An all-year-round sailing destination

The Caribbean is arguably the best destination for vacation sailing and well-known for its: 

  • gorgeous tropical landscape, 
  • tranquil atmosphere, 
  • beautiful weather, 
  • astonishing beaches, 
  • and vibrant, diverse cultures.

There are plenty of islands in the Caribbean that are quite accommodating to boats and yachts, providing the proper infrastructure, fuel, and other necessary provisions to make your sailing vacation as breezy, easy, and magical as possible. 

The best thing sailing the Caribbean is that they are an all-year-round sailing destination. You can go sailing for your summer vacation or winter holidays. 

Just be careful during the hurricane season that starts in June and lasts till December.


With 25 islands located within the waters of the Sir Francis Drake Channel, the British Virgin Islands are considered by some to be the world’s best sailing location and the capital for sailing the Caribbean

What makes the BVI such a prime location for sailing are the mild winds and short distances between islands. 

Whether you’re bareboat chartering or cabin charting, the BVI makes it easy and fun to island-hop or sail to your preferred island of relaxation.

Famously known for its Caribbean hospitality, the BVI offers some of the most beautiful scenery you’ll lay eyes on.

This is ever so clearly seen through its “baths” at the world-renowned Virgin Gorda Baths, where warm bathing pools are created from rock formations.

sailing the Caribbean

Beautiful tropical beach with palm trees, white sand, turquoise ocean water and blue sky at Tortola, the British Virgin Islands


One of the best (and most unique) countries for sailing, due to its perfect landscape and under-utilized sailing routes, is Cuba.

Located just south of the Florida (Miami) coastal lines, Cuba is a very intriguing place for anyone who visits, full of rich history and culture with stunning architecture to match. 

Its most popular cities include Cienfuegos, Camagüey, Havana, and Trinidad; each city houses similar culture, yet they are unique in their ability to tell their own tailor-fitted stories of mishap and adventure.

Sailing around Cuba can be easily navigated, whether by cabin charter or bareboat. 

The sparsely visited Jardines de Reina, María la Gorda, and the Isla de la Juventud are the best areas for sailing around Cuba. 

sailing the Caribbean

Old classic car on the beach of Cuba

St. Vincent and the Grenadines 

With only 9 of the 32 islands hosting inhabitants, St. Vincent and the Grenadines are full of adventure and spots worth exploring only reachable by boat.

The St. Vincent island holds the most surreal beaches, coral reefs, and tropical rainforest, while The Grenadines boasts its turquoise lagoons and mountainside location, full of plant life, wildlife and most importantly, sea life.

Although the waters are warm and gentle with mild winds, navigating the islands of St.Vincent isn’t for the novice sailor. 

Experienced sailors can start their sail in the Windward Islands from the northern side of Bequia then voyage down to the southern region of Carriacou.

sailing the Caribbean

Tranquil tropical beach on Bequia island in St Vincent and the Grenadines

Antigua and Barbuda

While Sailing the Caribbean Antigua and Barbuda should be the best charter destinations for sailing.

Located in the eastern region of the Caribbean (part of the Leeward Islands), Antigua and Barbuda (Antigua’s sister island) have 365 pristine beaches with more than enough anchorages and harbors to entice sailors to extend their vacation in hopes of visiting each individual island.

Antigua has a history of being one of the best sailing locations, as it features one of the top yacht havens in the world, the Falmouth Harbour.

Aside from having the best harbors, there are plenty of sailing and yacht activities, as Antigua hosts “Sailing Week” each year in April and the Classic Yacht Regatta.

Sailors with boats of all sizes such as bareboat, crewed yachts, catamarans, sailboats and luxury yachts are all welcomed, as Antigua and Barbuda accommodate the casual sailor to the most avid yacht voyager.

With the exception of late August-September, Antigua and Barbuda have the best warm weather for sailing.

sailing the Caribbean

Antigua Bay, view from Shirely Heights, Antigua


In close proximity to St. Vincent, Trinidad and Tobago, and located just south of the Grenadines, Grenada is made up of 3 magnificent islands.

Known for its crystal-clear waters, elegant beaches and coral reefs, Grenada is a great place for anyone looking for pure relaxation and/or water-related activities.

Its early cultural and architectural influences by European and South American settlers can still be seen today within Grenada’s local language and cuisine.

Unlike many of the aforementioned destinations, the weather in Grenada is consistently warm, even though the tropical storm months of August and September.

This allows for year-round sailing. Not to mention, Grenada beckons to sailors as its islands are readily equipped with protected harbors and anchorages for yachts.

In addition to Grenada’s sailing accommodations, the sailing infrastructure itself is highly developed for sailors and yachtsmen to safely and securely navigate throughout the islands.

sailing the Caribbean

Turquoise sea and anchored yachts at Sandy beach island, near Carriacou island, Grenada

Interested in sailing the Caribbean? Tell us more about it by filling out the form and start your sailing vacation.