Virgin Island Sailing School was founded in 2010 by Captain Scott Dempster and is the only American Sailing Association (ASA) certified school based in the U.S. We operate from November 1st through July 31st from our base on St. We established our school and charter company here because it is, quite simply, the best place to sail in the world – almost unfailingly warm and breezy, with smooth, calm
waters that are sheltered by surrounding islands. Each day offers new beaches to explore, breathtakingly beautiful anchorages, and seriously notable sunsets. Whether "schooling" or chartering, your itinerary is yours to create. You let us know your idea of a perfect week in paradise, and we’ll do our best to exceed your expectations. No idea where to start? Excellent - we kind of consider ourselves experts at engineering happiness. Our sailing school is the epitome of experiential learning. Classes are integrated into a live-aboard cruise over a 7-night, 6-day period, so you can immediately apply what you’ve learned in each lesson. You will master the ability to be your own captain, whether day-sailing, chartering your own boat with family and friends, or building upon your new knowledge to go anywhere and enjoy the endless adventure of it all. And while there are books, tests and certificates of completion, this is definitely not a traditional classroom environment. You will have plenty of time for recess, your after-school activities are yours to craft, and we promise your school days here in the islands will be like nothing you’ve ever experienced. Philosophically, ASA and all of us at Virgin Islands Sailing School believe that sailing is safe, fun and easy to learn. It’s only complicated and intense if those teaching it choose to present it that way. We don’t. The ocean is waiting. See you soon?
