It's fun, most islands nickel and dime you to death.... landing fee, tie down fee, departure tax, etc for GA.
Have the FCC permit ....
Miami Center, Radio, San Juan Center, Radio cover most all of the Caribbean...
From what I remember I don't think there is Night VFR most anywhere....
all and all it's great flying... some places you'll need to keep an eye on your aircraft (i.e. Haiti)....