I've sailed a lot in the Eastern Caribbean. Between the Virgin Islands and Grenada there are a dozen major islands and lots of smaller ones, including Anegada, Virgin Gorda, St. Martin, St. Barts, Anguilla, Antigua, Guadalupe, Martinique, St. Lucia, St. Vincent, the Grenadines, etc, etc, etc. Passages between islands are only a few hours, so you don't have to sail at night and the trade winds are usually blowing great from December to May.
Now that I'm a kiter I want to combine sailing and kiting by doing a 1-2 month cruise in these waters with a focus on seeking out great spots for kiting. We'd visit the standard kiting spots on the major islands and in addition find little-visited spots that can only be reached by boat. Of course in addition to kiting we could snorkle, dive, visit bars/restaurants, sightsee, and simply hang out on some beautiful Caribbean islands.
We'd charter a 40-something foot cruising Catamaran with 3 or 4 cabins and share all costs. People could fly in and join the cruise for only a week or 2 if they can't make the whole trip.
Has anyone done such a trip in the Eastern Caribbean? Any advice on where to go?
Also, if you'd be interested in joining such a cruise, let me know. I'm targeting March-April 2013.