3 months in the Caribbean - Where to base ourselves?

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A year and a half ago, my boyfriend and I quit our full time jobs to go freelance (IT industry) and travel the world. Since then we've been bouncing around spending 3-6 months in various locations. (The Philippines, Thailand, Bali, Malaysia, and most recently Costa Rica). We're planning to head to Honduras next (and possibly a bit in Belize), but after that we're not sure where we should go.

We haven't really considered the Caribbean, until now, due to it's perceived high costs, but since we're not sure where to go next, I thought I'd do a bit of research, and see what kind of costs we're really talking about.

The problem is I don't know where to start. There are lots of possibilities from Bermuda, to the Caymans, to Bonaire and Curacao, I can't decide where to start looking.

We'd like to spend 3 months somewhere, and rent a furnished apartment/house. We like to cook at home to keep costs down, so being close to a grocery store is ideal. We like small town island life, but need a few good bars and restaurants to keep us entertained.

The most important thing however is that we need a decent reliable internet connection, and can't rely on cafes and restaurants. They're a good backup, but we work a minimum of 6 hours a day 5 days a week, and can't be sitting in a cafe everyday. I know the islands have frequent power outages (much like everywhere we've been it seems) but we can deal with that, as long as we're not talking days and weeks at a time.

Budget wise, we'd be willing to pay up to $900-$1000/month in rent, (utilities included) and another $1500 for food, booze and activities. Diving would probably have to be additional, but if we could get in a dive or 2 a week in that budget, that would be great.

I know this is kind of a broad question, but I'm just wondering if this is realistic in the Caribbean, and if so where should we begin our search?

Thanks!

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