Windjammer Barefoot Cruises
This great site describes sailing cruises set in the Caribbean. The photographs on this site make it look very tempting.
Offshore Sailing School
Claiming to be the Ivy League of sailing Schools, this school offers courses for beginners as well as experienced sailors in Florida, Chicago and in the Northeast.
This school is based in San Diego but also offers courses in Rhode Island and Maryland. [see mens journal site]