A Long Weekend, Both Sides
Short enough to be spontaneous, on the one island where a twenty-minute drive changes the country, the language and the menu. The French side to sleep, the Dutch side for the evening that runs late. A private, tailored journey of 5 Days · 4 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$4,200 per traveler.
- Ideal length: 5 Days · 4 Nights
- 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$4,200 per traveler — a starting point, tailored to you
- Designed one-to-one by a Forest Travel advisor
- Virtuoso privileges at the finest luxury hotels
Short enough to be spontaneous, on the one island where a twenty-minute drive changes the country, the language and the menu. The French side to sleep, the Dutch side for the evening that runs late. A private, tailored journey of 5 Days · 4 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$4,200 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 privately arranged sunrise sail from Marigot Bay that returns you to the French side in time for a late breakfast at a hillside table above the lagoon.
- A guided crossing into the Dutch quarter of Philipsburg, timed to the weekly open-air market, with a curator who knows which vendors carry genuine Antillean craft rather than resort merchandise.
- A half-day arranged with a local freediver off Tintamarre Island, with a private lunch set up on the uninhabited shore afterward.
- An evening itinerary on the Dutch side that moves from a sunset cocktail on the Boardwalk through dinner at a Pelican Key terrace and into whichever room is running late that night — logistics handled entirely by us.
A sense of the rhythm
The pace divides naturally: mornings belong to the French side, where the roads are quieter and the rhythm is unhurried, and late afternoons belong to the crossing east toward Sint Maarten, where the energy builds through sundown. By the fifth morning you have lived two distinct Caribbean registers without once leaving the island.
Whether to base the whole stay on the French side or split nights between the two
For a long-weekend structure, we consistently recommend sleeping in Terres Basses or Orient Bay on the French side — the finest luxury hotels there offer a quieter setting and a more considered breakfast culture that sets the morning tone. The Dutch side rewards the evening, not the pillow: Maho, Simpson Bay and the Boardwalk are best experienced as a destination you drive to and return from. Splitting nights introduces check-in friction and lost luggage time that a five-night itinerary cannot absorb comfortably. One base, two sides — that is the architecture of this particular archetype.
How to do it well
The counsel our advisors give travelers planning this journey:
- Book the finest luxury hotels on the French side at least sixty days out for travel between December and April; inventory at the level we place clients runs to single digits during peak weeks.
- The border between Marigot and Philipsburg has no formal crossing but the road through Cole Bay slows considerably on Friday afternoons — build any Dutch-side dinner reservation around a 6 p.m. departure from your hotel, not later.
- Tintamarre Island excursions require advance coordination with licensed marine operators; we arrange permits and a private vessel so the shore lunch does not share the beach with a catamaran crowd.
- February through early April is the sweet window: the trade winds are steady for sailing, the rainy-season humidity has not arrived, and the Grand Case restaurant season — which your itinerary deliberately does not lean on, since that archetype lives elsewhere on this page — is at full strength if you choose to cross for one meal.
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$4,200 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:
Begin the conversation
Tell a Forest Travel advisor how you like to travel and they will design A Long Weekend, Both Sides around you — privately, every Virtuoso privilege included. Request your private consultation →
Questions, answered.
For a long-weekend structure, we consistently recommend sleeping in Terres Basses or Orient Bay on the French side — the finest luxury hotels there offer a quieter setting and a more considered breakfast culture that sets the morning tone. The Dutch side rewards the evening, not the pillow: Maho, Simpson Bay and the Boardwalk are best experienced as a destination you drive to and return from. Splitting nights introduces check-in friction and lost luggage time that a five-night itinerary cannot absorb comfortably. One base, two sides — that is the architecture of this particular archetype.
It is roughly a twenty-minute drive, and the border between Marigot and Philipsburg has no formal crossing. The one thing to plan around is traffic: the road through Cole Bay slows considerably on Friday afternoons. For any Dutch-side dinner reservation, build the evening around a 6 p.m. departure from your hotel, not later, so the sunset cocktail on the Boardwalk is not lost to the road.
Yes. Tintamarre Island excursions require advance coordination with licensed marine operators, and Forest Travel arranges the permits and a private vessel for you. The half-day is spent with a local freediver off the island, followed by a private lunch set up on the uninhabited shore, timed so it does not share the beach with a catamaran crowd.
At least sixty days out. For travel between December and April, inventory at the finest luxury hotels on the French side, at the level Forest Travel places clients, runs to single digits during peak weeks. Terres Basses or Orient Bay is the recommended base for this long weekend, with its quieter setting and a more considered breakfast culture that sets the morning tone.
A Long Weekend, Both Sides is designed as 5 Days · 4 Nights, from one base on the French side, in Terres Basses or Orient Bay. Mornings belong to the French side, with quieter roads and an unhurried rhythm: a private sunrise sail from Marigot Bay with a late breakfast above the lagoon, or a half-day with a freediver off Tintamarre Island. Late afternoons belong to the crossing east toward Sint Maarten, for the Philipsburg market or an evening from the Boardwalk to a Pelican Key terrace. By the fifth morning you have lived two distinct Caribbean registers without leaving the island.
As a private, tailored journey it starts from roughly US$4,200 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, before the summer humidity and hurricane months arrive. For this journey, February through early April is the sweet window: the trade winds are steady for the sunrise sail from Marigot Bay, the rainy-season humidity has not arrived, and the Grand Case restaurant season is at full strength if you choose to cross for one meal. Book French-side hotels at least sixty days out for these months.
The sunrise sail from Marigot Bay is arranged privately and returns you to the French side of St Martin in time for a late breakfast at a hillside table above the lagoon. It belongs to the French-side mornings of A Long Weekend, Both Sides, when the roads are quieter and the rhythm is unhurried. From February through early April the trade winds are steady for sailing, which makes it the sweet window for this outing.
On A Long Weekend, Both Sides, the crossing into the Dutch quarter of Philipsburg is guided and timed to the weekly open-air market. You go with a curator who knows which vendors carry genuine Antillean craft rather than resort merchandise, so your time is spent on real local work. It is arranged privately and is one of the ways the journey shows you the Dutch side of St Martin.
A Dutch-side evening on St Martin moves from a sunset cocktail on the Boardwalk to dinner at a Pelican Key terrace, then into whichever room is running late that night, with all logistics handled by Forest Travel. The Dutch side rewards the evening, not the pillow: Maho, Simpson Bay and the Boardwalk are places you drive to and return from, while you sleep on the quieter French side.
Not as a centrepiece. A Long Weekend, Both Sides deliberately does not lean on the Grand Case restaurant season, which belongs to a different style of St Martin journey. If you choose to cross for one meal, February through early April is when that season is at full strength, and it is also the sweet window for steady trade winds, before the rainy-season humidity arrives.
St Martin suits a long weekend well: five days and four nights give you two countries on one island, with the French side to sleep and the Dutch side for the evening, about twenty minutes apart by car. A sunrise sail from Marigot Bay, a private lunch on Tintamarre and a dinner in Grand Case fit without rushing. This journey starts from US$4,200 per traveler, and December through April brings the driest weather.
The Caribbean
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