Moving to an island...maybe...please help

So, I'm pretty effing frustrated after doing my taxes today. I've never owed money before, but I owe more than $1,000 to the federal government in a time when I was expecting a nice refund to balance things out. I've pretty much had it.

I'm considering -- very seriously, have been for a while, but now I'm close to pulling the trigger -- selling all my possessions and moving to a tropical island to erase myself from the ever-growing radar. If I'm not gonna have money, I might as well live on a beach with crystal clear water. With any luck, I'd catch on with some snorkeling tourism-type place for food money.

I've been to the U.S. Virgin Islands, but know nothing else of other tropical islands. I know many of you are well-traveled, so are there any places you'd recommend?

 

Man, if you're ready to move to an island paying $1K, I'd hate to see what you'd do if you were me.

Move to Mars, maybe?

 

Welcome, my friend.

 

That's not the entire reason...I've always wanted to do that. This is just the tipping point that might make me follow through with my plan.

 

Fuck an island. Move somewhere in Mexico or Central America. Build boats or teach Americans how to snorkel, like you suggested. You know, like Andy Dufresne.

 

TBF, I've always wanted to live on an island, though. I guess the real question involves moving. Do I have to jump through a bunch of hoops, or can I just buy a plane ticket or boat ticket and stay?

EDIT: I also want to make it very clear I'm not looking for sympathy, nor am I overly depressed, nor am I looking for attention. I'm legitimately serious about this, and I know many members of the board might have knowledge of how to proceed. I thought this place would be as good as any to start researching. Wikipedia is next.

 

Dude, I'm thisclose to moving to Canada.

 

My wife and I took a cruise on our honeymoon. We went diving at every port where the shipped docked. In Grand Cayman our dive master was a former UAW guy from Detroit who had been making excellent coin in the union. However, his expenses kept rising to meet his income and one day he just had enough. He moved to the islands where he would move from one island to another as a dive master. He didn't make much but his needs were few and he made lots of friends. Plus he got to spend his days doing what he loved (diving) and his nights in paradise. He hadn't worn a tie or a pair of socks in five years and was perhaps the happiest man I've ever met.

 

And yet you make fun of Buck all the time.

 

That's just because of Buck's tiny penis.

 

Haven't you been making this post for like 5 years now?

 

Every day, I get a little closer.