Sailing In The Caribbean

In 2015, my husband and I bought a sailing vessel in the Virgin Islands, quit our job in New York, and spent a year sailing from the Bahamas to the Caribbean and spending time on the islands of Venezuela and Florida. For us, spending in the Caribbean with the large and friendly communities of cruise ships and islands became part of our lives.

That’s not our story, but it’s a story that happens almost every day. And it’s really a nice story. Not only because of its stereotype but more of its potential. It describes the beauty of the Caribbean islands in just two sentences.

The Caribbean Sailing Paradise

Beautiful places in the Caribbean are Antigua and Barbados and St. Martin, a French-speaking island. More than 5,000 islands, reefs, and bays make the Caribbean a picture-book paradise for sailors of all experience levels. If you want to sail a lot, you should know that there are strong currents and high waves on most islands’ north and east sides, especially in the Atlantic as opposed to the Caribbean. The Caribbean offers a variety of sailing opportunities for different skill levels. The islands are easy to reach and only two hours away from the island.

The Most Exciting Islands Of The Caribbean

Popular places to visit by boat are Antigua and St. Barts, Anguilla, St. Martin, the British Virgin Islands, the U.S. Virgin Islands, and the Grenadines. Many can be seen from above. More and more crews of luxury yachts are starting to explore some of the more exotic and remote Caribbean islands – so ask your charter broker or captain for more information about these islands. Whether you want to get away from your luxury yacht charter and escape the Caribbean coast, these islands offer a world of fun to dive into.

Canouan Petit St. Vincent

Suppose you want to combine sailing with a luxury shore holiday. In that case, Canouan Petit St. Vincent is home to two of the most exclusive resorts in the Caribbean island of Mandarin Oriental Petit St. Mustique, a private island chain of exclusive villas and one of the time-honored luxury hotels, The Cotton House. The islands are a string of pearls on the Caribbean coast of every country nestled between Mexico’s Yucatan Peninsula, a hair taller than New Jersey and Belize, and with all the elements that sailors love – turquoise waters, steady breezes, palm-shaded beaches, healthy barrier reef, and the freedom to wander at will. It is located in the heart of the eastern Caribbean chain and boasts beautiful palm-riddled beaches, pristine rainforests, and of course, the iconic Piton Mountains.

Sailing Jamaica

Jamaica is one of the most colorful islands you have ever seen, even by Caribbean standards. With its ubiquitous island culture, you can experience Caribbean food, lively music, and beaches that invite you to nap for hours. Jamaica is quieter than the rest of the Caribbean and perfect for a sailing holiday for people who want to replicate the peace of their boat ashore.

Tahiti , Bora Bora and Moorea

Tahiti and the surrounding islands have a number of fantastic places to sail, including Huahine, Bora Bora, and Moorea, but these are the best. There is no other destination in the world that offers such a choice of crystal clear waters, islands, and sailing conditions. Last but not least, we have the British Virgin Islands on our list of the best Caribbean boat destinations.

The British Virgin Islands

Sailing in the British Virgin Islands is the Caribbean paradise you can imagine. The islands, which cruise in the calm waters of the Caribbean, provide easy visibility and trade winds to keep your course stable. The island’s tip is rounded off by a stop at the world-famous Errol Flynn Marina in Port Antonio, known as one of the best sailing areas on the islands, where enthusiasts cruise from around the world.

Despite being the cream of the Caribbean, the Virgin Islands are the creme de la creme of yachts, and in high season, they are littered with boats so that you can anchor at your desired lunch spot. The season in which you sail through the Caribbean is very important when planning your trip. Boating is essential on St. Croix to the local economy, but less so on St. Thomas and the British Virgin Islands, so if you want to sail the Virgin Islands, plan accordingly.

Pig Beach

If you want to integrate some activities into your Caribbean sailing vacation, you can go to Pig Beach to swim with the pigs, walk on the pink beaches, or snorkel in the Reefs.

The Weather Window

To avoid stormy weather and temperamental waters, plan your Caribbean sailing holiday between January and March. If we have not yet done so and you are convinced, you can be sure that you can sail in the Caribbean on your own terms. You can choose to charter your private yacht with a captain, set sail for your dream Caribbean destination, or hire an experienced skipper for your entire trip for just one or two days.

Hurricane Season

You will have a safer and more enjoyable sailing experience in the Caribbean if you arrange your trip around the general forecast, so stay tuned. September is the primary month for severe weather in this area, so sailors should be careful when sailing in this area. September can be the month when the Caribbean experiences the worst weather, so sailors should be extra cautious when sailing in this region.

Best Time For Sailing In The Caribbean

On average, June is one of the safest months in the Caribbean, as hurricanes are rare and thunderstorms are occasional. It is easy to see why the Caribbean is a dream sailing destination for many people. The best time to sail the Caribbean towards the beginning and end of summer is when the weather is warm and the conditions stable.

For many people around the world, the Caribbean Sea is their gateway to sailing and vacation. The year-round sunny weather makes it a constant in people’s holiday plans and a perfect choice for winter sailing. It happens that summer is the best time to sail in the Caribbean Sea, but it is important to watch for thunderstorms.

The Living Basics

There are a million questions to wade through, so we thought we would offer five questions we receive about sailing in the Caribbean and link you to this page to answer them. We have outlined a few of the most popular islands and some of the best the Caribbean has to offer for your sailing holiday. Food, medicine, and other essentials are not always available in the smaller island states of the Caribbean, which sailor tourists often visit.

The Bottom Line

The Caribbean is one of the most popular charter destinations worldwide, with crystal clear waters, white sandy beaches, and over 5,000 islands and bays to explore. The Caribbean is a top yacht destination for racers, families, and cruisers alike, with a perfect blend of culture, pristine beaches, and ideal sailing conditions. The places are beautiful, warm, fantastic beaches, and interesting cultures. They have a huge selection of crewed yachts, luxury yachts, and superyachts that you can rent to enjoy a wonderful holiday in the various island groups.

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