Well first of all you need to have the proper license, other then for the French Islands and few other you go nowhere with a JAA license.
The easiest place to get your license converted is the DR, it`s really a piece of cake, but then again no chance of renting a plane solo, same in probably most of the other islands.
Your only option is to get an FAA license, there are several companies in Florida (PM me and I will name you a few) that rent planes for solo/PIC flights to the Bahamas, very few, for insurance requirements will allow you to take them to many other Islands, the one I rented wasn`t allowed to go further south then TC.
It will be also very expensive as you will be taking a plane for several days, they will probably charge you extra/day.
I would stick with the Bahamas, Key West and South Florida...way less of a pain in the a** in bureaucracy also.
An other big problem is that you wanna do this flying in the hurricane season.
Last edited by flyingswiss; 26th Mar 2013 at 00:22.