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 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.

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...

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.