QUOTE(kilgiraffe @ Nov 5 2009, 02:33 PM)

You may also have fun crewing on private boats if you so desire.
Backpacking, the only islands that would be really worthwhile would be the bigger ones - Cuba, Jamaica, Puerto Rico and possibly the Dominican Republic. The smaller ones are more geared for tourists unfortunately

Sleeping outside.. I don't THINK you should have many problems, just be smart!
Basically - the Caribbean isn't really known to be an easy backpacking location. Maybe thats part of the fun of it though, finding a way to do it!

That's a good idea, haven't thought about that yet..
Thanks!
How about getting other jobs?
Well I would like to be alone from time to time on some island so I'm okay with being on smaller islands, maybe some of them don't have that much tourists?!
Be smart? Meaning, be careful cause it is not allowed?
Yeah that's why I was thinking about having the Caribbean on my list...
QUOTE(jeremystravels @ Nov 5 2009, 03:47 PM)

Getting the logistics of airfare from one island to another is quite a headache too. Most airfare goes from a major hub - like Florida, rather island to island. To be honest I have found taking a cruise much cheaper than island hopping - although you get less than half a day in each place. Then you would know where you'd wanna go back to once its over.
I know I already checked the airfare, but that's too expensive, especially if you try to go backpacking and just make money in some places...
Cruise? Humm I bet that is too expensive as well, and it's really not what I was looking for to do in the Caribbean..
I just wanted to take some time off and enjoy life..