Sailing in Leeward Islands is both fun and sundry because the region is composed of several stunning places. These are are the islands of Dominica, Saint Bartholomew, Anguilla, the American Virgin Islands, the British Virgin Islands, Montserrat, St. Kitts and Nevis, Antigua and Barbuda, St. Martin, Saba, St. Eustatius, and Guadeloupe. Although it is not officially recognized as part of the group, the Isla Aves has been informally included as one of the Leewards. The British part of Leeward Islands once have a colonial flag. It was officially used from 1871 to 1956. However, the formal use of the flag was discontinued when the colony of the Leeward Islands was ended in 1956.

The name "Leeward" was given to the group of islands because of the current winds in the area that blows from northwest. These trade winds are almost constant all over the year and blows from 10 to 25 knots. Because of the Atlantic ocean, the strongest currents and largest waves are most often on the northeastern sides of the islands. The waters of the Caribbean Sea are generally much calmer and make easier sailing.

Sailing in Leeward Islands is best done from the months of November to July. This period is recognized as the most perfect yacht season of the year. Also, the months of December to March is recognized as the peak season wherein thousands of local and international sailors all around the world flock the Leewards and sail its magnificent coastal waters. Average air temperatures range from 22º to 30º C (72º to 86º F) and the water temperatures stay between 20º and 23º C (68º and 74º F). July to October is the least attractive months because this is when the hurricane season is very prevalent.

Leeward Islands have been considered as one of the most excellent sailing areas in the world. This is true especially along the areas of St. Martin, Antigua, and Dominica. At present, you will notice a lot of big cruises such as luxury motor yachts and Super Yachts while cruising in the Lewards.

One of the best starting points when cruising in Lewards is in Antigua. This islet is a major yacht hub not only in the Lewards but also in the Caribbean. Antigua became famous when it became Great Britain's base in the West Indies during the 18th century. Antigua has remarkable beaches with beautiful white sand.

From Antigua, you can turn your route to St. Kitts and Nevis - one of Caribbean's several "twin island nations". Sailing in Leeward Islands through the St. Kitts and Nevis, your itinerary can be filled with adventure and fun. The place is beautiful and its waters so magical. It is also very historic as evidenced by its old sugar plantations, forts, and monuments.