Private Villa Journey
A fully-staffed villa above a turquoise bay, with a private chef. A private, tailored journey of 7-10 days in The Caribbean, designed end to end by a Forest Travel advisor — with Virtuoso privileges at the finest luxury hotels, from US$11,000 per traveler.
- Villa
- 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$11,000 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 fully-staffed villa above a turquoise bay, with a private chef. A private, tailored journey of 7-10 days in The Caribbean, designed end to end by a Forest Travel advisor — with Virtuoso privileges at the finest luxury hotels, from US$11,000 per traveler.
Few places pair such effortless turquoise beauty with the depth of privacy and service the islands quietly reserve for their most valued guests.
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 chef designing each menu around the morning catch and produce from nearby markets.
- A crewed day yacht slipping out to secluded coves and neighbouring cays.
- In-villa spa treatments arranged on the terrace as the light softens over the water.
- A tasting of island rums and small-batch spirits led by a private sommelier.
A sense of the rhythm
Days settle into an unhurried rhythm shaped entirely by you. Mornings drift between the pool and the shoreline, afternoons open to a boat or simply the shade of the terrace, and evenings belong to the chef and the sound of the sea. Nothing is scheduled that you did not choose.
St Barth or Anguilla for a villa base?
St Barth rewards those who want a little glamour within reach, with its harbour, its tables and its polished energy. Anguilla is quieter and more expansive, with longer beaches and a deeper sense of seclusion. We match the island to the mood you are after.
How to do it well
The counsel our advisors give travelers planning this journey:
- Book the villa and its full staff well ahead for the December to April window, when the finest homes are claimed early.
- Ask us to stock the villa in advance so the pantry and cellar reflect your tastes from the first evening.
- Keep one day free for a spontaneous yacht charter when the weather is perfect.
- Confirm private airport transfers on both islands to avoid the ferry crowds entirely.
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$11,000 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 Private Villa Journey around you — privately, every Virtuoso privilege included. Request your private consultation →
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$11,000 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.
St Barth rewards those who want a little glamour within reach, with its harbour, its tables and its polished energy. Anguilla is quieter and more expansive, with longer beaches and a deeper sense of seclusion. We match the island to the mood you are after.
A private chef designing each menu around the morning catch and produce from nearby markets. A crewed day yacht slipping out to secluded coves and neighbouring cays. In-villa spa treatments arranged on the terrace as the light softens over the water. Everything is private and shaped to you.
Book well ahead. Our advisors recommend securing the villa and its full staff early for the December to April window, because that is when the finest homes are claimed first. Those months bring dry, sun-warmed days and calm seas, which is exactly why demand gathers there. Your advisor times the booking to the light, the crowds and your own calendar, so the right home is held for you.
Yes. Ask us to stock the villa in advance, and the pantry and cellar will reflect your tastes from the first evening. From there, your private chef designs each menu around the morning catch and produce from nearby markets, and the journey can include a tasting of island rums and small-batch spirits led by a private sommelier. Evenings belong to the chef and the sound of the sea.
Confirm private airport transfers on both islands. That is the counsel our advisors give travelers planning this villa journey, and it lets you avoid the ferry crowds entirely. Your Forest Travel advisor arranges the transfers as part of a journey designed end to end, and stays one message away before and throughout your trip, so arrivals feel as private and unhurried as the days at the villa.
A day at a fully-staffed Caribbean villa in St Barth or Anguilla follows an unhurried rhythm shaped entirely by you. Mornings drift between the pool and the shoreline, afternoons open to a boat or simply the shade of the terrace, and evenings belong to the private chef and the sound of the sea. Nothing is scheduled that you did not choose, so each day can be as active or as still as you wish.
On a private villa journey to St Barth or Anguilla, our advisors suggest keeping one day free for a spontaneous yacht charter when the weather is perfect. A crewed day yacht can slip out to secluded coves and neighbouring cays, and leaving the date open lets you choose the calmest, brightest day. December through April, with its calm seas, is the ideal window for time on the water.
Yes. On a private villa journey in St Barth or Anguilla, spa treatments can be arranged in the villa itself, on the terrace as the light softens over the water. Like every experience on this journey, they are arranged privately and shaped to you, so they fit into an unhurried day between the pool, the shoreline and an evening with the private chef.
The Caribbean
See the collection →Tell a private advisor how you like to travel — no quotes, no obligation.
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