Steven,

It sounds like a fantastic trip. We had thought of doing the same
(flying to Caribbean Islands, Cuba etc.) but possibly with a tour group
like the ones organized by airjourney. You may want visit their
website to get some ideas

http://www.airjourney.com/

What got us into flying was our diving trip at Cayman Brac.
Continental flew us to Grand Cayman. From there, we took a small plane
flying low over the beautiful clear turquoise water with white sandy
bottom dotted with coral reef clusters to Cayman Brac. During the
flight, one of fellow diver told us that he used to fly 'little plane'
but lost his medical due to his diabetic condition. We thought it
would be really cool to get our certificates, own a little plane and
just go islands hopping. After the trip, we started our flying lessons
then later bought a plane. With our instrument ratings, we will
definitely make more long cross country trips (got close to 10,000nm
since last June). Key West, Bimini and Cayman Islands are definitely
on our list of must-do destinations.

Hey, if you have not already done so, you should get into scuba
diving. Cayman Islands have many great diving spots. The feelings you
get while flying or diving are very much similar.

Keep us posted on your planning and the trip itself.

Hai Longworth