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Yacht Escape

Yacht Escape

A crewed yacht between empty anchorages and beach-bar lunches.

Curated by Juan David· Travel Agent, Forest Travel· Updated July 2026
Key takeaways
  • Yacht · Sail
  • Ideal length: 7-10 days
  • Best time: December through April brings dry, sun-warmed days and calm seas, the ideal window before the summer humidity and hurricane months arrive.
  • Private guiding, access and transfers throughout
  • From US$15,000 per traveler — a starting point, tailored to you
  • Designed one-to-one by a Forest Travel advisor
  • Virtuoso privileges at the finest luxury hotels

A crewed yacht between empty anchorages and beach-bar lunches.

Few places pair such effortless turquoise beauty with the depth of privacy and service the islands quietly reserve for their most discerning guests.

Yacht Escape — The Caribbean

When to go

December through April brings dry, sun-warmed days and calm seas, the ideal window before the summer humidity and hurricane months arrive. Your advisor times it to the light, the crowds and your own calendar.

The experiences

A sense of what this journey can hold — each one arranged privately and shaped to you:

  • A private crew who chart each day around the anchorages you most want to find.
  • Beach-bar lunches reached only by tender, with your table waiting on the sand.
  • Snorkelling and diving over reefs far from any other boat.
  • Sundowners on deck as you swing quietly at anchor off an empty cay.

A sense of the rhythm

Life aboard follows the sea rather than the clock. You wake wherever the last evening left you, choose the day over breakfast, and let the crew handle everything between one anchorage and the next. The islands slip past on your own terms, with the freedom to stay or move as the mood takes you.

The Virgin Islands or the Grenadines to cruise?

Around St Thomas and the Virgins, short hops and sheltered water make for easy, sociable sailing. The Grenadines to the south are wilder and more remote, with longer passages and far fewer boats. We route the charter to match the sailing you have in mind.

How to do it well

The counsel our advisors give travelers planning this journey:

  • Match the yacht to your party rather than the itinerary, then build the route around it.
  • Sail in the drier winter months for steadier trade winds and calmer anchorages.
  • Let the crew keep one day flexible for the anchorage that turns out to be everyone's favourite.
  • Tell us your preferences in advance so the galley and cellar are exactly as you like them.

What only your advisor can open

The difference between a good trip and an unrepeatable one is access — and access is a relationship, not a booking. Every guide, room and moment is chosen and sequenced for you.

Who it's for

Travelers who value privacy, time and doing it once — beautifully — and who would rather have one trusted advisor orchestrate every detail than assemble it themselves.

Estimated investment

From US$15,000 per traveler, based on double occupancy — scaled to your dates, party size and level of privacy. A starting point, not a final quote; confirmed once your advisor tailors the itinerary.

Designed entirely around you

Nothing here is a package. A Forest Travel advisor shapes the whole journey and stays one message away before and throughout your trip.

Your Virtuoso privileges

As a Virtuoso member, Forest Travel includes benefits reserved for Virtuoso guests at the finest luxury hotels, at no added cost: a room upgrade on arrival when available, daily breakfast for two, a property credit toward dining or spa, and early check-in with late check-out when the hotel allows.

Continue exploring The Caribbean

Part of our The Caribbean travel guide. Related private journeys:

Begin the conversation

Tell a Forest Travel advisor how you like to travel and they will design Yacht Escape around you — privately, every Virtuoso privilege included. Request your private consultation →

Common Questions

Questions, answered.

We suggest 7-10 days to do it without rushing — enough for the private guiding, the unhurried mornings and a little room to simply be there. Your advisor tunes the length to your calendar and pace.

As a private, tailored journey it starts from roughly US$15,000 per traveler (double occupancy) and scales with your dates, party and level of privacy — a starting point, never a fixed package price. Your advisor confirms the figure once the itinerary is tailored.

December through April brings dry, sun-warmed days and calm seas, the ideal window before the summer humidity and hurricane months arrive. Your Forest Travel advisor times it to the light, the seasons and your calendar.

Around St Thomas and the Virgins, short hops and sheltered water make for easy, sociable sailing. The Grenadines to the south are wilder and more remote, with longer passages and far fewer boats. We route the charter to match the sailing you have in mind.

A private crew who chart each day around the anchorages you most want to find. Beach-bar lunches reached only by tender, with your table waiting on the sand. Snorkelling and diving over reefs far from any other boat. Everything is private and shaped to you.

Yes — because it is built from scratch for your party, it adapts to honeymoons, milestone celebrations, and multigenerational families alike, with the pace, privacy and comfort set to your group.

A Virtuoso member like Forest Travel unlocks room upgrades, daily breakfast, hotel credits and early/late check-out at the finest hotels, plus a dedicated advisor who designs and manages the whole journey — access and service a booking engine can't match.

Explore the journeys

The Caribbean

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Tell a private advisor how you like to travel — no quotes, no obligation.

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