Few people would dare claim that anyplace other than the British Virgin Islands is the world’s mecca for bareboat charters. The BVI’s line-of-sight sailing, reliably beautiful weather and abundance of charter-ready boats make the waters around Tortola, Virgin Gorda and Jost Van Dyke a paradise for skippers of all levels. But sometimes, there’s an itch to push a little farther. Seasoned bareboat skippers often look well past the last mooring buoy and wonder if they have what it takes to harness the winds and waves in more challenging locales. Here’s where the experts say those adventurous skippers should book a bareboat charter next.

ST. VINCENT & THE GRENADINES

The waters around these islands of the southern Caribbean can be so challenging, Horizon Yacht Charters prohibits its bareboat clients from visiting some of them.

“We actually have some places on our contract where you’re not ever to go,” says reservations specialist Lesley Dowden. “They tend to be quite deep anchorages with a lot of currents, so you might be dug in nice, but the current changes and it whips the anchor away.”

The company’s bareboat contract also specifies no sailing on the east coast—the open-Atlantic side—of any islands in St. Vincent and the Grenadines, and it prohibits using the southern entrance to the Tobago Cays, Dowden says. “We’ve had a few people ignore those instructions, and they end up grounding the yacht,” she adds. “There are reefs.”

At the same time, though, sticking with the more manageable spots in St. Vincent and the Grenadines can offer a real thrill for bareboaters used to less-challenging destinations, says Ian Pedersen, senior marketing manager for The Moorings. “The Windwards offer all the staples of a Caribbean adventure but on a grand scale, from the exotic peaks of St. Lucia, long passages to St. Vincent and the myriad unspoiled islands through the Grenadines and Tobago Cays,” he says. “It is a vast and diverse cruising ground unlike anywhere else in the world.”

FRENCH POLYNESIA

Pedersen also urges adventurous bareboaters to head to the South Pacific and book a week or two in French Polynesia. Tahiti is the most popular of these islands, and it’s easy to access with international flights. It’s part of an archipelago that includes Raiatea, Taha’a, Huahine and Bora Bora.

These islands have majestic, towering backdrops that grew out of volcanic activity. The lush, green landscape is a stark contrast to the expansive, white-sand beaches, along with the crystal-clear waters that allow snorkelers and divers to check out everything from Volkswagen-size coral heads to multiple species of sharks. Each year between July and November, humpback whales migrate here to join the fun.

Locals on lesser-known islands such as Raiatea, Taha’a and Huahine are accustomed to bareboaters visiting, and will often offer services that range from beach barbecues to lessons in traditional canoeing techniques. The islands all have flavors of their own.

“Each offers its own majestic experiences, both above and below the water,” Pedersen says. “Some longer crossings are required to get from island to island, making this the perfect spot for those looking for a bit more of a navigational challenge, but with an incomparable reward.”

BELIZE

In Central America, Pedersen recommends Belize as a destination for bareboaters with The Moorings who want a bit more of a challenge. It’s home to the second-largest barrier reef system in the world, after Australia’s Great Barrier Reef, and is the kind of destination where encounters with nature take center stage above and below the water.

On land, just a few of the animals that call Belize home include jaguars, cougars, howler monkeys, toucans and crocodiles. Underwater, the wildlife ranges from bottlenose dolphins and sea turtles to more than 500 species of fish, all making their homes amid about 100 species of coral. Few regions in the world can even come close to that kind of biodiversity, let alone in a location where bareboat charters are available. “Navigation skills are key, however, as the reef system and shallow waters certainly present their own challenges,” Pedersen says. “But the remote nature of this cruising ground offers a chance to escape from the hustle and bustle of everyday life, or even to escape from some of the busier, more popular charter destinations, providing the opportunity to really slip into island time.”

GREECE

The siren song of the Greek Islands has called out to the hearts of sailors for centuries. The Aegean archipelago, the Cyclades, the Dodecanese—each set of islands in Greece’s waters has its own colorful towns to meander, archaeological ruins to explore, and natural scenery to enjoy. All kinds of boats ply these waters that are literally the stuff of legend, whether by foraging with nets off the stern or by relaxing with hammocks out on deck.

But Mother Nature is just as present as any of the Greek gods in this place, and she routinely asserts herself with the Meltemi winds. They are a dry, northeasterly type of wind that usually arrives in the summers, and that can build from 10 to 15 knots in the mornings up to the high-20-knot range in the afternoons. That’s a 5 or 6 on the Beaufort scale, the levels just before “near gale” and “gale.” It means moderate to large waves, whitecaps and spray, and rigging that starts to moan instead of whistle.

At the same time, skippers can set course in a way that Dream Yacht Worldwide describes as exhilarating.

“There are ways to manage these winds and enjoy some spectacular sailing in Greece,” according to the company. “It can make a well-handled sailingboat fly like an arrow.”

Bareboaters thinking about trying to tame this beast in Greece should book with a company that’s prepared to offer charts, itinerary suggestions and backup from skippers with substantial local knowledge. Sunsail has several bases in Greece—in Corfu, Lefkas and Athens—and offers flotilla and skippered charter options in addition to go-it-alone bareboating. The flotillas cruise through the Aegean and Ionian archipelagos, giving participants a chance to go ashore on numerous islands along the way. The skippered charters, as Sunsail says, are a way to “improve your sailing skills in safety and enjoy a relaxed approach to coastal cruising.”

ANEGADA

For bareboat skippers who simply cannot bear the thought of breaking away from their beloved British Virgin Islands, there is an option to take the cruising challenge there up a notch: a crossing to the island of Anegada.

Anegada is not on the itineraries of most bareboaters in the BVI. It’s about 11 miles from Virgin Gorda, and it’s ringed by submerged coral heads that lurk like mines planted to wreck every hull that approaches. More than 200 known shipwrecks have found their watery graves here throughout the years.

But for skippers who want to trade their Painkillers for a splash of adventure, Anegada offers the reward of less-crowded, sandy-white beaches along with memorable snorkeling right off the sand. And, with the sun directly overhead to help spot the coral below—say, an 8:30 a.m. departure from Virgin Gorda’s North Sound and an arrival at Anegada by midday—it’s possible to reach the mooring field off the Anegada Reef Hotel safely, soundly and with plenty of time to spare before a lobster bake for dinner.

Some bareboat companies forbid any attempts to visit Anegada, while others require a check-in the morning of departure, to be sure the winds are less than 20 knots with seas under 8 feet. Seasoned skippers can discuss options with their favorite bareboat companies to determine whether their own experience level is a good fit for this passage in the BVI. 

This article was originally published in the December 2023 issue.