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Best Sailing Destinations in the Caribbean


If there’s a favorite sailing spot in the whole world, it’d have to be the Caribbean, which attracts millions of visitors yearly because of its slew of charming islands. The experience of seeing an island from a distance, sailing towards it, and then reaching land and exploring it is unparalleled. On top of that, you don’t have to stick with only one island—sailing gives you the freedom to go island-hopping! From examining  the safest Caribbean islands to the most stunning, we’ve done our research to bring you the sailing destinations that will give you the best all-around experience:   


Aruba is the Western Caribbean’s most well-known island. Fast-paced and trendy, it draws in the younger crowd with its nightlife, casinos, and hotels. The capital Oranjestad, which is thrumming with Dutch culture, features colorful colonial buildings, and it’s customary to stay up late and explore the city on foot. On the other hand, Aruba can lay claim to plenty of beautiful white-sand beaches. Given the consistently sunny weather and clear, vivid waters, It’s a veritable tropical paradise. Swimming isn’t as advisable, though, because some of these beaches can be rocky. Instead, kiteboarding, windsurfing, and sailing are more common, thanks to steady, continuous trade winds. Once you’re in the ocean, you’ll be treated to a stunning view of the coastline, and the sunsets are magnificent.



The Bahamas are only 50 miles away from Florida, which is why it’s said to be the Americans’ go-to for island vacations! All in all, it’s a top sailing destination that boasts around 700 islands. Most of these aren’t inhabited, but those that are offer comfortable amenities to travelers, including picturesque resorts and shopping boutiques. Residents here are naturally savvy with sailing, since there are no bridges connecting the islands and they have to ride boats to move around. The shallow, protected waters are friendly for first-time sailors, who find much to appreciate even in the journey as they revel in the clean turquoise waters and rich marine life.  

British Virgin Islands

It’s hard to pinpoint any one location as the world’s sailing capital, but the British Virgin Islands are a top candidate. Sailing is convenient because of strong infrastructure, and trade winds are consistent and mild. On top of that, you won’t have to wait too long because all 25 islands are only a short distance away from each other. Island-hopping is the norm, and sailors and yachters get to experience several scenic beaches while staying at plush resorts. Aside from the surf and sand, it’s also home to serene caves, more than 100 bars, and a geological wonder called Gorda Baths. Tortola, the largest island, is a must to have in your itinerary. 


St. Vincent and the Grenadines

St. Vincent and the Grenadines consists of the main island St. Vincent and two-thirds of the Grenadines, which refer to a larger group of islands. Idyllic and full of natural beauty, it’s an explorer’s haven. Only 9 of the 32 islands are inhabited, and the rest promises adventures that’ll keep your excitement high as you go from one island to the next. St. Vincent even has a tropical rainforest alongside its coral reefs and beaches, while the Grenadines, is rich with wildlife and mountains. Reaching many of the remote islands is impossible through airplane, so boating is the main method of transportation. Although the waters are gentle and the trade winds mild, it’s best for experienced sailors.  

St. Lucia

St. Lucia has been dubbed “Helen of the West Indies” because of how scenic it is. With a total of 7,000 islands, there’s tremendous variety in what to see and experience, from rugged beaches to high-end, luxurious areas. The best view of the Caribbean is said to be found at its southwest corner, which has captivated photographers from all over the world. Despite this, it remains a hidden gem compared to other, more crowded Caribbean islands. The Pitons are an impressive landmark, consisting of stark twin mountains with a height of 2,000 feet, and the unspoiled rainforests bloom with orchids and birds of paradise. Navigation is simple on the waters, which are conducive for sailing to your heart’s content.  


Antigua and Barbuda 

Over at the Eastern part of the Caribbean, sister islands Antigua and Barbuda are hotspots for sailing. Their nickname is the “Land of 365 Beaches,” in reference to their crystal-clear beaches amounting to countless harbors and long stretches of coastline. It holds the Caribbean’s most prestigious sailing week and the Yacht Regatta, which consists of at least six days of races. These are grand events that are open to boats of all sizes, from bareboats to luxury yachts. The top yacht haven in the world, Falmouth Harbor, is also found here! Whatever your level of experience in sailing, these two islands are not to be missed.

There are so many breathtaking islands to visit in the Caribbean. The beauty of it is that no matter how many times you come back, there’s always something new to discover! Each island has its own scenery, culture, and traveler haunts, and with sailing, you decide where your next adventure will be.  



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