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

We started 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 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 extremely passionate about delivering first class customer service to every one of our valuable clients.

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 rest assured that Caribbean Sailing Vacations will do everything possible to ensure that you and your fellow travellers enjoy a charter holiday of a lifetime whilst making memories that you will never forget.

Treat yourself to something special – connect with Caribbean Sailing Vacations