Quote from Anekdoten:
If you want anything close to civilization in the Caribbean, I have to say Puerto Rico.
Anek
He said low crime. I lived in PR for two years. It's crap. Electricity is turned off all the time (they tried to turn it off to prevent fires in a tropical storm several years ago and they couldn't figure out how to turn it on again - for two weeks). Water goes out, etc. Crime is miserable (drug related mostly) and the government is a joke. Also, despite it being a US Territory, most of the general population couldn't speak a word of English to save their life.
The person who mentioned Haiti had me laughing. Yeah, that's real safe! Same with the Dominican Republic. LOL!
I think Aruba would be a good call. Doesn't get hit very often by tropical cyclone activity because it's so far south. It's a beautiful and fun island, with about 550,000 people, 450,000 of which are seasonal and tourist. It's also a rather dry climate, not rainy and wet with billions of mosquitos.
I'd be curious to understand Aruba's tax laws.
