How long will you be there? What kind of experience do you have?
Staying around St. Martin can be ok for a
novice sailor, but the passages to the nearby islands will be awful tempting. St. Barths is a beautiful 4 hour reach and of course an amazing
destination. The
diving is spectacular as well (worlds better than St. Martin), I suggest Plongee Caraibes as an operator.
Depending on the charter company,
Saba is a nice sail and easily my favorite island in the
caribbean. It also depends on the time of year your going as there are moorings on the leeward side of the island which would be open to northerly swells in the
winter. The diving is incredible.
If I was staying on St. Martin....
Grand Case, Tintamarre, and Marigot are my top picks. A quick sail over to Road bay on
Anguilla is nice for some variety.