A sailing paradise, paired with rich cultures, cuisines and traditions, the Caribbean is full of adventures and beautiful stretches of coastline where you can sail with your friends and family. Sail the British Virgin Islands and anchor in idyllic bays where you can stop for lunch or a cocktail on the beach. Snorkel with the tropical fish and turtles in the Bahamas and even encounter a swimming pig, or two! (Yes! We’re not joking!) Let yourself go as you sail with the wind in your hair and admire a constant panoramic view of breathtaking nature at its best. 

Sailing boat rentals in the Caribbean are a popular choice of boat and can be found in the following areas of the Caribbean:

British Virgin Islands

Martinique

Bahamas

Saint Martin

Grenada

Saint Vincent and the Grenadines

Guadeloupe

Antigua and Barbuda   

Saint Lucia 

Curaçao

Lacking inspiration or need some tips? Check out our Nautal blog for sailing routes around the BVI, Martinique, Guadeloupe and much more! We calculate nautical miles in our routes and give restaurant recommendations in addition to other random facts and cool things you can do in the area.

Our favourite time of year is spring and early summer, from March to June, when the islands are in bloom and are a pleasure to sail.

The trade winds are perfect at this time of year, though Christmas and Thanksgiving are also popular times of year for sailboat rentals. 

We do not advise sailing in August and September as this is known as hurricane season and various areas are not safe during this time of year. 

The best way to reach the islands is usually by plane, or alternatively you can rent a sailboat in Miami or in the near Florida and sail to Caribbean areas such as The Bahamas. 

Many islands have international airports and you can fly directly or find connection flights.