ItalyCharter offers hundreds of options for the Caribbean on a sailing boat: throughout the extensive area that goes from Cuba and the Greater Antilles and through the Lesser Antilles to Grenada. A sailing holiday in the Caribbean is the most fascinating and classic you can aspire to. It is the pure joy of sailing for a sailor in one of the most beautiful areas on the planet. Sailing Caribbean means sun, crystal clear sea, pristine beaches, hidden coves, rainforests. But also nightlife, restaurants, local culture, human warmth. Sailboats can be rented bareboat or with skipper for a surcharge. Choose the island that best suits your needs and select a sailboat from our Caribbean charter operators. You can also contact us as we can advise you on the itinerary so that you can visit more islands in your holiday. Caribbean sailboat to make your cruise an unforgettable experience.