+44 7393 450837
Follow on

What Are The Caribbean’s Top Ten Most Popular Sailing Destinations 2022

What Are The Caribbean’s Top Ten Most Popular Sailing Destinations.

If you want to invest as an expat or high-net-worth individual, which is what i specialize in, you can email me (advice@adamfayed.com) or use WhatsApp (+44-7393-450-837).


The Caribbean is one of the most beautiful and welcoming waters to cruise, with a plethora of magnificent islands to explore.

Puerto Rico, Belize, the Cayman Islands, the US Virgin Islands, Saint Lucia, the British Virgin Islands, Guadeloupe, the Grenadine Islands, Grenada, St. Vincent, and Antigua are the top sailing destinations in the Caribbean Sea.

We’ll go through ten of the best sailing spots in the Caribbean in this article. We’ll discuss the destination’s history, beauty, and sailing accommodations, as well as other island-specific attractions.

The information in this article was gathered from travel guides and personal accounts of sailors who frequent the Caribbean islands and the Gulf of Mexico.

While Sailing In The Caribbean

Sailing in the Caribbean is very popular, especially among sailors from the southern and eastern United States. The region is tourist- and boat-friendly, with some of the world’s most beautiful islands and coral reefs.

Sailing in the Caribbean guarantees nice weather and beautiful water that is warm enough to swim in all year. Hurricane season can be challenging, but owing to sophisticated weather technology and cautious planning by sailors, the risk is lessened.

We looked into the most popular and interesting sailing spots in the Caribbean and discovered ten standout countries and island chains. These places are accessible to American sailors, and some are US territories where residents are not required to go through customs.

Here are ten of the Caribbean’s best and most picturesque sailing destinations, as well as some of the best sights to see.

pexels asad photo maldives 1450353
What Are The Caribbean's Top Ten Most Popular Sailing Destinations 2022 3

Puerto Rico

Puerto Rico is a United States commonwealth in the Caribbean’s northeast. The island is one of the most populous sailing destinations in the region, with a population of slightly over three million people. Puerto Rico is a lovely island with pleasant weather and lush scenery, making it an ideal sailing destination.

Puerto Rico, as a populated territory, offers all of the modern infrastructure you’ll require. It has full-service marinas, boat repair shops, and a variety of local restaurants and bars. It’s a great area to get supplies or stay for a week or two. It’s one of the most relaxing tropical getaways available.

Furthermore, because Puerto Rico’s major currency is the US dollar, you won’t have to worry with currency conversions or other inconveniences. Citizens of the United States do not require a passport to visit the island, and sailboats flying the American flag have an easy time securing accommodations. You are not need to go through customs. You must, however, bring a valid United States identification card.


Belize is a Central American country on the western coast of the Caribbean Sea. The country is recognised for its tropical forests and limited population, making it an ideal sailing destination. Belize also has numerous ancient Mayan ruins, which are a popular tourist destination with significant cultural and historical significance.

Belize also offers a plethora of marinas and anchorages, as the country’s shoreline is frequently used by private boats. With scores of natural coves and inlets that serve as ideal anchor-outs, Belize’s shoreline offers breathtaking views of the ocean floor and marine life.

Belize’s natural environment is beautiful, but it’s not the only reason to visit this tropical country. Belize has a number of well-known resorts and coastal destinations that provide luxury accommodations, food, and lodging.

Cayman Islands

Christopher Columbus is thought to have discovered the Cayman Islands in 1503. The once-uninhabited cluster of islands south of Cuba offers fantastic sailing and sightseeing opportunities. Little Cayman, Cayman Brac, and Grand Cayman are among the islands (the largest). The Cayman Islands are now a British Commonwealth territory with a population of around 71,000 people.

The Cayman Islands have beautiful anchorages and a rocky coastline, as well as fantastic beaches and marine life. The climate is tropical and pleasant, and the islands are not far from mainland America. Because everyone knows English, finding nice lodging and socialising is simple.

There are various marinas, charter businesses, and even a sailing club on the Cayman Islands. Scuba and snorkelling are great in the shallow, clear waters surrounding the island, and the weather is nearly always warm and pleasant. Just keep an eye out for hurricanes, which can hit the island during the summer months.

The U.S. Virgin Islands

The US Virgin Islands are a US territory with a population of roughly 100,000 people. The US Virgin Islands, like Puerto Rico, are a popular sailing vacation for Americans. The US dollar is the primary currency on this small chain of tropical Caribbean islands, and English is the official language.

The islands cover roughly 133 square miles in total, making them one of the more compact sites on our list. The British Virgin Islands, another popular sailing destination, lie just near to the islands.

The US Virgin Islands are an ideal area to dive because of the shallow waters along the coast and the abundance of marine life. Around the main islands, there are dozens of smaller islands that provide possibilities to visit hidden natural areas.

Saint Lucia

Saint Lucia is a Caribbean country recognised for its spectacular hilly islands and wonderful sailing conditions. There are also luxurious resorts and excellent services on the island, as well as safe anchorages for sailboats and yachts.

Although French is the official language on the island, most sailing spots offer English-speaking employees. The islands’ beaches are among the best in the world, and the scenery is lush with tropical flora, vibrant flowers, and fauna.

The ocean around the island, like most Caribbean sailing locations, contains shallow places that are ideal for scuba diving and snorkelling. Because of its unique and renowned rock formations, Saint Lucia is an outstanding photography destination.

British Virgin Islands

The British Virgin Islands are immediately near to the United States Virgin Islands, and they provide some of the same great sailing opportunities. Approximately 30,000 people live on these group of islands. Sailing is a big part of life here, and it’s the only way to get to a lot of the best spots.

These little islands are still part of the United Kingdom’s commonwealth. That implies English is the official language of all sailing destinations in the British and US Virgin Islands. The US dollar is the national currency, making transactions simple for Americans. An annual regatta is held on the islands, which is a terrific chance to meet people from all around the world.

The British Virgin Islands provide beautiful tropical landscapes as well as a variety of coral reefs and rock formations to explore. The Baths of Virgin Gorda, for example, are a mystical and popular natural wonder to visit on the islands.


Guadeloupe, located in the Les Saintes archipelago, is a wonderful sailing location with facilities and beautiful anchoring spots. The island is very popular with experienced sailors, and it provides plenty of possibilities to mingle without the crowding that occurs on islands that attract more tourists.

Guadeloupe is a French overseas territory with lush forests and a stunning coastline to explore. The main island is nearly totally forested, providing a rare and mostly unspoilt glimpse of tropical life. The majority of the islands’ 395,000 population live in Basse-Terre, the largest city.

Although many people understand English, French is the official language of the islands, and immigration and customs procedures can be done there. Furthermore, because the island is under French authority, it is a member of the European Union and accepts the euro.

On older maps, the regions of Saint Barthelemy and Saint Martin may appear to be part of Guadeloupe, however in 2003, both regions had a referendum and became independent. These nearby sites, though, are ideal for sailing and exploring.

Grenadine Islands

The Grenadines are a world-class sailing destination, consisting of a wide series of small islands. These islands are noted for their tropical beauty and solitude, making them ideal for tranquil tropical family vacations.

Many of the Grenadines’ islands were originally privately owned but are now unoccupied and surrounded by breathtaking beauty.

The rugged Grenadine Islands contain various reefs and plenty of anchoring spots, making them a pleasant and economical place to visit. The majority of the population lives on Carriacou Island, which also provides certain services to sailboats and other vessels.

Grenada St. Vincent

St Vincent is located in Grenada, which is home to a number of islands, notably the Grenadines. This green volcanic island is noted for its natural beauty. Kingstown, the main city, has a variety of bars and restaurants, and it’s only one of several beach towns to visit.

The Botanic Gardens of St. Vincent is one of the island’s most prominent tourist attractions. Numerous tropical plants and animals, as well as beautiful and unique island birds, may be seen in the area, which is constantly being conserved.


Antigua is a flower-shaped island with uncommon animals and beautiful beaches. The Antiguan Racer snake and the Griswold’s Ameiva lizard are among the world’s rarest creatures, and the island has remained mostly isolated for generations.

Antigua is a great example of everything the Caribbean has to offer in terms of weather and landscape. It’s a popular sailing and yachting destination, and there are facilities on the island that specialise to sailboats and assist owners with all of the necessary paperwork.

Antigua hosts an annual regatta that attracts hundreds of fast sailboats. Antigua Sailing Week is a world-famous event that is both entertaining to participate in and observe. Throughout the rest of the year, hundreds more boats visit the island’s many protected bays and inlets.

Pained by financial indecision? Want to invest with Adam?

smile beige jacket 4 1024x604 2

Adam is an internationally recognised author on financial matters, with over 760.2 million answer views on Quora.com, a widely sold book on Amazon, and a contributor on Forbes.

Leave a Reply

Your email address will not be published. Required fields are marked *

This website is not designed for American resident readers, or for people from any country where buying investments or distributing such information is illegal. This website is not a solicitation to invest, nor tax, legal, financial or investment advice. We only deal with investors who are expats or high-net-worth/self-certified  individuals, on a non-solicitation basis. Not for the retail market.



Gain free access to Adam’s two expat books.

Gain free access to Adam’s two expat books.

Get more strategies every week on how to be more productive with your finances.