Best Sailing Itineraries in the Caribbean: Must-See Destinations and Hidden Gems

  • Apr 4, 2024
  • Reading time: 4 mins read
  • By Anoushka

Whether you’re looking for a sailing adventure to fulfill or a cruising vacation to remember, these are the best sailing itineraries in the Caribbean. They cover must-see destinations and hidden gems, with plenty of activities and places to explore and relax. 

Sailing through the Caribbean is the stuff dreams are made of, but unfortunately, only a few people get the chance to do it. If you are considering living on island time, you should know that there are more than 7,000 reefs, islands, islets, and cays just waiting to be discovered by you. 

It can be difficult to choose which of these bite-sized locations to visit because they all offer something unique, from the scuba diving paradise of the Canary Islands in the north to the gorgeous desert of Aruba in the south.

British Virgin Islands

The British Virgin Islands (BVI) is an obvious destination for your next sailing vacation with its well-established marina facilities, pristine beaches covered in white sand, and mouthwatering cuisine. Because the winds are expected to be light, and the passage between the islands will be visible to you, this is an excellent bareboat charter choice for sailors of all experience levels.

Sailing Charters BVI can be enjoyed at any time of the year. Want a little bit more excitement? The high season runs from December through April and involves a variety of exciting events, such as the BVI Kite Jam and the BVI Spring Regatta.

During May and June, the islands experience a slower pace and a more tranquil ambiance. The air temperature is slightly higher, the breeze is more bearable, and the rates have been reduced somewhat.

There is an extremely remote possibility of hurricanes occurring during September and October. If you choose the path with minimal danger, you could end up all by yourself at an anchorage with a beautiful beach.


Sailing around Grenada, with its 45 beaches of black and white sand, tropical jungles, beautiful reefs, and natural parks, might easily take up a whole week of your time. Grenada is a great place to visit if you’re looking for an exciting new experience.

Those who have a passion for nature, in particular, will admire the multitude of hiking paths, waterfalls, and coral reefs found on the island, in addition to the native species that include the armadillo, Mona monkeys, calves, dolphins, and manta rays.


The protected harbors, isolated islands, and sailing places that range from easy to hard that can be found across the Bahamas are extremely popular among sailors. And we couldn’t be more in agreement with all the acclaim. 

If you factor in the fact that the winds are moderate and soft, the line-of-sight navigation is straightforward, and there is the opportunity to go scuba diving in some of the most beautiful locations on the planet, you will have discovered a genuine sailors’ paradise.

September through May are ideal for charter a catamaran in the Bahamas since average temperatures range from 18 to 27 degrees Celsius (65 to 82 degrees Fahrenheit). During the summer, the temperature can reach up to 31 degrees Celsius (89 degrees Fahrenheit).

The Bahamas are known for their ability to put on a good festival. While at least one significant event is often held every month, the summer months are especially jam-packed with exciting events like the colorful Junkanoo in July.


All the sailing destinations mentioned above are worth visiting, but you need to decide which of these you want to visit. Want to sail in a hidden paradise? Grenada is the place for you! 

Prefer to bask in the sun and enjoy the beach? Then head on over to the Bahamas! Want both excitement and tranquility? Choose Grenada or the British Virgin Islands! No matter which sailing itineraries you choose, your trip will be nothing short of perfect.


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