Caribbean Sailing Vacations is a family 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.

Exploring the Caribbean by boat has been a huge part of our family’s lifestyle since our kids were very young. As a family, we are passionate about delivering amazing customer service and helping guests to experience and love the islands the way we do! So give us a try. We promise to make your yacht charter affordable, make it easy, and make it fun!

Finally, and best of all, your vacation dollars go to support our two Caribbean based foundations. One, Inspiring Children Foundation, is focused on the support of at risk youths and has been incredibly successful. The second one is new, and is focused on providing financial support for the growing homeless pet problem in the Caribbean. With your support, we can make a huge difference in the lives of children and animals in this region of the world.