Surprised no one mentioned our second favorite, Antigua and Barbuda. Flights a little longer/pricier from US compared to STT but boats usually a little cheaper and no ferry costs/issues so almost a wash price wise. Sunsail is in Nelson's Dockyard and Horizon and Dream Yacht are in Jolly Harbor. Provisioning right across the street in Jolly and the bag boys will take your cart to the boat for you.

With that said it's hard to beat the BVIs for it's short sailing distances, bars and restaurants aplunty and many interesting sights to see on shore!
Windwards - longer distances, boatboys, some incredible voyages and adventures.
SVIs - we love anchoring behind reefs and Culebra has two nice spots on the east side. The Bioluminescent Bay on Vieques is the single coolest thing I've ever experienced.
San Juan islands (PNW) - incredibly beautiful, snow capped peaks in the distance, cold, cold water.
Greece - Study up on med mooring! Really not difficult. Mooring to the quay right in the center of town is so different and fun - usually a taverna or two right across the street! Ionians if you like it slow, Cyclades if you like sailing, sometimes, with gusto (lookup Meltemi winds)! A surprising number of Greeks speak English, especially the younger ones (but I cheated and brought my Greek wife just in case).

Places I'd still like to sail?
Saint Martin
Belize
Bahamas
Australia and some of the Pacific islands