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.