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. 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.

Is this part of the Caribbean suitable for families or first-time charterers?

Yes. With short passages, safe anchorages and a wide choice of beaches and activities, the Leewards are family-friendly and ideal if new to chartering. Catamarans are popular with families thanks to their space and stability. A skippered charter is a good choice for less experienced groups who want more peace of mind. 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. Most charter bases assist with 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. This is also when the islands are at their most vibrant, with bustling harbours and lively shore activities. From May to June you’ll find calmer seas, fewer crowds, and lower prices, though there may be occasional showers. July to October falls within the hurricane season, and while charters still operate, this period is best suited to experienced sailors and those seeking good deals with flexibility. Continue reading...

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