If you’re a sailor or yachtsman, chances are you already know that it’s not in the cards to “play it safe” and confine yourself to one destination alone.

You wouldn’t want to miss out, especially if you found yourself sailing across the Caribbean Islands. In fact, even if you’re just the kind of person who simply enjoys the random tag-along oceanic voyage, there’s no better region than the Caribbean.

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.

This is even more exciting upon the realization that neither owning a boat or having vast experience in sailing is required to charter a vessel for island hopping.

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.

One of the best benefits of the Caribbean is that you can escape the cold and celebrate your New Year while sailing and swimming!

Although the entire Caribbean is a wondrous sight to behold and your itinerary may vary, here are 6 of the most ideal islands in the Caribbean for sailing a boat or yacht.

The British Virgin Islands

sailing the caribbean

With 25 islands cozily 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 it is the sailing capital of 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.

A few other must-see destinations include the most popular Norman Island Indians and the palm trees and clear blue waters of Jost Van Dyke’s White Bay. With over 100 bars to visit, the British Virgin Islands are frankly a place where you could end up having too much fun.

Activities In the British Virgin Islands:

  • Go snorkeling and windsurfing
  • Grab a drink at the Soggy Dollar Bar (be sure to grab famous “Painkiller”)
  • Take a trip to the Rhone National Marine Park in Road Town
  • Visit Jost Van Dyke’s White Bay
  • Visit Deadman’s Bay at Peter Island
  • Visit the ‘Baths’ at Virgin Gorda Baths


sailing the caribbean

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. In fact, the city of Cienfuegos provides both cabin and bareboat charters for anyone looking to get a more magnificent view of the entire country.

The sparsely visited Jardines de Reina, María la Gorda, and the Isla de la Juventud are the best areas for sailing around Cuba. Sailing to Cuba is like hopping on a time-traveling vessel to a land of old charm and classic American cars dominating the streets.

Activities in Cuba:

  • Visit the Playa Paraiso at the Cayo Largo
  • Visit the Dolphinarium at Cayo Naranjo
  • Swim in the stalagmite-filled Saturno Cave in Varadero
  • Dine on the traditional fare at the Finca Agroecologica El Paraiso in Vinales
  • See the El Nicho Waterfalls in Cienfuegos
  • Visit the Old Havana
  • Diving and snorkeling

St. Vincent and The Grenadines

sailing the caribbean

If you enjoy yachting yet are still in search of that warm ambiance and aesthetic feeling that embodies the entire Caribbean, St. Vincent and the Grenadines is the place to be. With only 9 of the 32 islands hosting inhabitants, St. Vincent and the Grenadines are full of adventure and explorable spots 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 should start their sail in the Windward Islands from the northern side of Bequia then voyage down to the southern region of Carriacou.

Activities in St. Vincent and the Grenadines:

  • Go scuba diving
  • Snorkeling and diving
  • Enjoy the natural scenery (including volcanoes)
  • Take a trip to Montreal Gardens, Vermont Nature Trail and the Bat Cave in St. Vincent
  • Take a trip to the Lagoon Beach in Mustique
  • Dine at the Sugar Reef Cafe in Bequia
  • Sight-see Fort Charlotte in Kingstown

Antigua and Barbuda

sailing the caribbean

Of all the Caribbean Islands, Antigua and Barbuda are 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. Races are incredibly popular here.

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.

Due to its colonial history, infused with local native culture and an opulent, yet naturally beautiful landscape, Antigua and Barbuda have an “old combined with the new” feeling, that offers several options for sailing, shopping, dining, entertainment, history, and sightseeing.

Activities in Antigua and Barbuda:

  • Scuba diving and snorkeling
  • Visit on Antigua Race Week/Sailing Week/Yacht Regatta
  • Explore the local culture in the business district of St. John
  • Visit one of their 365 beaches and coral reefs
  • Dine on local cultural dishes such as their pot stew known as “fungi”


sailing the caribbean

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.

Activities in Grenada:

  • Scuba diving and snorkeling
  • Surfing or riding a water scooter
  • Visit their amazing museums
  • Unwind/relax at one of 7 beaches
  • Visit St. George (Grenada’s capital)
  • Navigate through Grenada’s boat and yacht-friendly accommodating infrastructures
  • Enjoy the local culture and cuisine

Heather Lomax is a contributing writer and media relations specialist for the Privilege Club. Her personal favorite Caribbean destination is Grenada.


It’s been said that one gains a greater understanding of an island from a boat. Being able to assess an island from a boat, then explore what made you stop there, to begin with, is a special moment only sailors and yachtsmen can truly understand.

There are countless secret hideaways and hidden beaches scattered throughout the Caribbean only accessible by boat. 

Wanna celebrate your New Year there? Click here or fill out the form below!

Remember: respect marine life and Keep the Seas Clean!

We wish you fair winds