The Leeward Islands lie to the South and East of the Virgin Islands, spanning some 200 miles and include some 10 major islands operating as different nations. St Maarten, St Martin, St Barts, Saba, St Kitts, Anguilla and Antigua are the most easily recognized names. The distances between the islands are such that many involve open water crossings that are mostly day-long sails in sometimes fairly rough conditions. Thus, the Leeward Islands are ideally suited for those who have hearty sailing experience and love to sail. The rewards are many - experiencing a group of stunningly beautiful islands as varied in topography and culture as they are politically and historically.

Chris Doyle, author of the Cruising Guide to the Leeward Islands categorizes the group of Leeward Islands into three separate categories: The Renaissance Islands including Anguilla, St Martin and St. Barts. The Islands That Brush The Clouds including Saba, Statia, St Kitts & Nevis and Montserrat. The Islands Of Mangroves And Mountains including Antigua & Barbuda, Guadeloupe with The Saintes & Marie Gallante, and Dominica.