Your Caribbean vacation is not complete without a Private Sail Trip with Octopus. Here is your opportunity to live the dream for a day! Octopus Sailboat Charters provides the best variety, service, and value for any sailing experience you desire. This is your boat for the day, so you can set the itinerary. Whether you’d like a romantic sunset sail, a sailing tour around the island, a few hours, or just a day on the water, it’s totally up to you! We are open every day of the week and will be sailing any time you wish from early in the morning until late at night.