I'm an American university student in a position to work with startup this summer with flexibility in location. I want to travel somewhere I've never been before and stay there for a month and work from there. A nice coastal town would be awesome (I love the sea). Any suggestions about a location? My requirements: high English-speaking population and broadband internet access. A strong dollar:local_currency ratio and cheap flight to/fro helps.
Some places I had in mind: Cape Town, South Africa; Cayman Islands.
Cayman Islands you're lucky to get a pad for $3k, and anywhere you wanna live is probably an expat community home (mid-aged nudist Englishman alert!)
If you're working for a startup, your colleagues will most definitely want you at hand. They might agree to telecommuting now, but if they're really a startup, then they will be screaming their heads off at you over the phone and demanding you come back. If they don't fire you by fax or message in a bottle, that is.
P.S. Stay in the same timezone or suffer the consequences. I am 15 hours ahead of my work zone, and I have days when I just finish a long day at work and feel like a cold beer, even though the clock says it's 8AM where I live.