Richseen Private Journeys · Caribbean

Caribbean Yacht Journey

Private Island Experience · St. Barths · Virgin Islands · Leeward Islands
8–10 Days · Caribbean
From USD 20,000+ per person
"The Caribbean by private yacht — St. Barths at dawn before the charter fleet arrives, the British Virgins' hidden coves, and the particular quality of December light on turquoise water that makes the winter escape most complete."
The Journey

The Caribbean,
Island to Island

The Caribbean in December and January is the most reliably perfect winter escape available from any northern hemisphere departure city — the trade winds blowing consistently from the northeast at 15 to 20 knots, the water temperature between 26 and 28°C, and the specific quality of the Caribbean winter light that the islands' position between the Atlantic and the Caribbean Sea produces in conditions no Mediterranean destination can replicate in the same months. The Leeward Islands — St. Barths, St. Martin, Anguilla, and the British Virgin Islands — constitute the most refined sailing circuit in the western hemisphere, where the island distances are short enough to make daily navigation practical and the individual island characters distinct enough to make each arrival a different experience.

The Caribbean Yacht Journey is structured around the specific character of the Leeward Islands circuit: St. Barths for the French Caribbean sophistication whose specific combination of St. Tropez beach culture, Parisian gastronomy, and the island's Swedish colonial history produces the most internationally recognised luxury destination in the Caribbean; Anguilla for the long-strand beaches whose sand quality exceeds any other island on the circuit and whose absence of a cruise ship port maintains the beach conditions that the resort infrastructure alone cannot produce; St. Martin/Sint Maarten for the French-Dutch cultural boundary that runs through the island's interior; and the British Virgin Islands for the Bitter End, the Baths on Virgin Gorda, and the sailing conditions in the Sir Francis Drake Channel that make the BVIs the yacht charter destination against which every other Caribbean circuit is measured.

This 8-to-10-day itinerary integrates the yacht with three of the Caribbean's most considered luxury addresses — Cheval Blanc St-Barth (LVMH's flagship Caribbean property on the Flamands beach); Eden Rock St Barths (the private rock formation hotel above the St. Jean bay); and Rosewood Little Dix Bay on Virgin Gorda (the 1964 Laurance Rockefeller resort whose reinvention by Rosewood maintains the Caribbean naturalist philosophy that defined the original property). The combination of the yacht's flexibility and the three hotels' individual character produces the most complete single Caribbean luxury experience available.

Signature Moments

Six Encounters
with the Caribbean

St. Barths at dawn before the charter fleet departs, Anguilla's Shoal Bay in December light, and the Baths on Virgin Gorda where the granite boulders meet the Caribbean Sea.

01
St. Barths at Dawn — The French Caribbean Before the Charter Fleet
St. Barths at 7am — the 21-square-kilometre island that France acquired from Sweden in 1878 (along with Gustavia, the capital named for the Swedish king Gustav III) and whose specific combination of French colonial administration, St. Tropez beach culture, and the 3,000-resident community that declined mass tourism produces the most consistently refined Caribbean experience. The Gustavia harbour before the charter yachts depart for the day; the Shell Beach below the port; and the Saline beach on the island's southern shore — the 800-metre crescent accessible only on foot whose sand quality and the low-season privacy make it the reference Caribbean beach for the guests who know the difference.
02
Anguilla's Shoal Bay — The Caribbean Beach Standard
Shoal Bay East on Anguilla — the 3-kilometre white sand beach consistently rated among the finest beaches in the Caribbean, whose powdered coral sand produces the specific turquoise water colour that the island's tourism infrastructure has been built around since the 1980s. Anguilla has no cruise ship port; the beach conditions at Shoal Bay are maintained by the absence of mass visitor infrastructure that every comparable Caribbean beach lacks in the same months. The anchor in the bay for the morning swim; the Dolce Vita beach bar lunch; and the sail back to St. Barths in the trade wind afternoon that makes the Anguilla channel one of the most satisfying single passages on the circuit.
03
The Baths, Virgin Gorda — Granite Boulders at the Caribbean Sea
The Baths National Park on Virgin Gorda's southern tip — the geological formation where house-sized granite boulders create the sea-cave pools and the grottoes whose combination of the Caribbean's turquoise water and the specific quality of the light filtering through the boulder formations produces the most distinctive single natural landscape in the Lesser Antilles. The boulders were deposited by volcanic activity 70 million years ago; the swimming conditions in the pools between them — calm, clear, and at 27°C — are the most specific natural swimming experience available in the BVI circuit. Most accessible by tender from the yacht anchored in the bay before the day-excursion boats arrive from Road Town.
04
Cheval Blanc St-Barth — LVMH's Caribbean Flagship
Cheval Blanc St-Barth on the Flamands beach — LVMH's Caribbean flagship whose 41 villas and suites on the most secluded beach on the island provide the most operationally complete luxury hotel experience in the Leeward Islands: the Métis restaurant, the spa, the private beach, and the yacht mooring arrangement that allows the yacht to anchor in Flamands Bay with the hotel accessible by tender. The LVMH standard applied to the Caribbean: the same philosophy that produced Cheval Blanc Paris and Cheval Blanc Randheli, whose specific service and design culture makes the Caribbean property instantly legible as part of the same family.
05
Sir Francis Drake Channel — The BVI's Defining Sail
The Sir Francis Drake Channel between Tortola and the British Virgin Islands' southern island chain — the 25-kilometre passage that the trade wind fills from the east in conditions that make the BVI the world's most popular bareboat charter destination and that the fully crewed private yacht uses most rewardingly: the consistent 15-to-20-knot wind, the flat water in the channel's lee, and the island horizons on both sides producing the most immediately satisfying Caribbean sail available on any circuit. Named for the English privateer who sheltered here in 1585; used by every yacht in the Lesser Antilles since.
06
Caribbean Cuisine — Lobster, Creole Spice, and Rhum Agricole
The Caribbean food programme across the circuit — the St. Barths lobster grilled over charcoal at the harbour fish restaurant in Gustavia (the island whose French administration maintains the food quality standard closest to the metropolitan tradition); the jerk chicken at the roadside pits in the British Virgins whose cooking method — the pimento wood smoke and the scotch bonnet marinade — has been continuous since the Taino people developed the technique; the rhum agricole from Martinique (the cane juice distillation that the French Caribbean maintains as the regional spirit standard) in the ti punch whose preparation the yacht's bar will have confirmed before departure. The cooking that the yacht's morning market stop makes most directly available.
Key Highlights

What Makes This Journey

01 ⛵
Private Yacht — Leeward Islands Circuit, 8–10 Days
A private yacht across the Leeward Islands — St. Barths, Anguilla, St. Martin, and the British Virgin Islands — in the trade wind conditions that make December and January the Caribbean's most reliable sailing season. The islands close enough for daily passages; the individual characters distinct enough to make each arrival a different experience. The yacht that makes island-hopping most rewarding: the ability to anchor in the private cove, reach the beach before the day-excursion boats, and move on at the pace the wind and the schedule permit.
02 🏝️
St. Barths, Anguilla, and the BVI — Three Island Characters
The Leeward Islands circuit's three most distinct island characters — St. Barths (French Caribbean sophistication, Gustavia harbour, Saline beach); Anguilla (no cruise ships, Shoal Bay's coral sand, the Caribbean beach standard); and the British Virgin Islands (the Baths' granite boulder grottoes, the Sir Francis Drake Channel, Rosewood Little Dix Bay). Three islands whose combination in a single yacht journey produces the most complete Caribbean experience available in the Lesser Antilles.
03 🌴
Three Caribbean Addresses — Cheval Blanc, Eden Rock, Little Dix Bay
Cheval Blanc St-Barth on the Flamands beach (LVMH's Caribbean flagship); Eden Rock St Barths on the volcanic rock formation above St. Jean bay (the most dramatically positioned hotel in the island); and Rosewood Little Dix Bay on Virgin Gorda (Laurance Rockefeller's 1964 naturalist resort, reinvented by Rosewood). Three addresses whose integration with the yacht programme makes each night ashore as distinctive as the sailing day that preceded it.
Sample Itinerary

Key Moments & Movements

The Caribbean yacht season peaks December to April; the trade winds blow most consistently from the northeast at 15–20 knots from November to May. The itinerary below represents the Leeward Islands circuit from St. Barths east to the British Virgin Islands. Total sailing distance approximately 250 nautical miles. Embarkation at Gustavia, St. Barths; disembarkation at Road Town, Tortola, or return to St. Barths based on departure logistics.

Every Richseen Caribbean yacht journey is individually crafted. Yacht specification, route variants, and hotel availability are confirmed at the time of booking. The flexible routing allows the itinerary to be adjusted based on wind conditions, preferred islands, and the client's pace preference.

Day 1
St. Barths Arrival — Eden Rock · Gustavia · St. Jean
Arrive at St. Jean Airport (the STOL approach over the hilltop that makes St. Barths landings the most memorable in commercial aviation) or by private charter from Juliana Airport on St. Martin (15 minutes). Check in to Eden Rock St Barths — the hotel built into the volcanic rock formation above the St. Jean bay, whose rock-top villa and the natural swimming pool in the volcanic formation below provide the most dramatically positioned accommodation on the island. Gustavia harbour for the evening — the pink-and-white colonial buildings, the superyachts, and the waterfront restaurants where the French Caribbean cooking tradition is most immediately accessible.
Eden Rock St Barths
Day 2
St. Barths — Saline Beach · Gustavia Embarkation · Cheval Blanc
Morning: the Saline beach — the 800-metre white sand crescent accessible only on foot from the parking area behind the salt pond, whose absence of beach service makes it the most undeveloped beach on St. Barths and the most specifically Caribbean in character. Embarkation from Gustavia harbour in the early afternoon; the yacht briefing and the first trade wind sail. Cheval Blanc St-Barth on the Flamands beach for the overnight on the hotel's private beach — the Métis restaurant dinner; the infinity pool above the Flamands bay; and the first full view of the Caribbean stars from the beach that the island's absence of light pollution makes most vivid.
Cheval Blanc St-Barth / Aboard Yacht
Day 3
Anguilla — Shoal Bay · Cap Juluca · Meads Bay
Sail northwest from St. Barths to Anguilla (25 nautical miles, 3 hours). The approach to Shoal Bay East — the 3-kilometre coral sand beach whose turquoise water and the absence of cruise ship infrastructure maintain the beach conditions that every other accessible Caribbean beach has lost. Morning anchor and swim; the Dolce Vita beach bar lunch on the sand. Cap Juluca on the western shore for the afternoon — the Moroccan-arched resort whose Maundays Bay position provides the most dramatic sunset view available on the island, looking back toward St. Barths and St. Martin across the channel. Sail back east toward St. Martin for the overnight anchor.
Aboard Yacht · Anguilla
Day 4
St. Martin / Sint Maarten — Marigot · Orient Bay · Island Border
St. Martin — the island divided since 1648 between France (Saint-Martin, northern two-thirds) and the Netherlands (Sint Maarten, southern third) by the shortest international land border in the world (10.2 kilometres), established by the legend of a Frenchman and a Dutchman walking in opposite directions from the same point until they met. Marigot on the French side for the morning market and the Fort Saint-Louis view; Orient Bay on the northeastern coast for the afternoon anchor — the beach whose 2-kilometre length and the barrier reef conditions make it the most complete beach day available on the island. Sail east toward St. Barths for the final night before the BVI passage.
Aboard Yacht · St. Martin
Day 5
Passage — St. Barths to Tortola · Sir Francis Drake Channel
The longest passage of the itinerary — St. Barths east to Tortola in the British Virgin Islands (75 nautical miles, 7 to 8 hours in the trade wind). The Anegada Passage between the Leeward Islands and the BVI — the deep-water channel where the Atlantic swell and the trade wind combine to produce the most open-ocean sailing conditions on the circuit. Norman Island for the afternoon anchor — the island reputed to be the model for Robert Louis Stevenson's Treasure Island (1883), whose caves on the western shore are accessible by dinghy and whose underwater conditions in the Treasure Caves are among the most colourful snorkelling in the BVI.
Aboard Yacht · BVI Passage
Day 6
Virgin Gorda — The Baths · Rosewood Little Dix Bay
Sail east along the Sir Francis Drake Channel to Virgin Gorda — the 25-kilometre passage in trade wind conditions that makes the BVI the world's most popular yacht charter destination. The Baths National Park on Virgin Gorda's southern tip: the tender landing and the walk through the granite boulder grottoes to the Devil's Bay beach, whose combination of the boulder formations, the turquoise pool grottoes, and the Caribbean Sea visible through the rock arches produces the most distinctive natural landscape in the Lesser Antilles. Check in to Rosewood Little Dix Bay on the northern shore for the overnight — the 1964 Laurance Rockefeller resort whose Caribbean naturalist philosophy the Rosewood renovation has maintained.
Rosewood Little Dix Bay, Virgin Gorda
Day 7
BVI — Jost Van Dyke · White Bay · Soggy Dollar Bar
Sail northwest to Jost Van Dyke — the 8-square-kilometre island whose population of 300 maintains the Caribbean social infrastructure most directly: the Soggy Dollar Bar on White Bay (established 1970, where the Painkiller cocktail — Pusser's rum, cream of coconut, orange juice, pineapple juice, freshly grated nutmeg — was invented and where the swim-up bar entrance from the boat requires wading through shallow water, hence the dollar's condition). White Bay's horseshoe beach at the hour before the day-trip boats arrive. The overnight anchor in Great Harbour below Ivan's Stress Free Bar for the final night under the BVI stars.
Aboard Yacht · Jost Van Dyke
Day 8–10
Disembarkation · Return to St. Barths or Tortola Departure
Final days at the pace the remaining schedule allows — the BVI's eastern islands (Anegada, the flat coral island whose horseshoe reef is the second-largest barrier reef in the western hemisphere and whose lobster grilled on the beach constitutes the most specifically Caribbean single meal on the circuit) for guests extending to 10 days; or the return passage west to St. Barths for the final night at Cheval Blanc before the charter aircraft to Juliana or the direct connections from Gustavia. Disembarkation at Road Town, Tortola, for direct connections to Miami, New York, or London.
BVI / Departure Airport
Luxury Stays

Where You Rest Matters

Flamands Beach, St. Barths
St. Barths — 2 Nights
Cheval Blanc St-Barth
Anse des Flamands, 97133 St. Barthélemy
Cheval Blanc St-Barth — LVMH's flagship Caribbean property on the Flamands beach, whose 41 villas and suites, the Métis restaurant, the spa, and the private beach provide the most operationally complete luxury hotel experience in the Leeward Islands. The yacht mooring arrangement in Flamands Bay allows the yacht and the hotel to be used simultaneously — the most practical integration of boat and land-based programme available on the island. The LVMH standard applied to the Caribbean: the same design and service philosophy as Cheval Blanc Paris, whose specific culture makes the property instantly legible as part of the same family.
St. Jean Bay, St. Barths
St. Barths — 1 Night (Arrival)
Eden Rock St Barths
Baie de St. Jean, 97133 St. Barthélemy
Eden Rock St Barths — the hotel built into the volcanic rock formation above the St. Jean bay, whose rock-top villa and the swimming pool in the natural volcanic formation below provide the most dramatically positioned accommodation on the island. Founded by British racing driver David Matthews in 1995 when he purchased the rock formation and built his private house on it; converted to a hotel whose rock-top villa suite and the artistic collection that Matthews assembled define the property's character. The St. Jean bay visible from every room; the Eden Rock beach bar below; and the rock-face path between the two levels that makes the hotel's topography its most distinctive feature.
Little Dix Bay, Virgin Gorda, BVI
Virgin Gorda — 1 Night
Rosewood Little Dix Bay
Little Dix Bay, Virgin Gorda, British Virgin Islands
Rosewood Little Dix Bay — the 1964 Laurance Rockefeller resort whose Caribbean naturalist philosophy (minimal environmental impact, the integration of the resort into the surrounding landscape, and the specific quality of the Virgin Gorda hillside setting above the bay) the Rosewood renovation has maintained and elevated. The Little Dix Bay itself — the crescent beach with the BVI's clearest water in the cove's protected conditions; the Reef House restaurant; and the surrounding national park trails that Rockefeller's original land donation preserved as the natural context the resort requires. The BVI address whose combination of design quality and landscape setting makes it the most considered single hotel in the British Caribbean.
Exclusive Experiences

Moments Designed for You

⛵
Yacht
Leeward Islands Circuit — Trade Wind Sailing, Private Coves
A private yacht across the Leeward Islands in the trade wind season — the consistent northeast wind at 15 to 20 knots providing the sailing conditions that make the Caribbean circuit most rewarding in December through April. The ability to anchor in the private cove before the day-excursion boats arrive; to reach the beach accessible only by water; and to move between islands at the pace the wind and the schedule permit. The circuit whose individual island characters — French Caribbean, British, Dutch, no-cruise-ship — make each day's destination distinct from the previous one.
🏖️
Beaches
Saline, Shoal Bay, and White Bay — The Caribbean Beach Standards
Three beaches whose combination in a single yacht journey produces the most complete Caribbean beach programme available: Saline on St. Barths (no beach service, accessible only on foot, the most undeveloped beach on the most refined island); Shoal Bay East on Anguilla (3 kilometres of coral sand, no cruise ships, the Caribbean beach standard); and White Bay on Jost Van Dyke (the horseshoe beach with the Soggy Dollar Bar, the Painkiller at source, the swim-in access that makes the bar most itself). The beaches most themselves in the conditions that the yacht's morning arrival makes accessible before the daily visitor cycle begins.
💎
The Baths
Virgin Gorda's Granite Grottoes — By Tender Before the Day-Trips
The Baths National Park on Virgin Gorda — the geological formation whose granite boulder grottoes, Caribbean turquoise pool passages, and the Devil's Bay beach beyond constitute the most distinctive single natural landscape in the Lesser Antilles. Accessed by tender from the yacht anchored in the bay before the day-excursion boats arrive from Road Town — the timing that makes the boulder pools available in the conditions of early morning light and minimal visitor presence that the park's geological quality most deserves. The 70-million-year-old granite boulders; the 27°C water in the natural pools between them; and the Caribbean Sea visible through the rock arches at the passage's end.
🦞
Caribbean Cuisine
Lobster, Painkiller, and the Soggy Dollar — Caribbean at Source
The Caribbean food programme across the circuit — the St. Barths lobster grilled at the Gustavia harbour restaurants whose French Caribbean cooking standard makes the island the most culinarily consistent in the Leewards; the Anegada lobster grilled on the beach at the fishing village whose horseshoe reef produces the most abundant single lobster catch in the BVI; the Painkiller cocktail at its source at the Soggy Dollar Bar on White Bay, Jost Van Dyke; and the onboard cooking using the morning's market produce from each port. The ti punch in the trade wind evening — rhum agricole from Martinique, lime, cane syrup — prepared on the yacht at anchor in conditions that make the drink most comprehensible as the Caribbean's defining aperitif.
Visual Journey

Through the Lens

Begin Your Story

Craft Your
Private Journey

Every detail — from your first morning at Saline beach to your final trade wind sail back from the Baths — is composed entirely around you. Speak with your dedicated Richseen journey consultant today.

From USD 20,000+ per person

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