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.

• St Martin – Famously half French and half Dutch. The French side is cosmopolitan and stylish, with patisseries, markets, and a European café culture. The Dutch side has a lively marina scene, casinos, and excellent provisioning. Together they make an ideal start and finish point for your charter.
• St Barts – Chic and glamorous with French-style sophistication. Gustavia is lined with luxury boutiques and fine dining spots, while the surrounding bays are perfect for dropping anchor and snorkelling. Think Riviera elegance with a Caribbean twist.
• Anguilla – The opposite of bustle, Anguilla is peaceful and understated. Its long white-sand beaches and tucked-away anchorages offer some of the best swimming and snorkelling in the region. It’s a place to unwind in true Caribbean style.
• St Kitts & Nevis – These twin volcanic islands are rich in natural greenery and history. Explore Brimstone Hill Fortress, wander former sugar plantations, or hike rainforest trails up to volcanic peaks. Nevis in particular exudes relaxed charm and authenticity.
• Saba – Known as the “Unspoilt Queen of the Caribbean,” Saba is unlike anywhere else. Its dramatic, steep cliffs rise straight out of the sea, making it a paradise for divers and hikers alike. Ashore, a single winding road links charming villages with red-roofed cottages. Offshore, Saba Marine Park is renowned for world-class diving, with pinnacles and underwater lava formations teeming with marine life.
• Sint Eustatius (Statia) – A small island with big historical significance. Once a bustling trade hub in the 18th century, Statia still shows traces of its past through old forts and ruins. Today it’s quiet and welcoming, with excellent diving on shipwrecks and coral reefs, plus hikes up The Quill volcano for panoramic views across the Caribbean.

Together, these islands deliver an extraordinary mix: French sophistication, Dutch efficiency, Caribbean warmth, historic intrigue, and raw natural wonder. Few sailing areas allow you to experience such variety so close together. That's what makes this section of the Leeward Islands one of the most rewarding options for a one- or two-week sailing charter.

Related FAQs

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.

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.

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.

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.