VFR around the Caribean - charter / licenses / recommendations?

[Faehnrich]

hi folks,

i am an german pilot, european ppl easa license for vfr day + night, english language proficiency level 4. south african validation.
400 hrs flighttime in diffrent countries in europe and south africa.
my spanish is intermediate level.

i am thinking about making a trip round the caribean, something like that (http://skyvector.com/?ll=18.800238088088427,-86.47998046294481&chart=301&zoom=13&plan=A.K7.KMIA:A.MY.MYNN:A.MB.MBGT:A.MD.MDPC:A.TA.TAPA:A.TV. TVSV:A.SV.SVMG:A.TN.TNCC:A.SK.SKBQ:A.MP.MPTO:A.MN.MNPC:A.MM. MMOX:A.MM.MMPB:A.MM.MMVR:A.MM.MMUN:G.21.860988911081265,-84.93200683003462:A.K7.KMIA) (rough plan).

would be happy to get recommendation concerning where to charter an airplane and additionally
what type of licenses are required to do this trip.
could i charter and fly with my easa ppl somewhere?
or is n-reg acft + us ppl the best choice?

which are the musts / "places to be" on this trip ?

thank you for any hints !

Pavel

[flyingswiss]

It will be very hard to find an airplane or anyone willing to rent it to you for that sort of trip, main reason being insurance. And with your flight experience I would definitely not do it alone.

To fly any airplane that is not reg in a EASA country you will need a validation, only the French Islands and French Guiana have F- reg airplanes (EASA).

Since you plan on depart/rent from the USA you will need a FAA license.

Many flight school in Florida rent airplanes to be taken to the Bahamas and TC, some allow you to take it to Mexico also.

Check Baja Bush Pilots, Caribbean Flying Adventure and Pilotpub.

If you do end up doing this trip, I would advise to stay clear of Venezuela.

[-Doc-]

So what you ended up with? I wanna go for a trip myself