Over Cuba
Have fun in the Cayman's I've flown there about 20 times in the last 2 years. As far as an over flight permit; the best place to go is to Universal in Houston or Jeppesen and let their flight planning services take care of it for you. There is also a company in Miami that does it for cheaper, but the on time I did use them they screwed it up and I was denied overflight when only 30NM fomr Cubian airspace, that's a big surprise. About 3 weeks latter I got a bill in the mail from them to boot.
Overflight permits are issued by the country your going to overfly, they are issued for a spific time/date/route ect. (some countries vary) some countries also have a time period in which an overflight will be issued. ie 1 weeks notice/48 hours ect. You could call the Cubian government for the permit (tha's the cheepest way)
One more thing the FAA has put some restrictions on Part 91 IFR flights to foreign countries, I'm not sure how much of the Caribbian (sp?) is alright to fly to. Diffenetly check.
If this is your first trip to MWCR you might want to us a service like Universal to set up "handling" for you. At least on your first trip just so you get to know people. The Cayman's are laid back, Customs is a breeze and the person that comes out to spray" your aircraft's cabin will want paid in cash, our plane was $50US for a Sabreliner.
PM me if you have anymore questions.
PS you will need a passport!!
