The Leeward Islands
The Leewards include: St. Maarten/St. Martin, Anguilla, St. Barts, St. Kitts, Nevis, Antigua, Barbuda, Guadeloupe and Dominica. Montserrat is also a part of the region but recent persistent volcanic activity make it a poor choice for a charter holiday at the moment.
A popular off-the-wind option is sailing from Antigua to St. Martin including St.Kitts, Nevis and St.Barts along the way.
Similar to the Virgin Islands, the winds are generally NE to SE at 15-25Kts..higher during the "Christmas Winds" period ( Dec.-Mar.)
Antigua
With more anchorages than any other Caribbean island, and 365 beaches, it's not surprising that Antigua gave birth to the yacht charter industry. Home of the now famous Antigua Race Week and Classic Yacht Regatta. Falmouth Harbour has excellent dockage facilities at the Antigua Yacht Club marina, Falmouth Marina and Catamaran Club Marina. Nearby, the English Harbour Dockyard is steeped in history. There are fine marina facilities, good restaurants and it is within reach of lovely beaches and hiking trails.
More info can be found at: www.antigua-barbuda.org
Sint Maarten/Saint Martin
French St. Martin is famous for its restaurants and fabulous beaches - including clothing optional beaches and resorts. Marigot is the heart of the French side and has many wonderful boutiques, restaurants and cafes.
More info can be found at www.st-martin.org
Phillipsburg - Dutch St. Maarten's capitol is a shopper's paradise for clothes , electronics and jewelry. Gambling is legal here and many of the large hotels have casinos.
More info can be found at www.st-maarten.com
Guadeloupe & Dominica
Point-a-Pitre, the main town in Guadeloupe, has great restaurants, shopping and secure marinas. An exploration of Les Saintes and Marie Galante is also recommended.
More info can be found at www.guadeloupe.fr
Dominica is a rugged island with and excellent anchorage in Prince Rupert Bay. From here, hikers and nature lovers will enjoy exploring Fort Shirley or taking a boat trip up the Indian River. Inland adventures include exploring the island's many waterfalls and rainforests.
More info can be found at www.ndcdominica.dm
Find much more information and sample itineraries at Distinctive Yachts