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

Day 1: St Martin – Provisioning and a Taste of French Caribbean Life
Arrive in St Martin and spend time exploring the French side’s Marigot Market or Dutch-side Simpson Bay. Provision your yacht, enjoy a waterside lunch, and prepare for a relaxed first night aboard. This is the time to get acquainted with your boat, and your crew if skippered or crewed.

Day 2: St Martin to St Barts – Sophistication and Serenity
A short sail brings you to chic Gustavia, capital of St Barts. Go ashore for designer boutiques, elegant cafes and a buzzing marina scene. For a quieter experience, anchor near Colombier Beach which is popular for snorkelling and swimming, and have an overnight stay in calm waters.

Day 3: St Barts to Anguilla – White Sand Beaches and Solitude
Head to Anguilla for laid-back island vibes. Drop anchor off stunning Shoal Bay or explore the remote Prickly Pear Cays for an off-the-grid feel. Anguilla’s coastline offers ample opportunity for beach walks and snorkelling.

Day 4: Anguilla to St Kitts – Lush Volcanic Backdrop
A longer passage takes you to St Kitts, which provides a contrast with its dramatic, mountainous landscape. Visit the UNESCO-listed Brimstone Hill Fortress or explore the island's botanical gardens and plantation houses. Nevis is just a short hop away if you prefer a quieter anchorage.

Day 5: Nevis – Colonial Charm and Hot Springs
Spend the day around Nevis for a glimpse of Caribbean life untouched by mass tourism. Wander through Charlestown’s colonial streets, relax in thermal hot springs, or hike to enjoy the native flora and fauna. Anchor off Pinney’s Beach for a memorable sunset.

Day 6: Return North via Tintamarre or Pinel Island – Lagoon Calm and Turtles
Sail back toward St Martin with a stop at Tintamarre or Pinel Island. These small islets offer gentle lagoons perfect for paddleboarding, snorkelling, or a beach picnic. Tintamarre is a marine reserve, often visited by sea turtles and rays.

Day 7: Back to Base in St Martin – Wrap-Up and Relaxation
Return to your base marina in time for a final evening dinner ashore. Share stories of the week’s highlights and enjoy the last Caribbean sunset from deck or dock.

Marinas are available in Gustavia (St Barts), Marigot (St Martin), and Nevis, while anchoring is free in many places. Customs and clearance fees are payable when moving between islands.For provisioning we suggest stock up in St Martin’s well-equipped supermarkets, and dine ashore at least once at a local restaurant.

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 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.

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...