Welcome dafrets, looks like you have big plans. You don't mention if your making this trip alone or 2up, but at least you have riding experience. First and foremost, the GL1800 is a big bike, curb weight comes in at some where around 800lbs. On the bright side, once you get her going you feel like your on the sport bike. Seat height on the wing is about 29", things are put together for easy ground reach, you might not be flat footed, but as long as your ready for it you should be OK. The GL is made for a 3600 mile ride, you can't make a better choice for the long run. Your best bet would be to see if you can rent, borrow or demo a wing there on the island before making your final decision for your trip here on the mainland. The only problem I see is that you might like it so much you won't have enough road on the islands to satisfy the need for a long ride!