The Caribbean’s most underrated charter base — and one of the most rewarding once you know these waters
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Why St Martin is one of the most rewarding bareboat bases in the Caribbean
One of the biggest advantages of sailing from St Martin is how much you can realistically cover without needing long offshore passages between islands.
Anguilla, St Barths, Tintamarre, Pinel, and the northern coast of Saint-Martin itself all sit within relatively manageable sailing distances, which allows itineraries to stay flexible throughout the week depending on weather and crew experience.
The island also has some of the best sailing infrastructure in the northeastern Caribbean.
Most charter activity centers around Simpson Bay Lagoon on the Dutch side and the marinas of Marigot or Anse Marcel on the French side. Fuel, provisioning, marine services, technical support, customs facilities, and haul-out infrastructure are all easy to access compared to many smaller Caribbean islands.
Winter conditions are generally what attract most sailors here. From December through April, the northeast trade winds typically create reliable sailing conditions across the northern islands, while still allowing relatively protected cruising along parts of the leeward coast depending on swell direction and weather patterns.
And unlike some Caribbean charter destinations where the sailing becomes secondary to staying at anchor, St Martin still feels built around moving between islands.
Most days naturally become a mix of actual sailing, swimming stops, marina evenings, customs clearances, beach lunches, and short passages that keep the trip feeling active without becoming exhausting.
Where you can sail from St Martin - St Maarten
This is where St Martin starts becoming addictive for sailors.
Everything sits relatively close together, but nothing feels repetitive. The islands change constantly around you — different colors, different coastlines, different atmospheres — without forcing long overnight passages between stops.
From Simpson Bay or Marigot, you can build an entire week around short, satisfying sails that still feel like genuine island-hopping.
Anguilla
Only a few hours north of St Martin, but the atmosphere changes almost immediately once you arrive.
The coastline flattens out, the water turns impossibly clear on the leeward side, and everything starts feeling quieter, slower, more spread out. Sandy Ground remains the main clearance port for private vessels, and once formalities are done, the island opens into long white beaches, calm anchorages, and some of the clearest water anywhere in this part of the Caribbean.
Anguilla feels less built for tourism and more built for simply disappearing for a while.
St Barths
The sail into Gustavia is one of those arrivals people remember long after the trip ends.
You round the coastline, the red roofs begin appearing above the harbor, megayachts sit quietly at anchor, and suddenly the whole atmosphere shifts into something more polished and distinctly French-Caribbean.
St Barths requires a bit more planning — especially during high season when moorings and anchorage space become limited — but it’s still entirely realistic as part of a St Martin charter itinerary. Leave early, watch the weather window, and the crossing becomes one of the highlights of the week.
Tintamarre Island
Tintamarre sits just off the French side, protected inside the nature reserve, and somehow still feels surprisingly remote considering how close it is to St Martin.
Most boats come here for the water.
Sea turtles glide through the anchorage, the snorkeling is excellent in calm conditions, and the island itself remains completely undeveloped. It’s the kind of stop where nobody really wants to leave early once lunch turns into swimming, then swimming turns into another hour drifting quietly off the boat.
Pinel Island
Pinel is less about sailing and more about slowing the day down.
The anchorage sits inside the protected waters of Cul-de-Sac on the French side, making it a favorite lunch stop for both locals and charter boats. The water stays shallow and bright turquoise, dinghies move constantly between the beach restaurants and anchored boats, and afternoons here tend to disappear very quickly.
Not really an overnight stop — but absolutely part of the classic northern St Martin sailing rhythm.
The leeward coast of St Martin
One of the underrated parts of chartering here is that even the main island itself gives you several genuinely enjoyable stops under sail.
Grand Case, Marigot, Anse Marcel, Friar’s Bay… each bay feels slightly different depending on the swell, the wind, and the time of day. Some nights feel calm and almost sleepy. Others end with dinners ashore, music drifting across the anchorage, and dinghy rides back to the boat well after dark.
Grand Case especially works beautifully during a charter week. Few things feel more Caribbean than finishing a day under sail, showering off the saltwater, then walking straight into one of the best restaurant villages in the region.
The two sides of the island — and why it matters for your charter
⛵ Start your search on Sailo — bareboat, captained, and crewed charters in St Martin
→ Browse all boats — French side (61 available) →
→ Browse all boats — Dutch side (22 available) →
✅ Free cancellation on most listings | Secure booking via Sailo
Bareboat vs captained charter — which one is right for you
If you already sail regularly, the difference probably needs little explanation. But St Martin attracts a mix of experienced skippers, occasional sailors, and travelers who simply want to experience the Caribbean from the water — so it’s worth understanding how charter options usually work here.
Bareboat charter
A bareboat charter means the boat is entirely yours for the duration of the trip.
You handle navigation, anchoring, passages, customs formalities between islands, weather decisions, and everything that comes with managing the boat underway. Most charter companies will ask for a sailing résumé, previous charter experience, and sometimes certifications such as ASA or RYA credentials before approving a bareboat rental.
This option gives the most freedom.
You choose your pace, your route, your anchorages, and how the days unfold once you leave the marina. For experienced sailors, that independence is exactly the point.
Crewed or captained charter
A crewed charter includes a professional skipper — and sometimes additional crew depending on the boat.
In practice, this completely changes the rhythm of the trip.
Instead of focusing on navigation, moorings, weather windows, or customs procedures, you spend more time actually enjoying the islands themselves. Long lunches ashore, swimming stops, sunset sails, beach restaurants, relaxed mornings at anchor… the experience becomes less technical and much more centered around the destination.
For travelers without strong sailing experience, or groups mixing sailors and non-sailors together, this is often the more comfortable option.
The flexible middle ground
One thing that works particularly well in St Martin is that many charter boats offer both possibilities.
A lot of listings allow you to book the boat bareboat-style or add a captain during checkout depending on your experience level and the kind of trip you want to have. That flexibility makes St Martin a surprisingly accessible charter destination even for people who don’t necessarily want the responsibility of managing a boat themselves every day.
🚗 Getting to your charter base — most pickup points are near Princess Juliana Airport (SXM). A rental car makes provisioning and marina transfers significantly easier.
→ Compare car rental rates at SXM airport →
How to book your yacht charter through Sailo
Sailo works as a marketplace connecting travelers directly with local boat owners, captains, and charter companies around St Martin and the northern Caribbean.
The booking process itself is fairly simple. You enter your travel dates, choose a departure area, browse the available boats, and decide whether you want a bareboat rental or a charter with captain included. Some boats can be booked instantly, while others require confirmation from the owner or operator before the reservation is finalized.
You’ll also notice that departure points change the rhythm of the trip quite a bit. French-side departures often place you closer to the northern anchorages and nature reserve areas, while Dutch-side charters tend to offer easier airport access and more marina infrastructure around Simpson Bay Lagoon.
Pricing depends heavily on season, boat size, and whether crew is included. From December through April — especially around Christmas, New Year’s, and spring break weeks — the better-rated boats usually book much earlier than people expect.
Before confirming a reservation, it’s worth reading the listing details carefully. Fuel policies, security deposits, captain fees, cancellation terms, and onboard equipment can vary significantly between operators.
⛵ Start your search on Sailo — bareboat, captained, and crewed charters in St Martin
→ Browse all boats — French side (61 available) →
→ Browse all boats — Dutch side (22 available) →
✅ Free cancellation on most listings | Secure booking via Sailo
FAQ – Bareboat rental in St Martin
Do I need a sailing license to rent a bareboat in St Martin?
Yes. Most charter companies require a recognized offshore sailing certificate — ASA 104, RYA Day Skipper, or equivalent — plus a logbook showing relevant offshore experience. Some operators conduct a checkout sail before releasing the vessel. Captained charters have no license requirement.
What is the best time of year for a sailing charter in St Martin?
December through April is peak season: trade winds are steady (15–20 knots northeast), seas are manageable, and the weather is dry. February and March offer the most consistent conditions. Summer months bring lighter winds and increased hurricane risk from July through October — most operators suspend bareboat charters during this period.
Can I sail to Anguilla and St Barths from St Martin?
Yes to both. Anguilla is eight miles north — a short hop with straightforward customs clearance at Sandy Ground. St Barths is 22 miles southeast; allow a full day and arrive early at Gustavia to secure an anchorage. Both are standard stops on a St Martin charter itinerary.
What is the difference between a bareboat and a captained charter?
A bareboat charter means you rent the vessel without crew — you are the skipper. A captained charter includes a professional skipper who handles navigation and boat management. Many Sailo listings on St Martin offer captain as an optional add-on, letting you decide at booking.
Where do most charter boats depart from in St Martin?
The main bases are Simpson Bay Marina (Dutch side) — the largest marina in the Caribbean — and Marigot or Anse Marcel (French side). Oyster Pond on the eastern coast is used by some operators for its proximity to both the Atlantic and leeward passages.
How far in advance should I book a charter in St Martin?
For high season (mid-December through April), booking 4–6 months in advance is strongly recommended. Popular bareboat slots and fully crewed catamarans fill early. Shoulder season (May, November) can be booked 4–8 weeks out with more flexibility.
Is St Martin a good base for first-time charter sailors?
For first-time bareboat sailors, St Martin can be challenging — the passages to Anguilla and St Barths involve open water and require navigational confidence. A captained or crewed charter is a better introduction: you gain local knowledge of the anchorages, conditions, and island stops without carrying full responsibility for the vessel.
What does a typical week-long charter cost in St Martin?
Bareboat rates for a 44–46ft catamaran run approximately €6,500–€9,000 per week in high season. Captained charters with crew add 30–50% to that figure. Day charters on a crewed catamaran average around €1,100–€1,800 per half-day. Fuel, provisioning, marina fees, and customs charges are additional.
⛵ More sailing and boating on St Martin:
→ Boat tours departing from the French side →
→ Catamaran tours in St Maarten →
