I started with a sailing course in St Thomas and it was the most fun vacation I've ever been on. It was a combined ASA 101 and 103 class over 8 days of living aboard and sailing around the virgin islands (both US and British, including Tortola). We visited a different island every day, sometimes 2 per day. We'd sail starting early in the morning, arrive somewhere around noon, eat lunch either aboard or ashore, have the "classroom" part of the class (usually ashore in a bar), then swim or whatever, have dinner, explore the island, etc. Some days the "lunch" stop would be early enough that we'd continue sailing to a different anchorage for the night. The school was the Maryland School of Sailing and Seamanship, which runs their summer classes on the Chesapeake and their winter classes out of St Thomas. I highly recommend them. I have no affiliation other than being a satisfied customer.