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Sailing through the heart of the Caribbean, the Antilles is an enchanting archipelago that has captivated seafarers for centuries. BoatPlanner takes you on a virtual trip in the Antilles from the Columbus era to our days to showcase this remarkable sailing destination.

The Antilles span across the Caribbean Sea, forming a bridge to the Americas. Together with the Lucayan Archipelago, they form the West Indies. Geographically, they are divided into two main groups of islands; the Greater Antilles on the north, including Cuba, Jamaica, Hispaniola, and Puerto Rico; and the Lesser Antilles, stretched all along a volcanic arc between the Greater Antilles and the continent of South America. The Lesser Antilles are a cluster of islands among which the Leeward Islands and the Windward Islands.

Moorings & Anchorages

The steady trade winds, the calm waters, and an abundance of sheltered anchorages in the Antilles create ideal sailing conditions.

Greater Antilles:

Cuba: Cuba’s most popular spots for anchorage are the Hemingway Marina in Havana, Cayo Largo, and Cienfuegos. Santiago, the second largest city in Cuba is located on a bay connected to the Caribbean Sea and an important seaport.

Jamaica: Montego Bay and Ocho Rios are known for their welcoming anchorages.

Hispaniola: Samana Bay in the Dominican Republic offers secure anchorages, while Labadee in Haiti provides a serene escape with beautiful anchorages.

Puerto Rico: Anchor at San Juan, Culebra, and Vieques to visit the old city and the nearby beaches, engage in dive spots, and taste local delights in restaurants and bars overlooking the ocean.

Lesser Antilles:

The Leeward Islands, including Antigua, St Kitts, and Nevis provide well-protected anchorages and marinas, such as English Harbor in Antigua and Basseterre in St Kitts. In the Windward Islands, locations like St Lucia’s Rodney Bay and Grenada’s Prickly Bay offer safe anchorages for sailors.

Weather & Climate

The Great Antilles enjoy a tropical climate. The dry season spans from November to April, with the highest risk for hurricanes in September. The Lesser Antilles enjoy a tropical climate with trade winds and less risk of hurricanes compared to the Greater Antilles. The dry season extends from December to May.

History & Places of Interest

The Antilles hold a significant place in history, closely tied to the voyages of Christopher Columbus back in 1492, during his conquest expedition to the New World. Once he set foot on this beautiful exotic place, he named it ‘Las Antillas’ in honor of St Ursula.  

Greater Antilles: Discover the historic streets of Old Havana in Cuba, a UNESCO World Heritage site, explore the colonial forts like Morro Castle, and delve into the local music and culture in the streets of Santiago de Cuba. While in Jamaica, you should definitely visit the Bob Marley Museum in Kingston and explore the historic Port Royal. Santo Domingo’s Zona Colonial in Hispaniola is a well-preserved district of colonial architecture marvels. The Citadel Laferriere in Haiti is a UNESCO World Heritage site not to be missed by visitors. In Puerto Rico, wander through the cobblestone streets of Old San Juan, Puerto Rico, visit El Morro and San Cristobal fortresses, and explore the tropical rainforests of El Yunque.

Lesser Antilles: Explore Nelson’s Dockyard in Antigua, Brimstone Hill Fortress in St Kitts, and the colonial architecture of St John’s. Visit the mountainous volcanic plugs and the lava necks of Pitons in St Lucia, the historic Fort George in Grenada, and the Carib Territory in Dominica to get the gist of local natural and historical beauty.


The Greater Antilles boasts a long stretch of white-sanded beaches with turquoise waters, such as the Varadero Beach and Guardalavaca, both in Cuba. Enjoy the emerald waters of Jamaica on Seven Mile Beach in Negril and the Doctor’s Cave Beach, in Montego Bay. Punta Cana in the Dominican Republic and Labadee in Haiti offer picturesque beachfront and water activities on Hispaniola. The famous Flamenco Beach on Culebra Island and Luquillo Beach are but a few of Puerto Rico’s natural treasures.

The Lesser Antilles are renowned for their picturesque shores such as the likes of Jolly Beach in Antigua, South Frigate Bay in St. Kitts, St. Lucia’s Anse Chastanet Beach, and Grenada’s Grande Anse Beach.


Dance, dance, dance: Immerse yourself in local culture. Become one with the Cubans dancing salsa in the streets of Havana. Let reggae sounds vibrate your body on the sunny beaches of Jamaica. Or mingle with the crowd during Antigua’s Carnival and Grenada’s traditional festivals. The welcoming locals in the Dominican Republic will introduce you to the merengue and bachata rhymes, but if you want to see the real thing, visit the Buena Vista Social Club and the Tropicana Cabaret in Havana.

Tobacco tours: Tobacco lovers will get a first-hand experience touring the tobacco farms in Vinales to learn about the history and art of cigar making.

Regattas: The Antilles also host a series of regattas and sailing events, including the Pineapple Cup from Fort Lauderdale to Montego Bay, in Jamaica and Antigua Sailing on Antigua.  Of course, there are several local yacht races and events you can take part in if you feel for it.

Hiking: If hiking is your thing, then climb the famous Dunn’s River Falls in Ocho Rios, the Blue Mountains in Jamaica, the volcanic Pitons in St Lucia, and the lush rainforests in Dominica.

Watersport activities: The crystal-clear waters throughout the Antilles are ideal for watersports, such as snorkeling and diving. Cuba offers some of the best diving sites in the Caribbean. Explore the underwater world at Jardines de la Reina or Maria La Gorda. Dive into the coral reefs of Antigua and Barbuda, where you’ll encounter colorful marine life.