We are also taking our first ever Caribbean vacation (this summer), and I had almost the exact same wish-list that you have.

I chose Tortola - BVIs. If your research suggests this as a possible destination, I recommend Traveltalkonline as an excellent source of information.

Isn't planning a vacation fun?!!! Good luck with your research.....

Our family just stayed at the Jolly Beach resort in Antigua. Antigua has mountains and lush greenery. Nelson's Dockyards and Shirley Heights are impressive historical sites, converted into shops and restaurants. The Jolly had a wide and very,very long sandy beach. There are about 8 Hobie Cats available for sailing. The rooms were large and clean. Our only complaint was that there was not a bar on the beach, (They were all set back a distance.) At the southern end of this beach was a small resort called Coco's which consisted of cabins built into the cliff with outdoor showers etc. It looked very cool. Around the corner was Cocobay, also in the cliffs, which is bigger and gets good reviews. Antigua is fairly easy to get to. We recommend taking the Wadadli Catamaran around the Island. it stops for snorkling, and serves lunch. You see the dramatic Atlantic side of the Island (and Eric Clapton's establishments). At the Jolly Resort, the local music was excellent with no rap/hiphop. We enjoyed our stay.