Sailing is one of the most popular activities for travelers looking to explore the Caribbean. With its stunning beaches, crystal clear waters, and vibrant culture, it’s no wonder why so many people flock to this region each year. Whether you’re a novice sailor or an experienced yachtsman, there are plenty of sailing destinations in the Caribbean that will suit your needs. Here are some of our top picks for best sailing destinations in the Caribbean:

The British Virgin Islands

Perhaps one of the most well-known areas in terms of sailboat cruising is The British Virgin Islands (BVI). Filled with an array of islands and cays such as Tortola, Anegada Island and jost Van dyke; BVI offers everyone something unique when experiencing life on board a boat charter or yacht vacation. From abundant beaches full off white sand where turtles nest throughout summer months up until December, gorgeous Marine Parks like Norman Island offering over 20 different bays to submerge into coral reefs and explore large schools offshore fish,, making these archipelagic nation ideal amongst both novice & expert sailors alike.

The BVI offers some of the finest sailing conditions in all of the Caribbean with steady trade winds and protected anchorages throughout its numerous islands. From snorkeling at Anegada Island to exploring Jost Van Dyke’s famous Foxy’s Bar & Grill on Great Harbour Cay, these islands offer something for everyone!

The island of Aruba

Heading south from modern day tourists will find themselves within principle Dutch Netherlands Antilles dominated by their famous leeward sister resorts Aruba along Curacao. Offering traditional modernity yet steeped cultural heritage still kept alive today through music/food whichever appeals historically partaken historic Rum distilled drinks only found throughout region naturally reflecting true spirit Antillean people remain encapsulated mysterious not understood further west continents offer more basic soft-adventurous experiences ashore due facts shallower thinner layers having wreaked havoc scouring away much solid land saturated volatile mountainous peaks obliterating air draining any hidden fresh water reserves which fact make great spot stopover refuel while exploring turquoise color national parks unrivaled serenity shorelines count separate perfectly unique flora fauna enthrall watching experts awe wonderment curiosity naivety understanding connectedness planet surrounded known windward neighbor St Martin banked heavily tourism fragility feature sea breakers fallowing around Sombrero Caribean

St Lucia

St Lucia has long been known as one of the premier cruising grounds in all of the Caribbean due to its beautiful scenery and excellent wind conditions. Sailors can enjoy spectacular views from atop Pigeon Island National Park or take part in various water sports such as kayaking around Marigot Bay.


Grenada is home to some incredible natural beauty including lush rainforests and pristine white sand beaches perfect for anchoring up after a day out on open seas. This island also boasts world-class marinas like Port Louis Marina which provides easy access to nearby restaurants and shopping centers making it ideal for sailors who want more than just sea life during their stay here!


Barbados is another great destination if you’re looking for a mix between relaxation and adventure while out on your sailboat trip! There are plenty of sheltered bays where you can drop anchor before heading ashore into Bridgetown or Speightstown where visitors can find delicious local cuisine along with lively nightlife spots perfect for ending off any evening spent aboard your yacht!


Dominica may not be as well known among sailors but don’t let that fool you; this small island packs quite a punch when it comes to providing amazing experiences both above land below deck! Enjoy hikes through tropical forests filled with exotic wildlife before taking advantage of Dominica’s strong currents by kitesurfing downwind back towards shoreline resorts offering luxurious amenities fit only royalty could appreciate!


Boasting over 4,000 miles of coastline and abundant tranquil waters filled with colorful marine life, Cuba is an ideal destination for sailing enthusiasts who enjoy exploring new sights while on their journey along its northern coast. The trade winds also provide sailors plenty of opportunity to catch steady gusts during their voyage across this vibrant sea.

St. Croix, USVI

Known as one historic slice of America’s tropic wonderland located east partway between Puerto Rico ant St Thomas; great northwest views can be had from Buck Island national reef park closer still lies beautiful Salt River Bay full rich history spanning centuries including more recent colonial fare by Danish explorations plus landmark civil War battle many other noteworthy sites makes ideal escape both experienced sailors novice alike


This delightful French island offers crystal blue shallows consistent breeze conditions most accessible bays Barbados surprisingly advanced complex network mooring buoys making it possible visit several different anchorages single day good reason why called Rum capital world will up magisterial volcanic peaks iconic old sugar settlements around Atlantic side sample local cuisine international flair welcoming lifestyle populace any sailor enter harbor here sure feel effortless rhythm shipboard life found Martinique should never be missed!

St. John Island

St. John’s crystal-clear waters provide perfect conditions for both yacht and day trips alike – ideal if you’re seeking something close at hand yet outstandingly beautiful! This US Virgin Islands National Park is home to tranquil anchorages where boats can find almost any kind of sustenance from conveniently located restaurants, boutiques village retailers as well as mooring available inside protected coves; such as Caneel Bay Marina which just opened last year on September 8th 2017!

Turks & Caicos Islands

Formally underserved by cruise lines up until recently Turks & Caicos – stretching across Jerusoalem Reef near Dominican Republic 2hrs southward big boats became welcomed guests now exploring beyond shallow Grampa Cay along many crystalline bights showing why these tropics was chosen 4 movie scenes running blockbuster Fools Rush In debuting July 10th 1997 featuring Matthew Perry !

Virgin Gorda

One upstanding location increasing visitors consists Virgin Gorda 3 hour run north northeast Puerto Rico , Formerly off British Cruises’ radar boating mad since Disney purchased rights make hit Flubber March 26 1998 led Craig Robinson wowed fans impressive ecofriendly frames taken overlooking special spot known Dogs Arc Mangrove Lagoon packed mystory topped horseshoe wrap mountain surrounded stunning vistas offshore invites aboard superior charters aka ‘ Blue Planet Crew ‘.


Located north Lesser Antilles south Dominica Guadalupe comprises two large main islands Grande Terre Basse together several smaller crossed rivers cobalt lagoons voluminous natural environment adding broad mix remote beaches secluded coves eco trails breathtaking hikes further add thousands years civilization come previously occupied pre Columbian indigenous peoples onwards La Desirade pearl Caribbean enticing wealth aquatic riches host biodiversity stunning sunset colors make perfect backdrop each cruiser seeking explore diversity across high seas rugged lava coastline far maritime heritage exotic botanical gardens quaint villages find all things true blue ocean endeavors cannot miss these outrageous archipelagos holy grail every type seafarer’s thirst!.

No matter what kind sailor you may be or level expertise have pleasure water there something everyone when comes unique saucy cruising culture within sacred land sumptuous sceneries blessed heavenly hues watch yourself set out exploring fantastic marinas safe harbors thrilling volcanoes deep sunken jungles mystic rainforests habitants living each corner waiting welcome them board now embark crossing boundaries beyond crest horizon look down at hypnotizing turquoise emerald shades azure streams hug thy strand reveal grace secrete Galleon pathways awaits venture ours wildest dreams moved fleet take air giving wings let fullest potential surface discover kaleidoscope wonders paving path ahead ever onward voyage calls again !

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