dtj,
As LH44 Anne said, your question is so open-ended that it's hard to answer. Why do you ask--are you planning to
charter, or will you be sailing your own
boat there? Will you be spending a week or the whole cruising season? The Caribbean is huge--is there a specific area you're interested in? A bit more substance to your question would give people a lead as to how to best answer in a way that addresses your interests.
That said, I'll focus on the Lesser Antilles. My wife and I greatly enjoyed
Dominica. It's a natural paradise with plenty to do and see if you like hiking and Nature. We loved
Nevis for it's friendly people, it's beauty and it's laid-back atmosphere (that's why we moved her six years ago). The Grenadines are fun to visit--snorkeling and hike the
Tobago Cays, visiting the many small islands there. Bequia is kind of funky/artsy and fun to visit. For first-time charterers, you can't beat the
Virgin Islands.
Martinique is very French and offers a lot to see and do. St Barth has great restaurants and
shopping.
St Martin is a bustling tourism center with many shops and restaurants. Antiqua has some interesting historical sites and wonderful
remote anchorages amongst little islands and
coral reefs.
Actually, the best
advice is to see them all. We spend two years cruising up and down the chain and enjoyed each of the island for their unique character.
Here are a few links to threads on the topic that have a lot of suggestions...
http://www.cruisersforum.com/forums/...bbean-587.html
http://www.cruisersforum.com/forums/...ean-52206.html
http://www.cruisersforum.com/forums/...ean-20571.html
http://www.cruisersforum.com/forums/...ter-77397.html