Thanks for all of the replies. Gives me plenty to think about. The Windwards sound like fun, but now I am thinking they might be a better option once my kids get a little older and can better appreciate the history and culture as well as help with the sailing during the passages. The Abacos are still a possibility and I'll keep looking into them. Belize and the Grenadines, though I am sure very beautiful, seem like they'd be a bit quiet and slow for us. Now I am thinking a ten day charter between all of the Virgin Islands (British, US, Spanish) might be the ticket. That way we can explore some new places and get in plenty of sailing, but still have the familiarity of the Virgin Islands. Now the challenge is finding a company that would let us take a boat between the three island chains. Anyone happen to know if SailCaribe would allow us to charter out of PR
and sail over to the US and British Virgins?
Thanks again for all of the input,