we are organizing exactly these kind of trips in the caribbean. if you are interested please check www.letmekite.com
everybody loves to do that, you visit everyday a new dream spot and have your "hotel" right next to you. another big advantage, you get to know kitespots, which are only accessable by yacht or plane. no crowds... and not to forget the sailing experience. in my opinion a great combination kitesurfing and sailing! it is an unforgetable adventure.
for the price...it depends on: how long, how many people, dates,... just to give an idea: around 100€/day/pers. incl. food and drinks is possible.
feel free to contact me for more questions. i hope i could help a bit. cheers george