Caribbean Sailing Vacations by Ed Hamilton

Cruise The Leeward Islands on your own private charter yacht.
There's no better way to see these beautiful islands

Anguilla, St. Martin / St. Maarten, St. Barts / St. Barthelemy, Saba, Statia / St. Eustatius, St. Kitts / St. Christopher, Nevis, Montserrat, Antigua, Barbuda, Guadeloupe, The Saints / Iles des Saintes, Dominica

Most charterers sail around St. Martin (half Dutch, half French), visiting Anguilla (British) and St. Barts (French). The cruising ground is about the same size as The British Virgin Islands (B.V.I.), with fewer anchorages but fewer boats to fill them.

From sleepy beaches on Anguilla to the fine restaurants and French boutiques on St. Barts, there is something for everyone and a true feeling of being abroad. Sailing conditions are more exposed than The V.I., particularly on the eastern shore of St.
Martin, but distances are short. More adventurous sailors can include the rest of The Leeward Islands (Statia, St. Kitts, Nevis) which are less affected by tourism, but have more exposed anchorages.

You can start your charter in Antigua sailing one way through the Leewards to St. Martin (best this way rather than north to south). From Antigua or Guadeloupe you can also explore the French West Indies and the beautiful Isles de Saintes.
Please give me details of suitable yachts.

Email us

Guidelines for arranging a Leeward Island charter - what to ask:


What type of yacht should I charter? When sailing around St. Martin, the sails between islands are short (the longest is around 2 hours, out to St. Barts) but the seas can be rougher, particularly on the eastern side. This is a popular area for both bareboats and crewed yachts. Bareboat requirements are slightly higher than in the more sheltered Virgins - if you feel your experience is marginal, consider taking a crewed boat. There are virtually no bareboat powerboats due to the seas, but most of the large megayachts in The Caribbean are based in St.Martin.
The differences between a bareboat and crewed yacht charter.

Where should I start and finish my charter? The bareboat companies are based in St. Martin and Antigua. It is sometimes possible to charter one way. Charters out of Antigua normally cruise around the island and out to Barbuda as the other islands are a full day's sail away. Crewed charters can start, finish and cruise virtually anywhere in the Leeward chain.

What does it cost? Prices for a 7 day crewed charter start around $1200 per person for a party of 4 (see sample). A more luxurious yacht around 60-70 feet will average $2500 - $3000 per person (see sample). Per person prices will be lower for parties of 6 or 8 (see sample).

How do I book? All boats look great on the internet, so it is important to use a broker who knows the boats and crews personally and can give you unbiased advice. The crew is generally more important than the boat, particularly on smaller charters. A good broker will ensure your money is kept in an escrow account rather than given to the boat, and can make sure you use the correct contracts etc.. We have 33 years experience in arranging charters and are based right in beautiful Wiscasset, on the Maine Coast. The next stage is to tell us what you are looking for so that we can send you a selection of yachts that fit your requirements.