I worked remotely for a US based software company on the island of Guadeloupe in the Caribbean for most of 2010 while my girlfriend taught there. It was pretty

I worked remotely for a US based software company on the island of Guadeloupe in the Caribbean for most of 2010 while my girlfriend taught there. It was pretty fantastic, The major challenge was as you might expect... connection speed and stability. As you can see from the map most of the islands have fiber jump offs: http://www.connectinghaiti.com/ http://www.connectinghaiti.com/ but the challenge is in how local governments regulate them. At the time that I was working there the very best internet money could buy as a consumer on our island was only about 4 MB which made certain types of things challenging. luckily I worked with a company that was in love with the idea of distributed teams, so they maintained virtual desktops in the United States that people could connect to do things where the slow bandwidth might mess with something important. Mainly things like executing code with our main data warehouse. Another thing that you run into is access to a good consumer electronics market. If I am trying to get setup to work from home in the US it is easy to solve little problems, I can order things online and get them the next day or if I am impatient I can go directly to the store and buy usually exactly what I want to solve the problem. This won't be the case when you live on a small island, stores hit the general notes but if you are looking for something specific that you will know will solve a problem you may be disappointed. This can also be a risk if your primary machine goes down. I am not saying you should pack for the trip like a survivalist, but its important to think about things that could go wrong ahead of time so that you can plan for contingencies. Again my work being more than accommodating direct shipped me several items that I needed and pulled my ass out of the fire. As to quality of life it can really be amazing. My company generally operated on Pacific time since all of the senior managers lived in California, as a result I would usually get up in the morning go to my surfing lessons lounge a bit then come home at around noon and start working. As I sit typing this I am really starting to wonder why I ever came back to the US..... ::opens new tab to look at plane tickets::