Sail St Martin, Anguilla, St Kitts & Nevis

Be Spoilt for Choice on a Charter to Remember

This is the place you may have seen on videos from the beach as planes come in just overhead. Once you have touched down, you are on an interesting island that typically of the Caribbean has a complicated colonial history. The southern section (Sint Maarten), is actually part of the Netherlands, while the rest of the island reflects its French rule. As you explore the region under sail, you will hop between these administrations as well as British. But any formalities won't get in the way of a fantastic Caribbean sailboat escape.

Saint-Martin's location provides for a wide range of return-sail itinerary options, from the 7-day charter around the island itself and up to Anguilla, to a longer cruise that takes in any number of nearby destinations. Saint Martin's top sailing spots are in the north and east, which makes it somewhat different from most places in the Caribbean. But there's adequate shelter in places like Anse Marcel and Orient Bay. The waters here, and much of the land, form the Réserve Naturelle de Saint-Martin. This alone is enough to make Saint Martin a worthy choice – to experience some of the world's most diverse warm-water marine diversity in its natural splendour.

Sail the short passage north to Anguilla, and clear at Road Bay on the northern side. Boat racing is Anguilla's national sport, with regular regattas held by locally designed and built boats racing under local rules. The yachting infrastructure is well developed, and there are several beautiful bays to anchor in, particularly around the south western end of the island.

To the south of Saint Martin, Saint Barthélemy (France), St Kitts and Nevis (Britain) and Sint Eustatius (Netherlands) all offer excellent reasons for visiting. St Barts has been labelled the French Riviera of the Caribbean, and it's easy to see why when you call into Gustavia. If that's not what you are looking for, the island has some delightful beaches that are relatively uncrowded, with fine snorkelling conditions.

A leisurely half-day downwind sail takes you to Sint Eustatius, where you clear customs at the southern harbour of Oranjestaad. Popularly known as Statia, this island provides a deferent view of the Caribbean – less developed, less crowded, and with its own distinct topography.

Or sail on by to the sovereign state of St Kitts and Nevis, with its diverse natural landscape. Basseterre is the main center, and just to its south are the best anchorages from which to explore the larger St Kitts. Nevis is a small island with a relatively secluded coastline that can be circumnavigated in a day, with time for short stops along the way.

From Nevis, sail back to base on Saint Martin, or east to Antigua and Barbuda as time, winds and inclination allow. One-way charters from St Martin to Antigua are popular, given the excellent bases in both locations, the convenience of sailing with eased sheats, and all the attractive stopping off points along the way.

This is certainly a fabulous sailing zone, Saint Martin the perfect charter boat hub from which to experience the Caribbean in all its colorful diversity.

Are there any sailing restrictions in the region?

Yes, but they’re mostly straightforward. Marine reserves, particularly in Anguilla and St Barts, may require permits or have anchoring restrictions to protect reef areas. Some areas prohibit fishing or spearfishing. These are usually well-marked on local charts, and your charter company will brief you before departure. It’s all part of helping protect this beautiful sailing region for future generations. Continue reading...

What wildlife and marine life might we see?

This region is home to vibrant marine life. Snorkelling and diving off Anguilla’s reefs and the marine reserve at Colombier in St Barts offer colourful corals, reef fish, and the occasional spotted eagle ray. Sea turtles are commonly seen in bays and around moorings, especially early in the day. During the winter months (January to March), keep an eye out for humpback whales and playful dolphins during open water passages — a special highlight of Caribbean sailing. Continue reading...

Can I provision easily on St Martin before departure?

Yes — provisioning is one of the pleasures of starting your charter in St Martin. Continue reading...

Is this region suitable for less experienced sailors?

Yes, with some caveats. Sailing between St Martin, Anguilla, and St Barts is generally straightforward, with short passages and protected anchorages. Continue reading...

How long do I need for a charter that includes all these islands?

For a leisurely and rewarding sailing itinerary that includes St Martin, Anguilla, St Barts, St Kitts, and Nevis, we recommend setting aside 10 to 14 days. Continue reading...

What are the highlights of exploring St Martin, Anguilla, St Kitts & Nevis by yacht?

Each of these islands brings its own character and charm to your sailing itinerary. Continue reading...

Are there any charter bases other than on St Martin?

Sailing charters in this region generally start and finish on the island of St Martin, where there are multiple well-established bases on both the French and Dutch sides. While Anguilla and St Kitts & Nevis don’t have charter bases of their own, they are easily reached as part of a multi-island itinerary. Continue reading...

What are some highlights on a one-week Caribbean sailing itinerary starting in St Martin?

A typical sailing adventure around St Martin offers a perfect blend of French-Caribbean charm, glamorous nightlife, tranquil anchorages and world-class beaches. Here’s a one-week itinerary covering several island highlights that are all easily reachable on a leisurely sailing schedule. Continue reading...

What sailing conditions should I expect out of Saint Martin?

The prevailing trade winds blow from the northeast to southeast, typically at 15–20 knots, offering great conditions in season for relaxed but exciting sailing. Seas can be moderate with a consistent swell, and line-of-sight navigation makes island-hopping simple. Passages are generally short: for example, St Martin to St Barts is about 15nm and to Anguilla about 12nm, so you’ll never be far from your next anchorage. Continue reading...

What are the entry and customs requirements when sailing between these islands?

Because the Leewards span multiple jurisdictions, you’ll be clearing customs and immigration as you move between islands. St Martin has both a French and Dutch side, each with its own formalities, while St Barts, Anguilla, and St Kitts & Nevis are separate nations. Clearances are usually straightforward but allow time when entering or leaving each territory. Your charter base staff will give guidance, and crewed charters often handle the process on your behalf. Continue reading...

What makes a Leeward Islands charter out of Saint Martin so special?

The sailing grounds centred around Saint Martin offer short, comfortable passages and the unique opportunity to experience several countries in a single week. Each island has its own distinct culture, rhythm, and natural appeal, giving you a wonderfully diverse holiday. Continue reading...

When is the best time to charter a yacht in the Leeward Islands?

The peak sailing season in the Caribbean's Leeward Islands runs from December through April, when the weather is reliably sunny, the trade winds are steady, and the risk of storms is low. Continue reading...

Our client reviews about charter sailing in St Martin, St Barts, Anguilla, St Kitts & Nevis