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

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.

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. Most charter bases assist with guidance, and crewed charters often handle the process on your behalf.

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.