.

Back at the boat, we sat under the cockpit Bimini top in a feeble attempt to evade the stifling afternoon sun, and chatted with the crew aboard the flotilla boat moored next to San Fredelo. 

We dined ashore that evening at Nook Stari Grad, a restaurant recommended by a passerby. The woman waiting on us had ­recently returned from living in Rochester, New York, and we met another member of the waitstaff who’d been lured back from California. Both were tickled to be home. The Nook’s chicken curry was spicy, the beer was cold, and the open-air seating under an arbor of trees was absolutely delightful. We walked the long way back to the boat, through more narrow stone streets. On the ­waterfront, there wasn’t a ripple on the harbor, and even in the town center, the quiet was interrupted only by the occasional dog bark.

Wednesday was our free day, and a bura was forecast for the afternoon. After looking at the chart and cruising guide, we decided to sail southeast along the coast of Hvar and across the Pakleni Kanal to the island of Sveti Klement. 

We set sail as we left Stari Grad and tacked upwind around the western tip of Hvar. From there, we were able to bear away and reach down the middle of the channel between the two islands. Early on, the 10- to 12-knot breeze was perfect. But as the morning progressed, the wind clocked and turned gusty so that before long, the sea was covered with whitecaps. At the eastern end of Klement, we turned south and sailed through a marked channel that runs close to the island, and then doused sails as we spun to the west to motor a short way up the island’s south coast to Vinogradišće, a small, protected cove that’s home to Laganini Lounge bar & Fish house and a small mooring field just off its dock. After a swim, we headed ashore for lunch at a table overlooking the water, and watched two self-described influencers shoot photos of one another over glasses of bubbly. As we finished our dishes, a motorboat arrived to whisk them away, shooting selfies all the while.

We spent a lazy afternoon swimming off the boat and, before sunset, walked a short distance across Palmižana, where we caught a water taxi to old-town Hvar. The wind was still gusty, and it was a wet ride back across Pakleni Kanal but well worth the trip.

Hvar is a vibrant city, the largest on the island, with a long history of being a trading and cultural center. The city was part of the Venetian empire from the 13th to the 18th century, and a naval base as well, with an imposing fort above the waterfront.

As in the other towns we’d visited so far, we walked. From the harbor, we hiked up a seemingly endless flight of stairs toward the fort. Shops, hotels, restaurants, and residences lined the steps and stone alleyways that led off to either side from occasional landings. We found a small, rock-walled cafe where we ordered a tableful of appetizers rather than a full dinner: sausages, meats and cheeses, octopus, sardines and the like, along with olives, anchovies and grappa. Afterward, we walked some more. A plaque on a monastery we passed dated the stately white-stone building to 1472. In one shop, we spotted a merchant armed with a knife, standing behind a huge slab of prosciutto held upright on an iron stand. You bet we had him carve off slices to take back to the boat, along with a couple of bottles of cherry grappa. 

At 2130, with minutes to go before the last water taxi ­departed for Palmižana, we hustled back down flights of stairs to the waterfront, arriving at the dock with little time to spare. Over the course of the evening, the winds had died, and we had a lovely ride back to Klement, with the night sky ablaze with stars.

Last-Night Raft-Up

After a swim and coffee Thursday morning—and, how could I forget, spinach-and-tomato omelets—we motorsailed east along Klement’s south coast, winding through Soline Bay and the outcrops of rocks at the end of the island. From there, we reached northwest to Šolta and anchored in the bay at Tatinja—called Uvala Tatinja Lonely Paradise on the chart.

Lonely it was. There were only two other boats anchored there and just a couple of houses onshore. In front of us were centuries-­old stone terraces built into the hillside and groves of trees; ­behind us, nothing but the deep-blue Adriatic Sea and a cloudless, deep-blue sky overhead.

That night, we anchored stern-to on a rocky shore in Šešula, with the entire flotilla rafted together in front of a small restaurant. The bay was quite large, and we went exploring by dinghy, motoring alongside new friends Lawrence and Cathy in theirs. In a distant corner, we found a fish farm before turning back. In the afternoon, Sam and Ellie organized inflatable races, with two-person crews paddling their hearts out for bragging rights. 

Dinner that night was a group affair, and afterward, the party moved back to the boats, where the monohull crews gladly came to visit our big, roomy cat, helping us clinch Best Party Boat honors at the farewell dinner Friday evening.

The next morning, Josie, Jason and I walked along a coastal trail lined with flowering bushes and the occasional modest house, and came to a small village, Maslinica, where we found a working marina, a couple of shops, a spot serving breakfast, and a 20-foot-long yellow-submarine statue with photos of John, Paul, George and Ringo staring out of porthole-like circles on its side. It was a sleepy tourist town, and a sign near its center said that it had received numerous national tourism awards, including one in 2017 for being the best Authentic Coastal Destination.

On our return that morning to Marina Agana, we had the wind on our nose again, so we took our time motoring toward the mainland. We made a detour to visit the long, deep bay at Vinišće; the shore was built up with houses on one side and an industrial-looking pier on the other. Instead of stopping for lunch, we raised the main and sailed across to the open bay off Trogir, anchoring for a spell to eat and swim.

And then, at last, it was time to return to the marina where we had started. On the dock, once the boat was squared away and ­before we took a taxi ride into the hills for one last group ­gathering, I chatted with Bill Truswell, an Irishman in his 70s, who, with his wife and two sons, had enjoyed this week of ­flotilla-style sailing.

“Stress is something I’m no longer needing in life,” he said.

I couldn’t agree more. 

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