We have been going back and forth with going on that sailing. I think we may go on May 15 insteady since being a weekend to a weekend it is easier to balance days off at work and stuff. I enjoy sailing out of NY, only disadvantage is the seas can get a little rough down the atlantic and it isn't as warm as sailing out of FL.
San Juan...depends on the time you are there. There was a segway tour that was there that was pretty cool, not sure if they still do it or not, haven't been there in a while.
St. Thomas...BEACH. This is one of my favorite islands for the beach and there are tons to choose from depending on whether you want quiet and secluded or hot and happening.
Grand Turk...take a shore excursion...DUNE BUGGIES are a BLAST!
Have fun and will let you know if we decide on this date or not.