St Martin, Anguilla and the Cays

The island as a base rather than a destination: a crewed day to Anguilla's beaches, another to the uninhabited cays offshore, and a lagoon behind you that shelters more yachts than anywhere else in the region. A private, tailored journey of 8 Days · 7 Nights in St Martin, The Caribbean, designed end to end by a Forest Travel advisor — with Virtuoso privileges at the finest luxury hotels, from US$12,500 per traveler.

Few places pair such effortless turquoise beauty with the depth of privacy and service the islands quietly reserve for their most discerning 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 privately chartered catamaran or monohull, crewed and provisioned, positions you each morning for a different anchorage — Anguilla's Shoal Bay, the Dog Island passage, or the glassy shallows of Tintamarre — with no itinerary fixed until you decide over coffee.
• A curated crossing to Anguilla's west-end beach bars, arranged with shore-side dining reservations at Hibernia or Blanchards so the day moves seamlessly from sea to table.
• Full access to Simpson Bay Lagoon's superyacht infrastructure — fuel, provisions, certified dive guides and water-toy charters organized through a single concierge contact before you arrive.
• A private snorkel or shallow-dive circuit around the uninhabited cays offshore, guided by a marine naturalist who reads the current and tide so visibility is always at its peak.

A sense of the rhythm

Days begin at anchor, unhurried, with the crew handling everything from coffee to the dinghy launch while you decide whether to swim first or sail first. By midday you are somewhere unreachable by road — a sandbar, a cay, an Anguillan bay — and by evening you have the choice of returning to a marina berth for dinner ashore or staying out under stars. The pace is entirely yours to set, and the crew's job is to make each option feel equally effortless.

Whether to base the trip on a live-aboard charter or to split nights between the yacht and a shoreside property

A full live-aboard charter gives you the greatest range — you wake where you anchored, and a day sail to Anguilla or the cays costs nothing extra in logistics. Splitting your nights, however, lets you enjoy a larger stateroom experience on land and frees the crew to reposition the vessel and restock provisions while you dine ashore at Grand Case or sleep in a full-sized suite. The right answer depends on whether you value seamless mobility or the option to step off and decompress in a fixed space; we map the hybrid itinerary that serves both without diluting either.

How to do it well

The counsel our advisors give travelers planning this journey:

• Book your crewed charter at least four to five months ahead for the December-to-April high season — the finest bareboat and crewed vessels based in Simpson Bay Lagoon are reserved by September by repeat clients.
• The Anguilla day crossing requires a departure stamp from St Martin and an Anguillan arrival fee; we handle the paperwork and pre-clear customs contacts so the transit takes minutes rather than an afternoon.
• Schedule your cay anchorages for weekday mornings — Tintamarre and Pinel in particular draw day-trip boats from Friday to Sunday, and an early-week position gives you the water almost entirely to yourself.
• If your dates fall around the Heineken Regatta in late February or early March, plan the offshore cay days for that window — the lagoon and marinas are full and festive, but the uninhabited anchorages remain perfectly quiet.

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$12,500 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 St Martin

Part of our St Martin travel guide. Related private journeys:

• The Grand Case Table
• A Villa on the French Side
• A Long Weekend, Both Sides

Begin the conversation

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