Ideal for Winter Season
Spanning two sovereign territories and more than 60 islands within easy sailing distance of each other, this eight-day circuit from St Thomas moves through both the US and British Virgin Islands, crossing the Sir Francis Drake Channel to take in the cave diving of Norman Island, to the sunken plane wreck off St John and the legendary beach bars of Jost Van Dyke. It is one of the most complete introductions to Caribbean yacht charter sailing available anywhere in the region, combining the national park landscapes of the USVI with the sailing culture, wreck dives, and unspoilt anchorages of the BVI in a single, unhurried week on the water.
- Day 1
Embark in St Thomas
The gateway to the Virgin Islands and one of the Caribbean's finest natural harbors
Embark on your St Thomas yacht charter at Crown Bay Marina, one of the best-equipped superyacht facilities in the US Virgin Islands, with stunning views across the harbor from the moment you step aboard. St Thomas is consistently ranked as the most popular embarkation point in the US Virgin Islands for good reason: its combination of duty-free shopping, world-class beaches, and outstanding sailing conditions makes it a destination in its own right rather than simply a departure gate.
Take the afternoon to explore before setting sail. The Skyride to Paradise Point offers a gondola ride above the harbor with panoramic views over Charlotte Amalie, the island's capital and one of the best duty-free shopping destinations in the Caribbean.
Magens Bay on the island's north shore is widely considered one of the most beautiful beaches in the Caribbean, a heart-shaped bay of calm, shallow water and soft white sand that rewards an hour's visit before returning to the yacht. Water sports conditions around St Thomas are exceptional; the afternoon is ideal for jet skiing or paddleboarding directly from the marina before the crew prepares the first dinner of the week on deck.
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Skyride to Paradise Point
Attraction
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Magens Bay
Beach
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Skyride to Paradise Point
- Day 2
St John
Two-thirds national park, world-class snorkeling, and a sunken plane dive
The shortest crossing of the week brings you to St John, the smallest of the three main islands of a US Virgin Islands yacht charter, and the most naturally pristine, with approximately two-thirds of the island and its surrounding waters protected within the Virgin Islands National Park. The result is a coastline in extraordinary condition, a marine environment of exceptional diversity, and hiking trails through untouched tropical forest that offer a genuine counterpoint to the yacht-based days on either side.
Begin with a morning walk through the national park's clearly marked trails while keeping watch for the island's resident wildlife, including mongoose, white-tailed deer, and over 160 bird species that inhabit the protected interior. Trunk Bay is the island's most celebrated beach, and an underwater snorkel trail marked with plaques identifying the coral and marine species makes it one of the most educational snorkeling experiences in the charter routes of St John.
In the afternoon, Francis Bay holds a sunken plane wreck dive, still largely intact, attracting a remarkable community of marine life, and accessible to all experience levels. Waterlemon Cay nearby is a strong alternative for snorkeling, with one of the most consistently rewarding reef environments in the USVI.
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Waterlemon Cay
Beach
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Trunk Bay
Beach
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Waterlemon Cay
- Day 3
Norman Island
The Treasure Island original, a floating pirate bar, and the BVI's best cave diving
Cross the Sir Francis Drake Channel into British Virgin Islands waters and arrive at Norman Island, the uninhabited island widely believed to have inspired Robert Louis Stevenson's Treasure Island, and one of the most characterful stops on any BVI yacht charter. The pirate mythology here is more than just marketing; the island has a documented history of buried treasure, and the caves along its western cliff face were reportedly used to store plundered goods.
Willy T, a decommissioned Baltic trader permanently moored in the anchorage and converted into one of the Caribbean's most legendary floating bars, is an essential stop, even for those who arrived purely for the diving. The real draw underwater is The Caves at Treasure Point: three sea caves accessible by snorkel or dive, illuminated by shafts of light that filter through the rock and home to glassy sweepers, squirrelfish, and octopus tucked into the reef structure.
The Indians, four rocky pinnacles rising from open water just offshore, offer some of the finest shallow snorkeling in the BVI, with dense hard coral coverage and abundant reef fish at accessible depths. Spend the evening at anchor on your chosen luxury yacht charter in The Bight and dine at the Pirates Beach Bar ashore.
- Day 4
Peter Island
One of the Caribbean's finest beaches, a bay named for drowned pirates, and green sea turtle encounters
An early arrival at Peter Island secures the best anchorage position. This largely private island south of Tortola draws significant yacht traffic through the season, and the morning hours are the most peaceful. The island's beaches consistently rank among the finest in the Virgin Islands yacht charters circuit, and the morning is best spent doing very little: settling into the soft white sand, swimming in clear turquoise water, and watching the Sir Francis Drake Channel light up as the sun climbs.
Deadman's Bay carries a darker history than its pristine setting suggests, named for the bodies of pirates washed ashore after reportedly attempting the swim from Dead Chest Island nearby, the subject of the seafaring rhyme that gave us "Fifteen men on a dead man's chest, yo-ho-ho and a bottle of rum."
The dive conditions here offer a more peaceful encounter: green sea turtles are regularly spotted in the waters off Peter Island's eastern shore, and the bay's calm, clear conditions make underwater camera work genuinely rewarding. Spend the afternoon at leisure on the water before the overnight passage to Virgin Gorda.
- Day 5
Virgin Gorda
The BVI's most iconic geological wonder and its finest resort anchorage
Virgin Gorda is the highlight stop of any Virgin Islands yacht charter itinerary, an island of dramatic contrasts between the boulder-strewn southwestern shore and the calm, sheltered waters of the North Sound. Begin at The Baths, a geological formation unique in the Caribbean, where enormous granite boulders create a labyrinth of grottos, tunnels, and tidal pools along the shoreline. The salt water inside reaches near-perfect temperature by mid-morning, and the filtered light through the boulders creates an atmosphere that rewards slow exploration.
In the afternoon, the crew will escort you north to the North Sound and the Bitter End Yacht Club, a landmark institution in BVI sailing culture, offering day access to its water sports facilities, beach bar, and restaurant.
Round off the day of your Virgin Gorda yacht charter with dinner at the Saba Rock Resort, a small private island in the North Sound accessible only by water taxi, with a restaurant, bar, and exceptional views across the anchorage that make for one of the finest dining settings in the Virgin Islands.
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Gorda Peak National Park
Attraction
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The Baths
Landmark
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Gorda Peak National Park
- Day 6
Marina Cay
A picture-perfect private cay, a world-class reef, and one of the most peaceful anchorages in the BVI
Marina Cay sits just off the eastern tip of Tortola, a small, jewel-like island that was famously the subject of Robb White's 1953 memoir Our Virgin Island, later adapted into a film starring Sidney Poitier. Today it remains one of the quietest and most naturally beautiful stops on any motor or sailing yacht charter in the BVIs, with an unhurried quality that makes it an ideal counterpoint to the more social stops earlier in the week.
The reef system off Great Camanoe to the west is the diving highlight, a densely populated coral garden with vibrantly colored formations, large schools of tropical fish, and good visibility that makes it consistently rewarding for both snorkelers and divers.
Pusser's at Marina Cay on the island's waterfront is the natural choice for lunch or dinner, a relaxed Caribbean institution serving the famous Pusser's Rum in a setting that looks out across the Sir Francis Drake Channel toward the outer BVI islands. Spend the evening at anchor in the calm waters around the cay before the final overnight passage toward Jost Van Dyke.
- Day 7
Jost Van Dyke
The social soul of the BVI, a natural whirlpool, and the Caribbean's most celebrated beach bar
Small in geography but enormous in character, Jost Van Dyke is the social center of the Jost Van Dyke yacht charter circuit and one of those stops that defines a Virgin Islands vacation. Begin at White Bay Beach, a long sweep of pale sand on the island's south shore, home to Foxy's Bar, which has been hosting charter guests and sailors since the 1960s and remains the most celebrated beach bar in the Caribbean. The beach barbecue on weekend evenings, with live music and cold rum drinks, is one of those genuinely unhurried Caribbean experiences that stays with you.
Great Harbour along the south coast offers a more cosmopolitan alternative, a waterfront strip of bars and casual restaurants that comes alive through the afternoon. Before leaving the island, make the tender trip to Bubbly Pool at the northeastern tip, a natural rock pool where Atlantic wave surge creates a Jacuzzi effect in the shallows, the perfect way to close out the last full day in the Virgin Islands.
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White Bay Beach
Beach
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Foxy's Bar
Bars
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White Bay Beach
- Day 8
Return to St Thomas
A final morning on the water before the journey home
Your chosen Caribbean charter yacht makes its final passage back to St Thomas yacht charters' home base at Crown Bay Marina, completing this eight-day circuit through both the US and British Virgin Islands. Have a leisurely breakfast on deck and take a last swim off the stern before heading ashore; the particular quality of light over the harbor in the morning is worth absorbing one final time.
If flight times allow, Charlotte Amalie, St Thomas's capital and one of the finest duty-free shopping destinations in the Caribbean, is worth a final hour's browse for jewelry, local rum, and handcrafted souvenirs.
For those wanting a more relaxed close to the week, a massage at one of the harbor-side spa facilities near Crown Bay provides a fittingly unhurried end to an exceptional eight days across the British Virgin Islands and USVIs.
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*All distances are approximate
