I did the island hopping thing years ago, flew for a charter company outta St Croix. The main problem with it was that I was always on call, and its pretty hard to enjoy the sand or the rum when you're wearing a beeper. I also tried the island commuters while I was there, but they have the same problems as commuters everywhere and anyway prefer to hire local pilots. My favorite flying job was in Alaska, worked up there for a year. I've often thought about going back but I was 20 years younger then and the winters get so damn cold LoL. I think what I'd like to do now is find a decent paying ground hog job that I don't hate to pay the bills, and tow gliders on my days off. Sounds simple enough yes?
I think you should just bite the bullet, take some time off and go get a pilots license
Which rating you get is up to you, but we get a LOT of people at my school who stay with us for days at a time and bang out their glider ticket in a matter of days. Here's where I tow:
http://www.bermudahighsoaring.com/
And of coarse Facebook:
http://www.facebook.com/home.php?ref...88101617879369