Subject: BVI, Tortola and the Caribbean
I've visited many of the islands, coming from the sea (I was a yachtie, sailing the island chain for 2 years) rather than from land. Cane Garden Bay is very lovely, but quite isolated. Not sure whether you find a hotel with swimming pool. Things may have changed, since I was last there, 8 years ago. A possibility is Virgin Gorda (also part of the BVI), where you find Biras Creek Resort, for example, an upscale hotel with very friendly staff. Close to it is the Bitter End, where you can enjoy lively evening activities. (As a hotel, I would prefer Biras.) The Gorda sound has plenty of things to do, good beaches, watersports of every kind, walking, hiking, etc.

Personally, I searched for the authentic Caribbean experience, beyond the mega hotels and rum-punch bars in every bay. That wasn't easy. My favorites were Grenada (spice island in every sense) and Dominica (not to be confused with the Dominican Republic). Dominica is said to become the next St. Barts, but fortunately not yet. It's as yet underdeveloped with budget hotels and guest houses, fantastic rainforest and a few beaches. Nightlife? Practically zero.

A compromise between Key West and Cane Garden Bay might be St. Maarten/St. Martin. The Dutch side is overdeveloped, but offers good night life. The French side much less so, much more upscale and with wonderful restaurants in Marigot and Grand Case. It's very easy to go from one side to the other, mini-buses make frequent trips for a reasonable price ($1?), no borders. Also, from St. Maarten you can take excursions to Anguilla or St. Barts. As a choice, I would take a hotel on the French side, where life is more relaxed, less American.

Hope this helps, Frieda