St Martin and Anguilla sit just a few miles apart in the northern Leeward Islands, yet they could hardly be more different. St Martin is lively, half French and half Dutch, with some of the best restaurants in the Caribbean. Anguilla is low, quiet and ringed by long, empty beaches. Together, with St Barths a short passage away, they make one of the easiest and most varied crewed charter areas in the region.

Why Charter from St Martin

Princess Juliana International Airport on the Dutch side has direct flights from Europe and North America, so many guests can step off a long-haul flight and be on board the same day. The marinas around Simpson Bay and Marigot are a busy base for crewed yachts, from catamarans to large motor yachts, which gives you a good choice of boats for the winter season.

St Martin Highlights

• Grand Case: a small seafront village on the French side, famous for its restaurants. Dinner ashore here is a highlight for many guests.
• Marigot: the French capital, with a market, cafés and boutiques.
• Îlet Pinel and Orient Bay: calm water, beach restaurants and easy snorkelling on the east coast.
• Tintamarre: an uninhabited island within a nature reserve, with a quiet beach and turtles in the surrounding water.

Anguilla: Beaches and Barely Anyone Else

Just across the channel from St Martin, Anguilla is known for some of the finest sand in the Caribbean. Road Bay at Sandy Ground is the usual first stop, with tiny Sandy Island close by for swimming and lunch. Further out, the Prickly Pear Cays offer clear water and a real sense of seclusion, while Shoal Bay, Meads Bay and Rendezvous Bay are long, pale beaches backed by relaxed restaurants and boutique hotels.

Adding St Barths

St Barths lies a short passage south-east of St Martin, which makes it easy to combine all three islands in a week: Anguilla for beaches, St Martin for food and St Barths for glamour. It is a particularly popular plan over New Year, when Gustavia is at its liveliest. Read our St Barths yacht charter guide for more.

A Sample Week

A relaxed seven nights might look like this. Every itinerary is shaped around your group and the weather, so treat this as a starting point.

1. Board in Simpson Bay or Marigot and settle in at anchor.
2. Cross to Anguilla: Road Bay and an afternoon on Sandy Island.
3. The Prickly Pear Cays for snorkelling and a quiet night.
4. Back to St Martin’s east coast: Îlet Pinel and Tintamarre.
5. Sail to St Barths: Colombier Bay, then Gustavia.
6. A day on St Barths’ beaches and dinner ashore.
7. Return to St Martin, with a final evening in Grand Case.

When to Go

The season runs from December to April, outside the hurricane season. Christmas and New Year are the busiest and most expensive weeks, so book early if you want them; our guide to Christmas and New Year charters explains how festive minimum stays work. February and March bring steady trade winds and more choice, and early March sees the St Maarten Heineken Regatta, a lively week on the island. See our Caribbean season guide for more on timing.

What It Costs

Many crewed catamarans in the area are quoted all-inclusive, while larger motor yachts are usually quoted plus expenses with an Advance Provisioning Allowance (APA). Our guide to yacht charter costs, APA and tips sets out how it works.