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Best Sailing Vacations in the Caribbean

Whether you’re taking your first sailing course or have years of nautical miles under your belt, the Caribbean has some of the top sailing spots in the world. From the calm waters of the Virgin Islands to the more challenging open sea in the Southern Caribbean, taking a sailing vacation in the Caribbean is in a class of its own. 

Greater Antilles 

The Greater Antilles features many popular vacation destinations that visitors cruise and fly to. But did you know that islands like Puerto Rico and Jamaica are also home to some of the best sailing locations in the Caribbean? 

Here are some top spots to sail in the Greater Antilles.

Puerto Rico

Nestled between the Atlantic and the Caribbean, Puerto Rico has some incredible sailing spots. Winds are a bit stronger here than in the US Virgin Islands, but it’s not uncommon to enjoy breezes around 15 knots during peak season. 

If you plan to visit Puerto Rico, some of the best sailing spots include: 

  • Spanish Virgin Islands: Though also considered part of the Virgin Islands, the SVI are part of Puerto Rico. Visit Vieques and Culebra for remote beaches and nature trails ideal for the most adventurous sailors.
  • San Juan Bay: Travelers who want an urban sailing vacation can stick to San Juan Bay near the capital of Puerto Rico. Pulling up to the historic colonial town, you can see sites like the Castillo San Felipe del Morro from the sea.

JamaicaFour people enjoying a sunny day on a sailboat in the Caribbean.

If you want to sail around Jamaica, you’re in luck. Some of the top sailing locations in the world are just off the shores of this small but legendary Caribbean Island. 

You’ll find the best sailing in Jamaica on:

  • The North Coast: Port Antonio is a scenic village with waters that are often perfect for sailing. From the sea, you’ll notice homes dotting the tree-lined hillside, a lighthouse, and clearer blue waters. Other top sailing spots include Ochos Rios and Montego Bay.
  • South Coast: Port Morant is a popular place to sail on the southern side of Jamaica. It’s a small town with less traffic than the more famous sailing destinations up north.

Lesser Antilles

It’s easier to island hop and check out the many sights, sounds, and flavors of the Lesser Antilles on a sailing vacation. 

Virgin Islands

Sailing the Virgin Islands offers a treasure trove of natural beauty, endless sunshine, and near-perfect sailing conditions for many months of the year. Whether you choose an itinerary in the BVI or USVI, the Virgin Islands have some of the best sailing destinations in the world.

These include: 

  • Virgin Gorda: Towering boulders, volcanic caves, and tropical fish in every color of the rainbow await at the most popular sailing destination in the BVI.
  • St. John: 60 percent of this USVI is dedicated to national parks, with forests, beaches, and coral reefs galore. 
  • Anegada Horseshoe Reef: If you take advanced classes with Go Sail VI, you may have the opportunity to visit one of the top sailing locations in the Caribbean. This dive spot features 18 miles of barrier coral reef and the sea creatures who call it home.

Antigua & Barbuda

Another favorite location for a sailing vacation in the Caribbean is Antigua & Barbuda. The island is full of historic harbors, crystal clear waters, and a beach for every day of the year. 

Some of the top sailing spots in Antigua are:

  • Jolly Harbour: This thriving marina has excellent sailing conditions and is home to restaurants, stores, and accommodations on land.
  • Carlisle Bay: This idyllic stretch on the southwestern tip of Antigua has ideal sailing conditions and beautiful scenery with palm trees and soft golden sands.

Sail the Caribbean 

Join us on a sailing course through the US Virgin Islands or the British Virgin Islands to experience some of the top sailing spots in the Caribbean. 

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