A trip to the Caribbean is merely about the adventures of the sea where warm winds, crystal clear waters and midnight waves of the ocean calls to all of us. No matter what type of adventure you like, whether lounge on the sundeck of a yacht or ride a vessel of your own, the Caribbean has its all to make the perfect sailing destination which allow you to sail entirely on your own terms. With different levels of experience on deck, some visitors prefer to have a professional crew to help navigate while others like to handle things on their own. They make things simple by hopping on a charter with a pre-determined itinerary and simply ride along, being in charge of their own craft and create the perfect journey step by step. Just a few hours of sailing is more than enough before coming back for a good night’s sleep in a private beautiful villa on land. Or even better if having the time to spend the night on the boat and take a round-trip the islands for a few days. 

In this posy, you’ll find some of sailing spots and on-shore stops along the coasts of Caribbean islands for a day-trip, or even multi-day adventure.

Before you get on the water…

Be sure to avoid stormy weather and temperamental waters by sailing between January and March when the weather is ideal.

You have three different options for renting a yacht, vessel or sailboat in the Caribbean by booking directly with a charter company or a charter broker who is a travelling agency, helping find the right type of boat for you. If you’ve decided to travel with a professional crew, a broker will help you book a good team. There are numerous great small businesses across the Caribbean islands with fully catered day-cruises and wonderful itineraries.