Englishgal - you clearly need a geography lesson.
Many people confuse Barbados with the Bahamas and consequenly think it's just off the Florida coast - in fact think a thousand miles plus SE of Miami over open water with no effective search and rescue and hundreds of miles between hospitable airports.
So no, not largely in US airspace - other than the part down to Miami - it's starting the trip with the prospect of the over water in a newly purchased thirty year old single with 15 minutes post-PPL - that's the fun part - I did practice over water on the way down to North Perry, my jumping off point, by flying well off the coastline of the Carolinas and Georgia.
The point I was making was that people do extraordinary things with airplanes all the time and without back up teams and massive budgets.
As it happens I need to bring a couple of planes down this coming winter - I did my trip in hurrican season in the summer. So if anyone fancies the idea of making the trip on the basis of a $1/hr dry rental (no commercial needed) do drop me a line and maybe you too can have the trip of a lifetime, rack up twenty hours of real flying - all of course sans TV crew and support crew. There will be two PA38s - fly to Miami, pick up the planes and take your time getting down here - it can be done in two days but taking a week flyinga couple of hours a day is much more fun - once in Barbados stay at my place on the beach then fly back to London - how's that for an adventure
Anyone up for it do drop me a line.
Pace - see my previous post - if you're serious lets me know; would help to have an FAA PPL - US reg planes but they may be on export papers, not too sure yet.
As to insurance - the airplane needs the minimium ICAO cover, which they do. To be safe financially the pilots should have renter insurance - as it happens the standard Avemco renter policy cover takes in the whole of the Caribbean ending about fifteen miles south of Barbados, so only islands not covered are Trinidad and Tobago. In any case we will include whoever wants to make the trip on our list of named insured persons to avoid the potential for subrogation.
Plus if anyone is up for a flying holiday out of Barbados I rent out my US registered IFR PA28-181for US$200/hr wet (no landing fees in Barbados) - the whole of the Eastern Caribbean is at your feet - if you have an FAA licence no hassle to the other islands. Also have some Barbados reg (a Tomahawk and an Arrow) but there is a need to convert to a Barbados licence to fly them between the islands.