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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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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An autumn passage from the US East Coast to the Caribbean is one of sailing’s great adventures. Every fall, hundreds of sailing yachts make this voyage—alone, with a buddy boat, or in a rally. No matter which route you choose, it’s approximately 1,500 miles, taking eight days to two weeks of sailing time in the Atlantic, over the Gulf Stream, and through the Bermuda Triangle. There’s a high probability you’ll be hit with a 30-plus-knot cold front and a couple of squalls before you pick up the trade winds for a few of days of delightful beam-reach sailing into the islands. Here’s a look at three ways you can head south.

Option One: From Newport, South

Being from Maine, I used to sail down to Newport, Rhode Island, for the boat show in September, and then leave for Bermuda when the forecast was favorable. At that time of year, the weather windows are usually wide open. I’d keep an eye on the tropical weather and, if no storms were brewing, I’d leave, knowing I’d get to Bermuda in five days, before a hurricane could form and beat me there. 

More recently, I’ve taken to joining Hank Schmitt and other delivery captains on the North American Rally to the Caribbean, which departs from Newport in late October. Schmitt has been organizing the NARC Rally for the past 24 years and is planning on turning over the tiller to the Salty Dawg Sailing Association in 2024. 

This Newport departure leaves on northwest winds of 18 to 25 knots. With the wind astern, it’s 200 nautical miles—about 33 hours—to the Gulf Stream. Pick a waypoint on the north wall of the stream, west of the rhumb line. By the time you exit the stream 10 hours later, the 3-knot current will have swept you 30 miles east, putting you back on the rhumb line. With the stream behind you, it’s time for T-shirts and shorts. 

Bermuda is just 360 nautical miles ahead—two and a half days away. You’ll see Bermuda’s lights hours before landfall. The last time I made this trip, in 2021, we got there in three days and 20 hours, with winds no stronger than 25 knots all the way.

Wait in Bermuda a few days fixing stuff, reprovisioning, taking on fuel, socializing, enjoying the island, and resting up for the 850 miles from Bermuda to St. Maarten, or 950 miles to Antigua. Five to eight days in length, this second leg of the voyage will be a great deal more enjoyable. The worst is behind you.   

This stop in Bermuda is my ­preferred route, even if I depart from Chesapeake Bay.

Option Two: Departing the Chesapeake

Leaving from the Chesapeake means that the Gulf Stream is only 100 miles offshore. You’ll be across it within 24 hours. Don Street, the old guru of sailing, says that if you are already south and west of Newport, your best bet is to depart from the Chesapeake, or farther south. (Street’s first published article was advice on sailing south, 60 years ago in Yachting, September 1964.)

Leave on a northwest cold front, and you’ll have the wind abaft the beam for two or perhaps three days.

This popular route is a 1,500-nautical-­mile east-southeast arc out into the Atlantic before turning south. It’s a seven- to 12-day nonstop voyage, with two to six days of motoring through the Bermuda Triangle. While this route bypasses Bermuda, each year, a few boats stop there for fuel, rig or sail repair, or to just break up the long voyage.

Boats need to have fuel for at least five days of motoring, and food for three weeks. Each year, a few boats run into problems with steering, the rig, fuel or seasick crew, and they retreat. Better to be prepared.

If the weather has you bottled up in Hampton or Norfolk, Virginia, you can motor down the Intracoastal Waterway. The rule on the ICW is 63/6 (meaning a 63-foot mast height to get under the bridges and a 6-foot draft so that you don’t run aground). In three days, you’ll be in Beaufort, North Carolina, a wonderful town with three marinas. From there, the Gulf Stream is only 50 miles offshore. You’ll be across and into warmer weather in 15 hours, and then it’s a similar course as those departing from the Chesapeake.

From Beaufort, you can also meander farther down the ICW, or sail slightly offshore inside the Gulf Stream, ducking into ports when necessary, all the way to Florida. 

Once in Florida, you have your pick of departure ports: Fernandina, Palm Beach, Fort Lauderdale. In late November and December, watch the weather carefully. 

“When a good hard norther threatens, leave 24 hours before,” Street says. “Place a pound of butter on the main cabin table, head east-southeast until the butter melts, and then turn south. Then, head southeast, and you might actually arrive in St. Thomas on track all the way. These are the same sailing directions that have been given for probably 300 years.”

If the weather in the Bermuda Triangle is unfavorable for making the offshore voyage, there’s the Thornless Path. 

Option Three: The ThornLESS Path

If you are departing from anyplace in Florida, and if the winds in the Bermuda Triangle are nonexistent or contrary, then hopping down the Bahamian chain is an option. You can sail down the chain either outside to the east or through the chain itself. The latter requires stops to anchor each evening. Joan Conover, president of the Seven Seas Cruising Association, has sailed the Thornless Path a few times and favors it as a route south. Bruce Van Sant’s book The Gentleman’s Guide to Passages South maps out this route in detail.

The Turks and Caicos is a jumping-off spot for the slog south and east to the Dominican Republic, Puerto Rico, the Virgin Islands, and the Eastern Caribbean. Traditionally known as the “Thorny Passage,” it’s a windward bash against the trades, current and swells, but it can be done; just stay clear of Haiti. There’s a process that savvy skippers use of sailing at night along the coast of Hispaniola.

In the Dominican Republic, you’ll find the Caribbean of 50 years ago. YouTubers have posted videos on finding the ports of entry, crossing the Mona Passage, and understanding the route along the south coast of Puerto Rico. Noonsite.com has up-to-date information on port entry, marinas, services and restrictions.

Getting Ready

No matter which route you decide to take, the journey starts with planning and preparation. My pre-departure checklist is eight pages long. Here are a few things to consider.

The boat: Is it seaworthy, capable and ready? Is it designed and built for an offshore voyage, or for coastal cruising or racing? Inspect everything from stem to stern, masthead to keel, and hire a ­surveyor to catch things you’ll miss. Your insurance company might insist that you have a recent survey anyway. Get it done early so that you have time to make repairs. Be there to watch and ask questions. Also have a professional rigger and an experienced diesel mechanic do ­inspections. Grease the steering system, and tighten the bolts in the quadrant. Find and test the emergency tiller. Is the rig set up for offshore, with an inner stay on which to hoist a staysail, or a Solent stay? Can the boat be reefed and hove-to easily? Are the bilge pumps adequate? Is all the safety and person-overboard gear up to date? 

Supplies: You’ll need to carry enough fuel for five days (100 hours) of motoring, plus drinking water and provisions for three weeks. Remember to bring enough toilet paper. I forgot once. Had to turn back.

The crew: Have at least two or three seasoned sailors with you who don’t get seasick, can stand a solo watch, and know what to watch for. I find crew on sailopo​.com, which is free. Your insurance company might want to see résumés from you and each crewmember, and might insist that you hire a pro skipper. If you want to crew on somebody else’s boat, a two-week training voyage can cost $4,000 to $6,500.

The weather: No matter the route, the weather tells us when to go—or not. Rallies provide a pre-departure weather briefing and daily updates at sea. You can retain your own weather-routing service, or you can do your own forecasts underway with an online service such as predictwind.com or windy.com.

Resources: In addition to the resources listed throughout this article, I find it helpful to have copies on hand of Street’s Cruising Guide to the Eastern Caribbean and Transatlantic Crossing Guide by Donald M. Street Jr., World Cruising Handbook by Jimmy Cornell, Sailing a Serious Ocean by John Kretschmer, Offshore Sailing: 200 Essential Passagemaking Tips by William Seifert, Handbook of Offshore Cruising: The Dream and Reality of Modern Ocean Sailing by Jim Howard, and Ocean Sailing: The Offshore Cruising Experience With ­Real-Life Practical Advice by Paul Heiney. 

David H. Lyman is an award-winning writer and photographer based in Maine.

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Dreaming of the wind in your hair, the sun on your face, and pure sailing exhilaration in the environs of an exotic destination? Perhaps it’s an annual quest. Or a lifelong dream. But where to begin? Once you’ve identified the destination, finding a reputable charter company, well-maintained boats and staff with intimate, local knowledge can be a daunting task.

What if you love the water, have spent many hours on your favorite lake or river but are not comfortable heading out on the ocean with your family all by yourself? With a bareboat charter out of the question and luxury-sailing-yacht charter options often out of reach, for many, the dream of sailing the big blue has remained just that—a dream.

But fear not, ye wistful ocean lover, whether you are a neophyte or an expert mariner, Dream Yacht Worldwide is uniquely positioned to facilitate those sailing dreams.

Founded in 2000 in the Seychelles, Dream Yacht was the vision of founder Loïc Bonnet, who set out to revolutionize the charter industry by making sailing an accessible activity for sailors and nonsailors alike. What began with six sailing charter vessels cruising the idyllic waters of the Indian Ocean has expanded dramatically over the past two decades.

Today Dream Yacht offers nearly 1,000 sailing yachts from 34 feet to 58 feet and power and sailing catamarans in 50 of the world’s most exquisite cruising destinations. What’s even better? Dream Yacht is purposefully designed to provide sailors of any skill level the sailing experience of their dreams.

On Location

With Dream Yacht Worldwide, you can think beyond the BVI and Caribbean milk runs, although there are plenty of Dream Yacht charter vessels in these areas too. Dream Yacht Worldwide offers more choices of destinations around the world than any other yacht charter company. This gives exceptional peace of mind that lets you know that no matter what destination you choose next, the charter vessels will be well-maintained and offered at the same high standard of service you’ve come to expect of Dream Yacht based on the sailing grounds you’ve already come to know. 

In fact Dream Yacht has so many destinations to choose from that if you decided to go sailing for a whole year, you could explore new cruising grounds every week without visiting the same islands twice, unless you wanted to. Imagine gunkholing in Thailand’s remote coves and anchorages, diving off the bow in Tahiti, or sailing under a fjord’s waterfall in Norway. 

Picture yourself savoring the cuisine and soaking up the Mediterranean culture while meandering along the coastlines of Italy, France, Greece or Spain. Step back in time in Croatia or Turkey, or battle the elements in the rugged seas of the Atlantic off Brittany or La Rochelle. With many European countries not just sporting one, but three or four Dream Yacht bases you will get the opportunity to constantly sail where the wind and weather is best for sailing at that time of the year.

Perhaps you envision catching the elusive green flash from the aft cockpit in a beautiful Caribbean or Bahamian destination, watching the sunrise, with your morning coffee, along the US eastern seaboard, or charting a new course in the Sea of Cortez or the Whitsunday Islands. From St. Martin to Sweden, the destinations offered by Dream Yacht will inspire you to expand your sailing horizons.

Dream Yacht’s unique premise is simple. Once you’ve selected a destination, it’s time to identify your preferred vacation style. Dream Yacht offers sailing experiences to suit every cruising preference, from bareboat and skippered to by-the-cabin and fully crewed charters or long-term rentals.

The Bare Essentials

When all you need is a reliable, well-maintained vessel that you can handle yourself, a Dream Yacht bareboat charter is for you. With a bareboat charter, you take care of your own provisioning, plan your own itinerary, and spend your days exploring at your own pace. The caveat? You must be experienced with the type of vessel you plan to charter and in some countries need official documentation regarding your skills. If you plan to explore the Mediterranean, for example, you will need your ICC certification. 

Aye Aye, Captain

Leave the anchoring and the chart plotting to the captain on this vacation with a Dream Yacht skippered charter. Perfect for those with little to no sailing experience—or for those who simply want to sit back and enjoy the world go by—a skippered charter brings a professional and experienced captain on board to man your vessel. Dream Yacht’s captains all have professional sailing experience and vast local knowledge of their respective destinations.

All the Bells and Whistles

For the complete all-the-frills experience, consider a fully crewed yacht charter. With this option, you and up to 11 guests can set sail on a large private monohull or catamaran yacht, and be catered to from the moment you step foot on board until your departure. Dream Yacht Worldwide hand-picks your professional crew to handle the itinerary, provisioning and daily cabin service, and you will enjoy water toys, a fully stocked bar, and scrumptious meals prepared to your culinary preferences by your own personal hostess.

Dream Yacht’s “easy crewed” product offers a bridge between a skippered and fully-crewed charters for groups of up to 10 family members or friends traveling together. You decide how little or how much service you need. Easy crewed charters are currently offered in select destinations in the Mediterranean, the Seychelles, Tahiti, the BVI, and Martinique.

Space for Two…or a Few

If a whole boat is more than you need, you may be most comfortable with a cabin charter, which is a shared-vessel experience that gives you a single or double cabin with a private en suite in the company of other like-minded travelers. The cabin charterers share a full crew, a set itinerary, daily meals with drinks and snacks, and the option for additional onshore excursions.

A Quest for Sustainability

As pioneers in their industry Dream Yacht just started adding a selection of electric sailing catamarans to their charter fleet. Quietly and emission-free gliding through the waves, even when there’s no wind to power you, is another sailing dream come true.

With 50 full-time and seasonal locations throughout the Caribbean, Bahamas, Indian Ocean, Pacific Ocean, Oceania, Asia, the Americas and Europe, Dream Yacht Worldwide has become a household name in sailing charter vacations. Loïc Bonnet’s vision of offering more boats, more destinations and more choice than anyone else is now a reality, and with its high standard of service, local knowledge and suggested itineraries, Dream Yacht is both an avid sailor’s and a novice’s dream guide to discovering the world’s best destinations.

For more information and booking details, visit dreamyachtcharter.com.

The post Around the World in 50 Destinations appeared first on Cruising World.

Philip Barnard’s family arrived in St. Vincent and the Grenadines more than a century ago, in 1902. His grandfather sailed the local waters. His father then grew up on local boats, and his mother started Barefoot Charters in 1991—an unusual, if not monumental, achievement for a woman in those days. Barnard followed his family’s lead and, today, owns the company known for its well-developed charter base and sailing school.

“We have relationships that go back generations with service providers,” Barnard says. “I know every inch of water down here, taught to me by my dad and granddad before we had GPS. That allows us to show people an experience that’s a little different.”

St. Vincent and the Grenadines is in the southern part of the Caribbean, which is far less developed than the northern charter meccas such as Antigua and Saint-Martin. The experience in this part of the Caribbean is often described as untouched—much like the other, busier islands were decades ago.

Still, there are modern conveniences. The $259 million Argyle International Airport opened just a few years ago on the eastern side of St. Vincent, giving visitors a first-class travel option for accessing the tranquility of the archipelago. American Airlines, Virgin Atlantic, Air Canada and other providers offer service here.

The islands of St. Vincent and the Grenadines run north to south, like an unfastened string of pearls. Conditions are different from other charter hotspots such as the British Virgin Islands, and sometimes include sailing in pure Atlantic Ocean winds.

Barnard describes the locale as ideal for bareboaters who want to step up their sailing game with a bit more of a challenge.

“It’s not like the fishpond sailing in the Virgin Islands,” he says. “Down here, the winds are stronger. This is better-suited for intermediate and advance sailors—and it’s why our sailing school is so good. We can access just about any conditions we want.”

Barefoot Charters offers American Sailing Association and Sail Canada classes that start at beginner level and go up to teaching people how to become instructors. The company also has specialty programs focused on living aboard offshore, preparing for offshore passages and learning how to make decisions in high-stress situations, such as major storms. In some cases, instructors include former participants in the Vendée Globe singlehanded, nonstop round-the-world yacht race.

“These extra courses are for people with bigger aspirations, who want to take the family and go all around the world,” Barnard says. “These techniques make you a better sailor in everyday situations too.”

And Barefoot Charters has a well-established base that not only has a restaurant and rooms for bareboat clients, but that also can handle repairs on everything from sails to fiberglass to diesel engines.

“It’s not a dock with three boats and a guy in a little office,” Barnard says. “We don’t have a chandlery in St. Vincent; although it’s a sailing location, there’s no sail industry, so we have to be self-sufficient.”

Teaching boaters to be self-sufficient is also part of the Barefoot Charters operation. The company offers a program that it calls a mentor charter, where clients are on their own chartered bareboat, fully in command and control, but moving through the islands on itineraries that are like a flotilla, so there is always help nearby if needed.

“It’s for confidence-building the first time out,” Barnard explains. “You can say that you sailed a boat for a week. You got your first 50 miles. That’s the prerequisite a lot of the charter companies have.”

That kind of sailing—and all other types of bareboating—can be done aboard the diverse fleet of boats that Barefoot Charters offers. Unlike other companies that focus primarily on, say, only one type of catamaran, Barefoot Charters offers cats as well as monohulls that are built for different purposes.

Barnard says that the fleet breaks down into two general categories: performance boats and boats that offer luxury comfort at anchor. The idea is that different boats are meant to do different things, so bareboaters should be able to enjoy whichever aspect of cruising appeals to them most. Want to go fast on a broad reach? You’ll need a different type of boat than one packed with amenities for use at anchor. At Barefoot Charters, clients can choose either one.

“Our philosophy is to let the fast boats do what they do, and let the other boats be more comfortable,” Barnard says, adding that some clients come back year after year, chartering different styles of boats to learn what they like best. “I have owners here who learned to sail here, and they’re getting ready to go off cruising now that their kids are graduating.”

Barnard also says that Barefoot Charters takes its obligation to the natural environment seriously. Stewardship of St. Vincent and the Grenadines is a major part of the company’s philosophy, so much so that each charter guest receives a tree to plant while they’re in the archipelago.

“We give a casuarina or flamboyant tree—they’re hardy and can grow here,” Barnard says. “It’s to offset the emissions from the flight down to the islands.”

All in all, Barnard says, the experience that charter guests can have with Barefoot Charters is unlike any other. As just one example, there’s the island of Mustique, which often closes to the public because it’s a favorite haunt of the rich and famous. Here, as with other locations throughout St. Vincent and the Grenadines, clients of Barefoot Charters enjoy special privileges.

“We’ve been able to negotiate access for our clients to Mustique,” Barnard says. “They can go horseback riding, rent a Mule—the golf cart, not the donkeys—and go all around the island. The same is true at Palm Island, which is also exclusive. Our guests can access the hotel grounds and spa with a day pass.

“Because we know so many people around these islands,” he adds, “we have access to a lot of back doors.”

To book a vacation with Barefoot Yachts, visit barefootyachts.com.

The post Local Knowledge, Since 1902 appeared first on Cruising World.

“Aww, c’mon man, don’t let us be that boat!”

I shouted at myself as I cranked the wheel and goosed the throttles, sending the Lagoon 42 Sjevernjaca into a wide, lumbering 360-degree turn. We had to get out of the path of a powered-up race boat that was bearing down on us. 

Standing next to me at the raised helm station was my old sailing mate Dave Robinson. “Oh, that one’s going to be trouble too,” he said three-quarters of the way around the circle, pointing at a sailboat that tacked close to shore and was now headed our way.

I spun the wheel hard again and searched for an open path through the oncoming traffic. The seas were lumpy off the rocky entrance of Antigua’s English Harbour.

It was Day Two of Antigua Sailing Week, which we’d come to watch, not participate in—though now, apparently, we were in the thick of it. Dream Yacht Charters was a sponsor of the event, and when they suggested that I take in a bit of the action and then sail off to see the rest of the island, well, how could I say no? 

We had started two days earlier at the charter base just up the coast in Jolly Harbour. On the last Saturday in April, after provisioning at Epicurean Fine Foods & Pharmacy and then waiting for a leaking faucet to be replaced, we got a late start. Our destination was Falmouth Harbour, home to race headquarters and the first stop on a counterclockwise, weeklong circumnavigation of the island. At the chart briefing that morning, besides a rundown of must-see bays and coves (and a review of the island’s many reefs to avoid), we were told two things: Be on a mooring or anchored an hour ­before sunset, and keep clear of the 85-boat Sailing Week fleet.

With the first advisory top of mind, we motored out the channel in midafternoon, hung a left in open water, and made a beeline for Goats Head Channel, staying inside the reef on the island’s southwestern side. To my surprise—given that this year’s Sailing Week was the first at Antigua after a two-year pandemic hiatus—Falmouth Harbour was not all that crowded. We had no problem picking up one of the Antigua Yacht Club’s guest moorings, relatively close to its dinghy dock. It turns out the bulk of the racers preferred to crowd into adjacent English Harbour, home to Nelson’s Dockyard and a number of marine facilities.

Ashore, we learned that the opening-­night party, to which we’d been invited, had been canceled because of pending weather. The bar was open, though, and the drinks were flowing. Decked out in team colors, sailors clinked bottles and glasses as regattas past were toasted. Outside, several race boats were tied along the docks, their crews offloading gear in preparation for Sunday’s opening race. And on a nearby waterfront stage, the Original Steel Orchestra entertained one and all with a lively assortment of Caribbean tunes.

For dinner, we took a security guard’s advice and walked a short way to the Life on the Corner Bar & Grill, which served up a spicy chicken curry that demanded to be washed down with cold Caribes, followed by a sweet rum punch. The street outside was busy and loud. Back on the boat, we sat forward on the tramp and enjoyed a ringside seat.

Sailing Week, according to its president, Alison Sly-Adams, marks the end of the Caribbean’s regatta season. It started in 1968 as a reason for yachts and crews to stay just a bit longer before heading north, out of hurricane danger or back to Europe. This year’s event was the 53rd regatta, offering racing action to a wide array of sailors. Boats ranged from thoroughbreds such as the Volvo 65 Ambersail 2 and the Volvo 70 Ocean Breeze to mom-and-pop cruisers to a fleet of 29 chartered bareboats. There were 15 classes in all, assigned to two starting areas just to the east and west of the entrance to Falmouth Harbour. 

We joined the eastbound parade of boats Sunday morning to watch a few of the big-boat starts. The action began at 10, with classes taking off at ­five-minute intervals. By the second tack, the front-runners in each heat were lost in the Caribbean haze, so eventually we headed over to the B Fleet’s windward mark and puttered around, watching the spinnaker-­optional cruising and bareboat classes at work. With a broach here, an hourglass chute there and a few collisions with the inflatable buoy, it was all entertaining enough.

The trade winds were forecast to be sporty throughout the week, and they were. After a long morning of bouncing about in the resulting swell, our crew embraced the idea of returning to the mooring to take in a little more of what Falmouth had to offer. We had an invitation to a rum party being put on by Locman, the Italian watchmaker, and then grabbed a $12 cab to Shirley Heights a couple of hours before sunset for the infamous Sunday night jump-up party.

Even on a quite-hazy evening, the view of English and Falmouth harbors from atop Shirley Heights was breathtaking. The place was packed by the time we arrived, and a long line pointed the way to the barbecue pits, where cooks prepared chicken and ribs over wood and charcoal fires. Nearby, craftsmen laid out tables filled with wares. I watched a basket weaver make youngsters happy by fashioning fanciful hats for them out of palm fronds. The bar was busy too, serving libations to a mellow crowd of sailors content to sway to the Caribbean rhythms of the Halcyon Steel Orchestra. 

We watched twilight turn to dark and then headed back down to town, and from there to the boat for a hot dog feast cooked on a charcoal-fueled grill of our own. With the jump-up and Sailing Week visits crossed off the to-do list, we were ready to go exploring.

On the chart, it looked to be about 12 nautical miles to Nonsuch Bay, the first protected must-see anchorage on Antigua’s east coast that was not off-limits to Dream charterers. With just that seemingly short distance to go, we were in no hurry to get started. At the mooring, the breeze felt lighter than it had the day before, but as soon as we were outside and turned east to clear the tip of the island and proceed north, the trades were full-on, gusty and squarely in the no-sail zone of a big cruising cat. Three things became immediately apparent. First, we were in for a long, slow motorboat ride, pounding into ocean swells that made it hard to get boatspeed up to even 5 knots. Second, the A Fleet race committee had designed the day’s distance course to take several classes along the very same coast we needed to traverse. And third, we should have left a whole lot earlier in order to be out of their way.

For the better part of two hours, we played dodge ’em with incoming race boats. In all, it was a wet three-plus-hour slog up what was a textbook lee shore, with water pouring over the cabin top each time a bow buried itself in a wave or a squall rolled through. But still, it was a thrill to see the wildness of the sea, feel the power of the breeze, and take in the lush green hills and rocky outcrops that marked this part of Antigua. I’d do it again in a heartbeat, though perhaps not in the midst of a regatta.

Soon enough, we spotted a white structure on a headland that the cruising guide said looked like a lighthouse. Just past it lay the pass into Nonsuch Bay—a slice of deep water through outcroppings of rock and coral jutting out between the mainland and Green Island. As we turned and ran west, surfing down the ­wind-driven swells, the early-afternoon sun was high overhead, making it easy to spot the shallow spots. Closer to shore, the waves laid down, and once inside, though a gusty wind still blew, the water was calm. Relief!

Nonsuch Bay is a truly lovely place—my favorite spot of the week, I think. Inside, to the east and south, the hills are tall, with a few homes and resorts tumbling down to the water. Just past the entrance, there’s Middle Reef to skirt, with good water to either side. To the right, there were a couple of boats anchored off the northeast end of Green Island, and farther along, a handful more tucked in behind the reef.

We broke left and motored deep into the bay to what, on the chart, appeared to be a well-protected spot surrounded by mangroves in Ayres Creek. We dropped anchor in about 12 feet of water just off a resort dock, and then watched a cloud of mud billow up as we backed down and plowed the hook along the bottom.

Plan B? Head back to Green Island and anchor in sand. Besides way better holding, we found great entertainment, thanks to 40knots—a local watersports school that offers kite-, wing- and paddleboard lessons off the beach and from a sailboat anchored by the reef. We witnessed a variety of skills. There were soaring leaps and landings, as well as the occasional chase-boat rescue of a newbie blown astray. As for our crew, we grabbed masks and snorkels to sit on the beach at Green Island. Underwater, there wasn’t much to see, save for one enormous hermit crab. It was a good swim, though, on a hot afternoon.

Sunset that night was the best. The sun dipped below the hills to the south, and the water inside the reef was calm, the breeze steady. If cruising, this bay would be a place you might stay for days or weeks. Unfortunately, we were on rented time and had places to go.

Tuesday got off to another wet and bumpy start. We followed our track back out the pass, planning to motor upwind until we were clear of Green Island and could set sail for Horse Shoe Reef Channel and the entrance to Parham Sound at the north end of the island.

As we retraced our steps, the waves built as quickly as they’d subsided the day before. One roller caught me off guard, and rather than bearing off to take it on the forward quarter, Sjevernjaca plowed square in, burying both bows with a shudder. Stepping below, one of our crew discovered water in the hallway outside his forward cabin; inside it was more like an aquarium. A hull hatch had been left open. As if to prove a point about the power of hydrodynamics, the sea had sent remarkable amounts of water pouring in, soaking everything in its path.

At last in deeper water, the seas mellowed. We hauled up the main, cracked off, and rolled out the self-tending jib. Sailing, at last! It was a good 5-mile reach that began with breeze on the beam and ended up with us nearly on a run. 

The coast along this part of the island is low-lying, making it tricky to pick out landmarks. We searched for Prickly Pear—a sandy islet just offshore that serves as a range mark through Horse Shoe Reef Channel. Once we spotted it and made our turn, even with the aid of the chart plotter, the shallows to either side of the channel were hard to spot until we were nearly on top of them, but we made it through and followed the charted route south through reefs to the sandy beach at undeveloped Maiden Island. It turned out to be a good spot to swim and kick back. With the VC Bird International Airport across the way and boat traffic passing by, there was plenty to watch. Toward sunset, two cruising sailboats pulled in, but otherwise we had the place to ourselves.

In the morning, we set sail and picked our way back along the shore, passing inside Prickly Pear, bound for Boon Channel. The route kept us well off the reefs to the north. In daylight, with a chart plotter, this was an easy passage, but looking at the Imray Iolaire chart on board, I once again had a great appreciation for Don Street plying and charting these waters with a compass and lead line as he mapped and wrote his cruising guides aboard the engineless yawl Iolaire.

Our journey that day—and for the rest of the trip, for that matter—delivered a nice, but brief, sail. The distance from Maiden to Dickenson Bay is just 7.5 miles, and we flew along with the still-gusty trade winds behind us. Dickenson is home to Sandals and a couple of other all-inclusive resorts that dominate the long, crescent beach, but we found an open stretch at the south end and anchored there late morning in about 9 feet of water, near a thatched-roof raft known as the Kon Tiki Bar. 

After lunch and a swim, three of us were eager to go ashore and stretch our legs. With no good place to land or leave a dinghy, one of our crew dropped us at the beach, where we followed a rutted dirt road to a paved one. Resorts lined one side of the street; on the other, we strolled past a large pond and an abandoned miniature golf course, complete with a faded cruising catamaran that doubled as a hazard. A local pointed us in the direction of a small convenience store, saving us a long walk or cab ride to a market to replenish our dwindling stock of beer and chips. 

Later that afternoon, we visited the tiki bar—our first watering hole since Falmouth that wasn’t all-inclusive and that was open to non-guests. It was a lively place, and “Johnny from Denmark” ruled the bar. He was quick to serve us a cold Caribe when we stepped aboard from the inflatable.

Johnny had a tale to tell. He’d come to the island for a two-week visit 22 years earlier and, well, fell in love with the place. He managed a restaurant on the beach for several years but lost it when the owner died and it changed hands. Four years ago, he made good on a dream to build and open the Kon Tiki Bar along with his better half. The pandemic was a setback, and, added to that, he and his partner split up, he said. Now he gets the raft for a week, then takes his liquor home, and she brings her own booze for the next. “That’s just the way it goes,” he said with a shrug. “I’m working one week, then I have a week’s vacation.”

An assistant sat off to the side of the bar and manned a runabout to ferry visitors back and forth to shore if they didn’t want to make the short swim. As the day went on, the number of visitors grew and the music got louder. By the time we left, it was packed with a raucous crowd awaiting sunset.

Thursday was our last full day aboard Sjevernjaca, and as the crow flies, we didn’t have far to go to skirt the entrance to St. John’s Harbour and arrive at our next destination, Deep Bay. The breeze was still honking from the northeast and we were in no hurry, so we hoisted sail and struck out on a long reach out to sea and back, getting in a couple of hours of good sailing before dropping the hook.

Deep Bay was yet another lovely destination. As we motored in, we had no trouble spotting and avoiding the wreck of the Andes, a barque that had caught fire and sunk while carrying pitch to Chile in the early 1900s. Inside, we anchored in about 9 feet of water. 

The Royalton Antigua resort takes up the southern end of the beach, and a few small shops dot the shore, but most of the strand is backed by lush green shrubs that hide a salt pond behind. Ashore, we scrambled up the steep path to Fort Barrington, built by the British in 1779 on the headland overlooking the approach to St. John’s. The view was spectacular. We could just spy Montserrat through the afternoon haze, and we got a panoramic view of Antigua’s mountainous interior. 

Friday, we managed to create another extended sail for ourselves by reaching out past Sandy Island and its off-lying reef, and circling back to visit pretty Hermitage Bay and Five Islands Harbour, where the Shekerley Mountains tower over the anchorages. We stopped for lunch and a swim, and lingered as long as we could before motoring out and around the point, back to Jolly Harbour and the charter base. It had been a fine week with plenty of breeze for sailing, a happy crew, and sights to see. 

Saturday morning, as we cleaned the boat and packed, I spotted the crew from Talitha on the dock. I’d met them at the start of the week, when they were getting their rented Beneteau Oceanis 41.1 prepped for action. Skipper Jeff Dickinson along with the rest of the crew of eight all hailed from Aspen, Colorado, and are members of the Aspen Yacht Club. It was his third Caribbean regatta, he’d said. And of course, they expected to win their bareboat cruising class. 

“I love Antigua,” he told me. The pace of the regatta is just right: two to three hours of racing, then a party, plus a lay day for scuba diving.

So how did they fare? 

Well, they had fun. Dickinson was back at a rented condo where half of the crew had stayed at night. But his mates who returned the boat reported that Talitha was first over the line in three races—a victory of sorts—though they ended fifth overall on corrected time. One thing they were certain about: They’re coming back to race again. “Absolutely.”

Mark Pillsbury is a CW editor-at-large.

Charter Racing

Antigua Sailing Week is one of several Caribbean regattas that include a charter-­boat division. For this particular week of racing, Aspen, Colorado, skipper Jeff Dickinson said that charterers can’t request a particular boat and can’t campaign the same boat two years in a row. § Erin Minner, Dream Yacht Charter’s sales manager for the Americas, says that racers have a few other requirements to consider. The minimum charter time is 10 days. There is a race-pack charge that includes a more detailed boat briefing and a check to ensure that sails are in good shape. The base registers the boat with race officials. There is a regatta surcharge of approximately $2,000, depending on the boat and event, and the security deposit is doubled. Dream Yacht Charter lets its boats participate in Antigua Sailing Week, the Caribbean 600 and the BVI Spring Regatta. § If you’re planning to escape winter and go racing, check with the regatta and local charter bases for yacht availability.

The post Charter Holiday at Antigua Race Week appeared first on Cruising World.

Two fleets departed the US East Coast this past fall, bound for the Caribbean as part of annual rallies to the islands. The North American Rally to the Caribbean, a 1,500-mile offshore voyage from Newport, R.I., to Saint-Martin via Bermuda, was “a piece of cake,” as one sailor put it. But the other, the 2022 Salty Dawg Sailing Association Rally, well, that’s a different story.

The 22nd annual NARC departed Rhode Island on October 30 with 19 boats that arrived in Bermuda without incident less than four days later. Another five boats, part of the Salty Dawg Sailing Association Rally that historically leaves from the Chesapeake area, signed on to join the Bermuda-bound NARC fleet—but two of those boats turned back before reaching the Gulf Stream, and two never got out of Newport.

Hank Schmitt, who has been organizing the Newport-based NARC for 22 years, arrived in Bermuda on his Swan 48 Avocation in three days, 22 hours. He said the boat rode the Gulf Stream for 30 hours and pushed along at 2-plus knots, knocking half a day off a four-day trip.

Steve Burlack, owner of the J/46 Arrowhead, also reported no issues. “Fun trip,” he said. “Pretty much the same as the other four times I’ve sailed [to Bermuda]. The Gulf Stream presented no major issue. One rough night with squalls, thunder and lightning, with winds 30-plus knots. A good reaching breeze filled in after that, and we were flying the rest of the way. [We sailed] mostly one reef in the main and flew a No. 4 on inner forestay. Then rolled out the 104 percent the last day. We were in good company with the NARC boats the entire trip. Four of us came in pretty much together.”

Around the same time the NARC departed Newport, four sailboats left the Chesapeake to join the NARC in Bermuda. Three boats arrived in St. George’s without incident, and one turned back. Solana V, Endeavor 2 and Cameo made the crossing in less than four days.

“The first night in the Gulf Stream was rough, with winds from north,” reported Douglas Hauck, aboard Cameo, a 48-foot Leopard. “One of the mainsheets broke in the middle of the night, but we were able to keep the main up. Fixed the following morning. Day three, nice sailing, but the night was very rough. Confused seas. We took the main down during the night when it got squally and motorsailed the rest of the way with full jib. We hit a 40-knot squall a few hours before entering the harbor. No issues entering the harbor in the dark with north-northeast winds.”

After a few days of parties, rest and provisioning, on November 8, half the NARC fleet departed Bermuda for the 875-mile sail to Saint-Martin. The rest of the fleet left five days later.

On November 13, Schmitt on Avocation arrived in Saint-Martin. “Pretty easy passage down from Bermuda,” Schmitt said. “More rain than normal first two days, then motored for a day, then nice sailing in the trades the last day.”

All in all, this year’s NARC Rally went off without any serious incident—but the Salty Dawg Sailing Association’s Rally to the Caribbean was not so lucky. The rally had amassed more than 120 yachts in marinas and anchorages near the mouth of Chesapeake—the largest flotilla in the Salty Dawg’s 11-year history. Most boats expected to depart November 1 for the nonstop, 1,500-mile sail to Antigua. Another 30 boats were planning to depart the same day, but were bound for the Bahamas. 

The start was postponed when a disturbance in the middle of the Bermuda Triangle had forecaster Chris Parker, from Marine Weather Center, worried. He couldn’t see a weather window opening any time soon. Parker suggested that the boats planning to sail to the Bahamas could depart November 1, provided they aimed to arrive before Friday’s increased easterly winds, and tried to stay west of the ridge. That ridge eventually turned into a subtropical storm and Hurricane Nicole.

Around 30 boats elected to head for the Bahamas, leaving the Chesapeake on October 30 and 31. They sailed around Cape Hatteras and headed south, inside the Gulf Stream, turned east to cross the stream near 34 north, and then headed south again for the Bahamas. Another seven boats elected to creep along the coast or down the Intracoastal Waterway. A few dropped out of the rally. The remaining 60 boats stayed in Hampton, Virginia, waiting for better conditions. They waited nearly two weeks.

As it turned out, subtropical storm Nicole turned west, heading for the Abacos, where the 30 Salty Dawgers were hunkering down. Mark Hill, on the Tayana 48 Oasis, was docked at the Abaco Beach Club marina in Marsh Harbour when the storm arrived. “It was a wet and wild night, and wild all the next day,” he said. “It blew 50 knots for hours with gusts to 70.” After blowing over the Abacos, Nicole became a Category 1 hurricane, and one day later slammed into Florida’s East Coast.

Despite all the predictions and warnings, two of the Salty Dawg yachts left the Chesapeake on October 31, and somehow made it all the way, nonstop, to the Caribbean in less than 10 days.

“We had no plans to stop in the Bahamas,” Mark Kerestres reported after his Catana 46 Inio arrived in Puerto Rico, nine days out of the Chesapeake. “We planned to just keep going as far south and as far east as we could. The islands were there if we needed to stop. We kept west of the ridge that developed into the tropical storm, steering south. We threaded our way through the lower Bahamas at 10 knots in a south-southeast wind, 20 to 25, with higher gusts in squalls.”

The catamaran Vanamo, a Lagoon 400, also elected to bypass the Abacos and kept sailing south. They picked a more eastern leg but did stop for fuel at Cockburn Harbour in the Turks and Caicos, and, later, in St. Thomas, arriving in Saint-Martin on November 12—the same day the remaining 60 Salty Dawg boats left the Chesapeake.

Parker had advised the Salty Dawg fleet that there was an option for going south, outside the Bahamas to the Turks and Caicos and then east along Hispaniola and Puerto Rico, motorsailing. The disturbance that turned into Nicole had suppressed the trades and sent the winds north around the developing low. This allowed for a westerly wind to affect the area north of the Greater Antilles, giving the two Salty Dawg catamarans a way to make it all the way down. 

Parker advised the remaining fleet on an area of potentially reinforced trades affecting the fleet as they turned south, but it never developed, and the 50 or so boats that left the Chesapeake on November 12 had a delightful trade-winds romp all the way to Antigua. There were a few problems reported, but nothing serious; one boat lost its rudder, but managed to return to port, while another lost its engine and was towed back to port. 

More than a hundred boats in this year’s Salty Dawg Rally made it safely to their destination, one way or another.

The post A Tale of Two Rallies: Sailing Fleets Head South for the Season appeared first on Cruising World.

There’s no greater vacation joy than letting mood set the course for the day—and no destination offers a better mix of well-stocked beach bars with lively crowds, quiet coves to escape to, white-sand beaches and watersports galore that cater to all your moods than the British Virgin Islands.

This Caribbean destination has long been a haven for boaters, thanks in part to the massive fleet available for rent out of Tortola, the main island, as well as the welcoming waters where those with less ocean experience quickly build confidence—and those with ample experience find new challenges and pleasures while taking on the Sir Francis Drake Channel and beyond.

Just a 2-minute drive from the Terrance B. Lettsome International Airport on Beef Island, is Tortola, home to the bigger grocery stores and outfitters to jump-start any trip. It’s a destination worth exploring all on its own, especially by boat, because its coves and bays are both unique pockets of color and character. Soper’s Hole, a popular anchorage, is home to a lineup of pastel homes with picturesque white-gingerbread trim, as well as the iconic favorite, Pusser’s West End, a restaurant and bar with burgers, rum drinks and the chance to stock up on boating attire. Cane Garden Bay is another favorite of boaters, including Jimmy Buffett, for its protected anchorage and the chance to eat just-caught seafood on the beach at Myett’s Garden Inn. Quito’s Gazebo, also in Cane Garden Bay, is a locally owned hotel, bar and restaurant known for the reggae bands that jam out just yards from the turquoise water. You can easily eat your way around Tortola, but you’ll also want to stretch your legs and explore, especially taking on the hike up to Sage Mountain National Park, the highest point in the BVI and a great photo opportunity. 

From Tortola, the majority of islands are strung like beads on a curved necklace, all sitting across the Sir Francis Drake Channel. Of that chain, Virgin Gorda is the northernmost, surrounded by a peppering of satellite islands, including Richard Branson’s Necker Island and the Dog Islands, famous for snorkeling. The must-see spot on Virgin Gorda is The Baths National Park, an impressive collection of basalt boulders nestled together to create grottoes and tunnels that you can explore and climb through. Multiple routes weave throughout, each leading to a different high point perfect for taking a group photo or a hand-holding group high jump into the deep waters. For a relaxed meal or cocktail while taking in this epic scenery, head to the Top of the Baths and tuck into a grilled lobster before enjoying a frozen coffee drink or mudslide cocktail poolside.

From Virgin Gorda, it’s a two-and-a-half-hour sail to Anegada, an 11-mile island that is easily the least visited of the inhabited BVI, making it a rare gem well worth the effort. The outdoor experiences here deliver that something extra, such as from Cow Wreck Beach, a haven for solitude-seekers who can walk miles in both directions, sometimes without encountering another beachgoer. Of course, you will find fellow boaters and island-lovers at the Cow Wreck Beach Bar, an open-air hangout with a timeless Caribbean vibe. Anegada also attracts divers and snorkelers looking to explore Horseshoe Reef, the Eastern Caribbean’s third-largest continuous reef, home to eagle rays, Atlantic spadefish, permit and a host of other wildlife.

This outpost island is a big destination come November, when the Anegada Lobster Festival kicks off. Held the weekend of American Thanksgiving, November 25-27, it brings together unique outdoor activities, such as an islandwide scavenger hunt and culinary celebrations centered on this Caribbean bounty.

The island of Jost Van Dyke, found off the back side of Tortola, is one of the BVI’s best day trips, home to a handful of beach bars where the Painkiller cocktails keep flowing as day-trippers enjoy the music and the shallow waters that make for a super-relaxing day. Soggy Dollar Bar anchors the scene and is said to be the originator of the Painkliller, the island’s famous cocktail: a mix of premium dark rum, cream of coconut, pineapple and orange juice (proportions are secret), and topped with freshly grated nutmeg. Beyond the bar scene, Jost offers hiking trails and scuba diving on the dynamic reefs of its Atlantic coast. There’s also paradise found in the form of Sandy Cay, an uninhabited spit of island with a bit of palm forest and the softest sand imaginable, perfect for throwing a football, playing frisbee or simply enjoying the view. Jost offers three overnight anchorages, so plan ahead to enjoy a full day and make a night of it.

Plus, so much of the beauty of the BVI lies in between. On and throughout the main islands, you’ll find more than 17 anchorages, including a few surprises that take you off the beaten path. Take Salt Island. It’s a popular day trip for scuba divers ready to witness the R.M.S. Rhone, arguably the Caribbean’s most storied and best-preserved shipwreck, dating back to 1867. Boaters have the unique pleasure of catching the sunrise and a snorkel or dive before the scuba day-trippers arrive. Salt Island also offers a hiking trail that shimmies up to a few cliffs overlooking crashing waves. Or anchor at Norman Island, another uninhabited island with a restaurant for day trippers, that offers hiking trails and caves to explore.

Spend your days sailing, snorkeling, scuba diving, walking the beach, rating the cocktails at the beach bars, hiking, and exploring—it’s all in the mix here in the British Virgin Islands.

For more information on the BVI and to start planning your next getaway, visit their website.

The post Cruise the British Virgin Islands appeared first on Cruising World.

There is nothing quite like a sailing vacation. Whether you’re after sunshine and beam reaches, rum drinks and reggae, or quiet anchorages and adventures ashore, a charter with The Moorings can have it all. Now that the world is opening back up, it’s time to ditch the staycation and choose a destination. Let’s take a look at where the hottest destinations are for 2022 and 2023, what’s changed in the world of charter sailing, and what you need to know before your next vacation.

Back to the Bahamas, BVI and USVI

Long the most popular destinations for North American sailors, bases in the Virgin Islands and the Bahamas have had major setbacks from hurricanes and the pandemic. Fortunately, those days are mostly in our wake, and charter sailors can once again easily cruise the storied waters of the Sir Francis Drake Channel, the Sea of Abaco and the Bahama Banks. 

The Moorings base is fully open in Road Town, British Virgin Islands, at Wickhams Cay II, where you will find resort-like amenities to enjoy before casting off. Travelers no longer need to preregister at the travel portal for entry clearance and all Covid entry testing requirements have been lifted as of July 15, 2022. Once aboard your boat, the rest of the BVI is yours to discover—explore the magical Baths on Virgin Gorda, sip a Painkiller at the Soggy Dollar on Jost Van Dyke, and check out the Indians, one of the best snorkeling spots in the area.During the pandemic, the US Virgin Islands surged in popularity as a charter destination due to ease of travel for US residents. Once a well-kept secret, the allure of these islands is now getting the attention it deserves. From The Moorings base at the Marina at Yacht Haven Grande, you can explore all that St. Thomas offers, including abundant shopping and nightlife, then head out to explore beautiful and laid-back St. John, where you can experience the pristine beaches of Cinnamon Bay, excellent snorkeling at Leinster Bay, and even some hiking trails at Virgin Islands National Park.

The Moorings base at the Abaco Beach Resort in Marsh Harbour, Bahamas, reopened at the end of 2021 after recovering from the devastation wrought by Hurricane Dorian in 2019. “While the impact of the storm can still be seen on the main island,” says Ian Pedersen, senior marketing manager for The Moorings, “the cruising ground and outer cays have returned to form and are a spectacular sailing destination once again.” The central location of Marsh Harbour makes it the perfect place to start your exploration of the Abacos—a longtime favorite destination for cruising sailors. Enjoy sailing in the protected waters of the Sea of Abaco to destinations that include quaint villages, such as Hope Town and Green Turtle Cay, and abundant secluded anchorages.

If you’re looking for an Out Islands experience, an Exumas charter might be for you. Departing from The Moorings base at Palm Cay Marina in Nassau, Bahamas, visitors can then cruise down to the Exuma Cays, a string of 365 islands and cays that stretch for 120 miles. Many sailors who have traveled the world agree that the Exumas are their favorite cruising ground. Once you go, you will understand. From exploring the mangrove creeks of Shroud Cay and the incredible Thunderball Grotto, to the friendly settlement of Black Point and colorful Staniel Cay, the Exumas offer a wide variety of experiences—and unforgettable sunsets on the Great Bahama Bank.

Both Bahamas destinations are fully open to vaccinated travelers, while unvaccinated visitors will need to show a negative COVID-19 test at check-in.

The Magical Med

If your dream sailing vacation includes exploring ancient ruins, villages steeped in history, and a variety of sailing conditions, a sailing vacation in the Mediterranean might be just what you’re looking for. “After so many people were unable to sail in Europe during [the pandemic], the Med sailing season is back and as popular as ever,” Pedersen says.

From The Moorings bases in Italy, Greece and Croatia, visitors can choose the Med experience that suits them best. Looking for sun-soaked beaches, quaint tavernas and excellent scuba diving? Try a charter from Corfu in Greece. Does visiting an abundance of islands offering everything from wild, barren landscapes to historic towns and lively nightlife sound ideal? A Croatia and Dalmatian Islands charter is for you. How about a view of mountain peaks, incredible cuisine and soaking in hot springs? Check out a sailing vacation from Sicily.

Whichever you choose, a charter in the Med is an incredible experience. If you are looking to do a bareboat charter in one of these destinations, you will need to have an approved sailing license, such as an International Proficiency Certificate, or have passed ASA 104 (Bareboat Cruising) or US Sailing Bareboat Cruising courses. No certifications? No worries. Crewed charters are available with a captain and a chef.

Ready to Go?

After two-plus years of various lockdowns and travel restrictions around the world, it’s no surprise that stir-crazy sailors are ready to get out there. If you’re considering a charter vacation in the near future, The Moorings strongly suggests booking as soon as possible to ensure you can get the yacht you want. “We are already seeing strong bookings for next summer and even fall of 2023,” Pedersen says.

So, gather up your crew, choose your destination and go sailing.

For more information and to start booking your charter vacation, visit www.moorings.com or speak to a vacation planner directly by calling 800-416-0247.

The post Back to Chartering (and Better than Ever) with The Moorings appeared first on Cruising World.

As I made my way toward the stage, stepping carefully through the children seated cross-legged on the floor, a familiar tune rang out in the tropical night. A tall guitarist and his sister led the crowd in a cruiser’s version of perennial favorite “The Lion Sleeps Tonight.”  

Daily plotting the fleet positions, we read the new forecast. 

Carefully checking all the veg to see what did not last. 

Joining in were faces now familiar to me: a British woman with a ukulele, a father-­daughter duo on violins, a young American man on a tiny electric travel guitar. Less than a week earlier, these sailors had been strangers. Now, on the final night of the weeklong festivities and ARC Plus welcome events, I sang along with the families and crews who had made the journey across the Atlantic. 

The World Cruising Club’s Atlantic Rally for Cruisers began in 1986 as a way for sailors, especially amateurs, to participate in a race across the Atlantic. The ARC emphasizes camaraderie and safety within the fleet for the 3,000-nautical-mile passage from the Canary Islands to St. Lucia. The ARC Plus route was added in 2013 to meet growing demand, as well as to give participants the option of breaking the journey into two legs. The ARC Plus route ­traditionally takes the fleet from the Canary Islands to Cape Verde, followed by the 2,000-nautical-mile passage to St. Lucia. This year, the ARC Plus saw 70 boats with crew from 26 countries depart Gran Canaria and sail south “until the butter melts.” After a short stopover in Cape Verde, the fleet set their sights on Grenada for the first time. Moving the ARC Plus fleet to Port Louis Marina in St. George’s eliminated the pressure on the ARC Plus participants to move on from St. Lucia to make space for the direct ARC arrivals.

A few days before the first boat arrived in St. George’s, I reached out to Sally Eardle, a family friend and the owner and editor of the Caribbean Compass, a local sailing newspaper. Sally is a veteran of the ARC arrivals, and I asked her if she thought I’d be able to jump into the festivities. She assured me that the fleet is known for an infectious positivity. “People are usually happy to speak about their experience.” I learned quickly that she was right.

During my first morning on the docks, I met Dale and Megan Simonson, on Helios, an American father-daughter duo from Illinois who were new to sailing and crossed the Atlantic on their Lagoon 52 with three other crew. Megan, 18, is a recent high school graduate on a gap year, and was the catalyst for this adventure. “We wouldn’t be here if it weren’t for her,” Dale told me. “She gave me the courage to retire and buy the boat.”

Dale and Megan introduced me to Traci and Andrew Roantree on the British-flagged Beneteau Oceanis 45 Walkabout, but our conversation was cut short. “I need to get to ukulele practice,” Andrew said. I was intrigued. He told me that a member of the fleet had written a song about the ARC Plus, and a few sailors had bought ukuleles in Cape Verde with the intention of learning the music during the passage, but of course most of them didn’t; they were ­headed for a last-minute practice.

I continued on my way, only to come across another ukulele student. “My husband is the mastermind behind the song,” Lori Green told me as she pointed to a tall, slender man with a guitar case on his back. “It’s just a fun little thing I do for the rallies back home,” Barney Green said. The Greens have been living aboard their Bavaria 51, Favorita of Hamble, since June 2020. They had originally planned to do the ARC Plus in 2020, but like so many others, decided to postpone their cruise due to COVID. “Anyway, we’re here now,” Lori said with gratitude and relief. Barney told me that he began writing songs when he was the commodore at the Newbury Yacht Club, just outside London. The yacht club is “famous for being possibly the farthest yacht club from the sea,” he said.

I hung around to see who else was part of this merry little band of sailors, and ran into Paul Youngblood, whom I had met the previous day aboard his uncle’s Ted Hood 52, High Cotton. Paul, a 24-year-old from Minneapolis, is first mate on board and is on the last leg of an Atlantic circumnavigation with his uncle, John. Having crossed from Newport, Rhode Island, to the Azores in June 2021, they plan to take their time cruising the Caribbean, with Paul staying on board while John flies in and out from his work in financial services in New York. They did the crossing with two other crew on board, but it wasn’t without its challenges—namely, the misprovisioning of coffee and the necessary rationing that ensued. “Two and a half cups of caffeinated and one and a half of decaf per person, per day,” Paul had written on their blog shortly after departing Cape Verde. This misfortune was compounded by the fact that their autopilot stopped functioning during the first leg, forcing the crew to hand-steer for the duration of the Atlantic crossing, though they didn’t seem phased. “I’d say we’re all much better at the helm now than we were before,” John said with a laugh. 

The High Cotton crew’s modest versatility was a common trait among the ARC Plus participants and planning committee. I got the chance to talk with Trish Jenkins, one of World Cruising Club’s famous Yellow Shirt team members. The Yellow Shirts are the boots on the ground who make sure events go off without a hitch and provide unwavering support to the participants. “We really didn’t know what events we’d be able to do this year, but we’ve worked closely with all the officials here [in Grenada], and it’s just fantastic to still be doing the ARC Plus,” Trish told me.  

Among the most flexible and resilient participants are perhaps those on the family sailboats, many with young children aboard. Christian and Julie Pukelsheim on the Contest 42 Lady Blue had been planning for five years to cross the Atlantic with their three kids, now ages 11, 8 and 4. Unfortunately, when sudden and severe seasickness struck all but one of the children during their four-month voyage from Northern Spain, they were forced to rethink their plans. In the end, Julie and the kids flew across while Christian, who dreamed of having a family Christmas under a coconut tree in the Caribbean, found some last-minute crew to sail with him. As for their plans now? “We’ve been planning this for five years, and the plan ends today,” Christian said of his German family. “It’s a totally new feeling to not have a plan.”

I got a similar response from Australians Tillman and Verena Coxhead on board their Dick Zaal Skimmer 39, Big Bubble. “We made plans to come here, but we never thought we’d actually make it,” they told me. Their youngest of two children, Caruso, celebrated his 2nd birthday in the middle of the Atlantic and was one of the youngest in the fleet this year. When I asked them if they had any concerns about crossing the Atlantic with such young children, they assured me that they didn’t. “Any family boat who thinks about doing something like this, I would encourage them to; it’s a once-in-a-lifetime experience,” Verena said.

The same sentiment was echoed by most of the ARC Plus sailors. Maybe it was the fact that so many had postponed the adventure for a year due to COVID, or the uncertainty of last-minute changes and unexpected challenges, but everyone seemed incredibly grateful and relieved to finally be in Grenada. After the final evening of award presentations and celebrations, as Sally and I made our way back to the marina, the last verse of the ARC’s unofficial song played in my head:

Finally landing in Grenada, we smell, we’re tired, and it hurts. 

Hoping rum punch will make things better, we search for yellow shirts. 

I asked Sally how this year’s ARC Plus event compared with ones in the past. “You know,” she told me, “every ARC is different, but I think this one really had something special.” 

I couldn’t agree more.

Lexi Fisher is a Grenadian/Canadian writer, freediver, and co-author of The Cruising Guides to the Windward and Leeward Islands.

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