I'm in Miami, fly a lot to The Bahamas and have been to the Caymans (but haven't flown in). While I don't have firsthand experience, I know that it's a pretty straightforward trip. You need to be on an International flight plan, get Cuban approval for overflight at least 2 days in advance (which is routinely granted) and be cleared by the Cubans into their airspace. I have also heard (but not verified) that it's an IFR flight over Cuba, which may affect VFR-only pilots.
A good webpage on Cayman trips is at
http://www.planeandpilotmag.com/cont...es/havana.html and has useful phone numbers. The return trip, especially crossing the ADIZ into the U.S., needs special attention. If you've never flown into the Caribbean and back, you might find two pages at
www.SkymasterUS.com helpful. "Ditching Checklist" provides pre-flight preparations for over-water flights as well as ditching procedures. "Flight Procedures for The Bahamas" covers many of the procedures which will apply to a Cayman trip.
Incidentally, although I haven't announced it yet, I'm in the early stages of preparing a two-day, one-night escorted trip to The Bahamas for those attending the SOAPA meeting in Key West in May who can spare an extra two days (look in the Home page for the meeting announcement). It will give us a chance to apply these preparations and procedures, as well as fly over gorgeous turqoise waters, stay at beachfront villas for about $75, and enjoy some of the most beautiful beaches in the world.
Ernie