Best Sailing Destinations In The Caribbean

Best Sailing Destinations In The Caribbean | Life of Sailing

Last Updated by

Daniel Wade

August 30, 2022

The Caribbean is one of the most beautiful and favorable seas to sail, and there are numerous breathtaking islands to visit.

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

In this article, we'll cover ten of the top sailing destinations in the Caribbean region. We'll touch on the destination's history, scenery, and sailing accommodations, along with other attractions unique to the islands.

We sourced the information in this article from travel guides and the testimony of sailors who frequent the Caribbean islands and the Gulf of Mexico.


Table of contents

Sailing in the Caribbean

The Caribbean is a highly popular sailing destination, especially for sailors in the southern and eastern United States. The region is tourist and boat-friendly, and it offers some of the most picturesque islands and coral reefs in the world.

Caribbean sailing promises warm weather and gorgeous water, which is warm enough to swim in year-round. Hurricane season can be a challenge, but the threat is reduced thanks to modern weather technology and careful planning by the sailor.

Here are ten of the best and most beautiful sailing destinations in the Caribbean, along with some of the best attractions to visit.

Top 10 Caribbean Sailing Destinations

We researched the most popular and unique sailing destinations in the Caribbean and found ten countries and island chains that stand out. These locations are accessible to American sailors, and some are U.S. territories that don't require citizens to go through customs.

1. Puerto Rico

Puerto Rico is a U.S. commonwealth located in the northeast of the Caribbean. The island is inhabited by just over three million people, and it's one of the most populous sailing destinations in the region. Puerto Rico is a beautiful island with warm weather and luscious scenery, making it a great destination to sail.

As a populous territory, Puerto Rico has all of the modern infrastructure you'll need. It has full-service marinas, boat repair facilities, and plenty of local spots for food and drink. It's an excellent place to stop for supplies or to spend a week or two. It's one of the most pleasant tropical vacations you can have.

Additionally, Puerto Rico uses the U.S. dollar as its primary currency, so you won't have to deal with currency exchanges and other hassles. U.S. citizens don't need a passport to visit the island, and U.S. flagged sailboats have an easy time finding accommodations. You don't even have to go through customs. However, you will need to bring a U.S.-issued ID card.

2. Belize

Belize is a country in Central America located on the western edge of the Caribbean. The country is known for its tropical forests and sparse population, making it an excellent destination for sailing adventures. Belize is also home to numerous ancient Mayan ruins, which are a major attraction with huge cultural and historical significance.

Belize also has numerous marinas and anchorages, as the country often caters to private boats along its coastline. The coast of Belize offers spectacular views of the ocean floor and marine life, with dozens of natural coves and inlets that serve as ideal anchor-outs.

The natural environment of Belize is stunning, but it's not the only attraction in this tropical region. Belize is home to several well-known resorts and coastal destinations, which offer luxury accommodations, food, drink, and lodging.

3. The Cayman Islands

The Cayman Islands were probably discovered by Christopher Columbus in 1503. The once uninhabited chain of islands, located south of Cuba, offers spectacular sailing and sightseeing. The islands include Little Cayman, Cayman Brac, and Grand Cayman (the largest). Today, the Cayman Islands are a British Commonwealth with about 71,000 inhabitants.

The Cayman Islands are home to spectacular anchorages and an occasionally rocky waterfront, with excellent beaches and marine life. The weather is tropical and warm, and the islands aren't far from the continental United States. Everyone here speaks English, so it's easy to find good accommodations and to socialize.

The Cayman Islands are home to several marinas, charter services, and even a sailing club. The shallow and clear waters surrounding the island make for excellent scuba and snorkeling, and the weather is almost always warm and favorable. Just watch out for hurricanes, which sometimes cross over the island during peak summer months.

4. The U.S. Virgin Islands

The U.S. Virgin Islands is a United States territory officially home to around 100,000 people. Like Puerto Rico, the U.S. Virgin Islands are an easy sailing destination for U.S. citizens. The small chain of tropical Caribbean islands uses the U.S. dollar as its primary currency, and English is the official language.

The islands have a total area of about 133 square miles, making them one of the smaller destinations on our list. The islands are located immediately adjacent to the British Virgin Islands, which are another top sailing destination.

Shallow waters along the coastline make the U.S. Virgin Islands an excellent place to dive, as the region is rife with marine life. There are dozens of smaller islands around the primary islands, which offer opportunities to explore secluded natural destinations.

5. Saint Lucia

Saint Lucia is a Caribbean nation that's known for its beautiful sailing conditions and majestic mountainous islands. The island is also home to luxury resorts and good services, along with protected anchorages for sailboats and yachts.

The official language on the island is French, but most sailing destinations have staff that speak English. The beaches on the islands are some of the best in the world, and the landscape is teeming with tropical plants, brightly colored flowers, and wildlife.

Like most Caribbean sailing destinations, the water around the island has shallow spots that are great for scuba diving and snorkeling. Saint Lucia is an excellent destination for photography due to its unique and iconic rock formations.

6. The British Virgin Islands

The British Virgin Islands are located right next to the U.S. Virgin Islands, and they offer some of the same excellent sailing that the U.S. Virgin Islands offer. This chain of islands is home to about 30,000 people. Sailing is a huge part of life here, and it's the only way to reach many of the most desirable locations.

These small islands are still a commonwealth of the United Kingdom. That means that English is the official language at all British and U.S. Virgin Islands sailing destinations. The official currency is the U.S. dollar, which makes transactions hassle-free for Americans. The islands host an annual regatta which is a great way to make friends from around the world.

The British Virgin Islands have excellent tropical scenery but also numerous coral reefs and rock formations to explore. For example, the Baths of Virgin Gorda are a mystical and popular natural wonder to explore on the islands.

7. Guadeloupe

Located in the Les Saintes archipelago, Guadeloupe is an excellent sailing destination with services and gorgeous spots to anchor out. The island is particularly popular with experienced sailors, and it offers plenty of opportunities to socialize without the crowding of islands that attract more tourists.

Guadeloupe is a French territory with luscious forests and a beautiful coastline to explore. The main island is almost entirely forested, which provides a rare and mostly untouched view of natural tropical life. The largest city, Basse-Terre, is home to the majority of the islands' 395,000 people.

French is the official language on the islands, though many people speak English, and there are facilities for immigration and customs work to be completed. Additionally, since the Island is controlled by France, it's part of the European Union and accepts the euro.

Note that on older charts, the regions of Saint Barthelemy and Saint Martin may be included as part of Guadeloupe, but these regions had a referendum and were detached in 2003. Nonetheless, these nearby destinations make for excellent sailing and exploration.

8. Grenadine Islands

The Grenadines are a world-class sailing destination, with several small islands making up the larger chain. These islands are known for their tropical beauty and seclusion, making them the perfect destination for quiet family trips to the tropics.

Many islands in the Grenadines were once privately-owned but are now uninhabited and rife with stunning scenery.

The rocky Grenadine Islands have numerous reefs and lots of places to anchor out, meaning that the islands can be a fun and affordable place to stay. The island of Carriacou is home to the majority of the population and offers some services to sailboats and other vessels.

9. Grenada St. Vincent

Grenada, a region home to numerous islands, including the Grenadines, is also home to St Vincent. This volcanic island is green and well known for its natural beauty. The capital city Kingstown is home to numerous hang-outs such as bars and restaurants, and it's just one of several seaside towns to explore.

One of the most popular tourist destinations on the island is the Botanic Gardens St. Vincent. The area, which is undergoing constant conservation work, is home to numerous tropical plants and animals, along with colorful and rare island birds.

10. Antigua

Antigua is a flower-shaped island that's known for its rare wildlife and beaches. The island, which has remained mostly isolated for centuries, is home to some of the world's rarest animals, such as the Antiguan Racer snake and the Griswold's Ameiva lizard.

Antigua is an excellent example of the weather and scenery that the Caribbean has to offer. It's a popular destination for sailing and yachting, and there are facilities around the island that cater to sailboats and help owners complete all the travel paperwork.

Antigua is home to a massive regatta that draws hundreds of fast sailboats annually. Antigua Sailing Week is a world-renowned event that's a blast to participate in and watch. During the rest of the year, the island hosts hundreds of boats throughout its many protected coves and inlets.

Best Sailing Destinations In The Caribbean
Daniel Wade

Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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