Adventures in Boating: The Greater Antilles

Forming the backbone of the Caribbean, the Greater Antilles are a subregion of the West Indies. They include the main islands of Cuba, Jamaica, Hispaniola (which includes Haiti and the Dominican Republic) and Puerto Rico. While smaller, the Cayman Islands are also considered part of the Greater Antilles.

These islands, located in the western part of the West Indies, are formed by continental rock formations (rather than the volcanic and coral of islands like the British and U.S. Virgin Islands, Anguilla, Barbados, Montserrat and Martinique in the Lesser Antilles). They’re the largest islands in the Caribbean and offer the stunning scenery of mountains, waterfalls, rainforests and coral reefs.

With turquoise waters, vibrant marine life and centuries of maritime history, boating in the Greater Antilles offers a unique way to experience the islands. Whether sailing, yachting or fishing, the sea remains the best gateway into the heart of the Caribbean.

Keep reading if you’re considering a Bahamas/Cuba loop, embarking on an extended sailing trip from a private boat dock rental or just want to explore new routes.

Cuba 

Home to Havana’s colorful colonial streets and classic cars, Cuba is the largest island in the Caribbean. It’s famous for cigars, salsa music and the scenic Viñales Valley. A paradise for sailors and boaters exploring from marinas and private boat slips for rent, the island has more than 3,500 miles of coastline with some of the Caribbean’s best coral reefs.

The north coast features scattered cays and reefs, while the southern waters around Cienfuegos and Santiago de Cuba offer historic harbors. Marina Hemingway near Havana is a hub for international yachts, while Jardines de la Reina is famed for pristine reefs and excellent diving.

Hispaniola

The island of Hispaniola is home to the Dominican Republic on the east and Haiti on the west. The nations offer a shared heritage of resilience, cultural richness and incredible mountains and coastal scenery.

The Dominican Republic offers well-developed marinas, particularly along the north coast in Puerto Plata and the east in Punta Cana. The Samana Peninsula is a gem for boaters, especially during whale season.

Though less developed for modern yachting and private boat lifts for rent, Haiti’s southern coast near Jacmel and Île-à-Vache offers raw beauty and a glimpse into authentic island life.

Jamaica 

Jamaica is well-known as the birthplace of reggae, ska, dancehall and iconic musician Bob Marley. The Blue Mountains offer world-renowned coffee and lush hiking trails. You’ll also find the nation's famous jerk cuisine, laid-back vibes and the motto “Out of Many, One People” to be major influences.

The vibrant coastal towns and relaxed cruising waters of Montego Bay, Ocho Rios and Port Antonio are popular stops for boaters. Sailors enjoy fishing offshore for mahi-mahi and marlin, checking out lighthouses or diving beneath the surface. Anchoring near Negril is an excellent way to soak up the island’s legendary sunsets.

Puerto Rico 

With a blend of Spanish, Taino, African and U.S. influences, Puerto Rico is a cultural crossroads known for salsa, reggaetón and flavor-filled dishes like mofongo. San Juan’s old forts and cobblestone streets contrast with El Yunque’s rainforest and natural attractions. 

San Juan’s marina scene is lively, while the offshore islands of Vieques and Culebra offer secluded beaches and anchorages. Puerto Rico is not only a prime boating destination itself, but it’s also a launchpad to nearby islands like the British and U.S. Virgin Islands. If you’re interested in island-hopping from marinas and private boat lift rentals, Puerto Rico is a great choice.

Why Boaters Love the Greater Antilles

• Diverse Experiences: From Havana’s harbor to Jamaica’s reggae-filled marinas, every port has its own flavor.
• Fishing and Diving: World-class sportfishing, coral reef diving and opportunities for fresh seafood straight from the sea.
• Cultural Richness: Each island has distinct languages, music and cuisines, which makes every stop and port of call unique.

Practical Boating Tips for the Greater Antilles

• Best Season: November to May offers steady trade winds and calmer seas. The primary hurricane season is from June 1 to November 30, with the peak period being between August and October.
• Navigation: While marinas are modern in Cuba, Puerto Rico and the DR, Haiti requires more independent anchoring.
• Customs and Entry: Each island has specific requirements, so advance planning is key for smooth sailing.