Caribbean Sailing Vacations is a locally owned and operated company located in the heart of the Caribbean – St. Thomas, the BVI, St. Maarten and Peurto Rico. . Together, we have been cruising, sailing and living in the islands for over 25 years. Our long history here and our involvement in the yacht charter industry and community allow us a unique perspective on the yachts and crews who operate them and on the islands and cultures you will be exploring.

We started and Caribbean Sailing vacations to provide a full service “flip flops on the ground” vacation brokerage in the Caribbean.

We work and play with the crew, so we know them well. We see the yachts frequently, so we know their condition and their features. From the time you land to start your adventure, to the time you say goodbye, you can be assured that we have done everything possible to make sure that the yacht and crew are prepared, that your transition from airport to yacht is smooth and that your every expectation is met and exceeded.

Located in the heart of the Caribbean we offer extraordinary charter experiences catering to those adventurous at heart.

We live, work in and with the charter community on a daily basis. We know the yachts, the crews, and the owners – all partnering with us to deliver affordable, fun charters that create memories to last a lifetime. From the moment you inquire about a charter; from the time you land to start your adventure; to the time you say goodbye….. we are passionate about delivering amazing customer service and helping making sure that your expectations are met and exceeded.

Whether you are a family, a group of friends, or part of a corporate outing – seeking quiet coves, beach bars, historical hikes, raising sails and skimming across the water…or just looking for fun in the sun, you can be assured that Caribbean Sailing Vacations has done everything possible to make sure that everyone has the holiday of a lifetime.

Treat yourself to something special – connect with Caribbean Sailing Vacations