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The Best Caribbean Sailing Locations

Have you noticed the significant uptick of people who post Instagram photos and Facebook photos on a boat on a Caribbean island? There are a few reasons that sailing holidays have become some of the most sought after and enjoyed holidays in the last few years.

  • Celebrities have been filming music videos on boats for years
  • Influencers started renting boats between groups for some unique holiday opportunities
  • The price of a boat rental with a captain has reduced significantly in previous years
  • You can enjoy a stunning holiday and remain out of the throngs of tourists

So why should the Caribbean be top of your list for a sailing holiday?

Sailing in the Caribbean

The Caribbean has been one of the most popular destinations for people all over the globe. It offers exquisite food, stunning views, warm sands, and some of the most friendly people in the world – and of course, the water is beyond beautiful.

It can be likened to a holiday in paradise.

What is potentially the most exciting thing about heading to the Caribbean for a break – the water is warm enough to enjoy almost all year round.

Here are just a couple of places that you can enjoy:


If you are into wildlife that can’t be found anywhere else and islands that are unique in terms of shape, then Antigua is the place for you. What makes Antigua so special is that for a long time, it was isolated, and since not many people visited there, the wildlife was able to flourish.

It offers some of the most beautiful scenery, and the weather is more than a little welcoming; it is one of the most popular places for sailing because it is so temperate – consider a catamaran charter from Antigua a complete must. 

If you really want to make the most of the sailing, then check out Antigua Sailing Week and watch some of the biggest and best boats around.

Grenadine Islands

Considered a world-class sailing destination, if you like to soak up the sun and catch some gentle waves, then this small island is perfect. Grenadines Islands are perfect for people who want to experience a little seclusion surrounded by breathtaking tropical scenery.

Some of the islands of the Grenadines use to be owned privately, but now they are open to the public, so there is even more to explore.

The Grenadine Islands offer the opportunity to swing amongst plenty of reefs and what can be even more enticing for people is that it is reasonably priced too. Making it one of the best places for people who want to experience heaven on a budget.

The British Virgin Islands

The BVIs are so popular because they really do offer something for everyone. The same incredible sailing that can be enjoyed in the U.S. Virgin Islands can be done here. The BVI population is relatively low at just 30,000, but sailing is part and parcel of everyday life.

These little islands are still a part of the British Commonwealth – so you don’t need to worry about quickly learning the local language; everyone speaks English. The U.S. dollar is the national currency, which makes transactions simple for Americans.

BVIs offer plenty of natural wonders to explore, too – making them top of the list for people who love sailing and sunshine.

Puerto Rico

A warm weathered island with some of the richest and most luscious scenery around Puerto Rico.

If you’re traveling from the U.S., you’ll be happy to know that the currency for Puerto Rico is the U.S. dollar, and what’s more, as a U.S. citizen, you won’t even need a passport. So long as you have your U.S.-issued I.D. card, you are free to travel there.

Puerto Rico has over 270 miles of coastline and 300 beaches and is famous for its clear crystal waters, stunning white sand beaches, and weather that is welcoming all year round.

And for those who want to experience paradise with their family, there are more than a few family-friendly beaches like Luquillo Beach.

The Cayman Islands

Little Cayman, Cayman Brac, and Grand Cayman are some of the largest islands – but there is plenty to explore. Just south of Cuba, the weather and the water is welcoming and temperate.

The Cayman Islands are known for some of the best anchorages, sailing clubs, marinas, and excellent beaches.

Sailing is part and parcel of everything that makes up life on the Cayman Islands, and as a British Commonwealth (just like the BVI), everyone speaks English – so it is easy enough for tourists to get around the island and find great places to eat and drink.

For those who like water sports, the Cayman Islands are perfect for it.

Saint Lucia

Saint Lucia is one of the best places for those who enjoy taking photos when they’re on vacation. It’s not just the amazing sailing conditions, though; it is surrounded by majestic mountains. Saint Lucia has plenty of incredible services, delicious places to eat, and many luxury resorts.

Making it easy to switch between spending a few hours on your sailboat and enjoying the delectable cuisine of the island.

For those who enjoy water sports, there are plenty of shallow places to swim, snorkel, and scuba dive.

With such hospitable waters, the real question is how many of the islands you will choose to visit.