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25 year old guy from Chicago looking for solo getaway suggestions

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Hi all!

I'm Bryan. I'm 25 and live and work in Chicago (Illinois native).

I have been experiencing a lot of changes in the past year, including a very unpredictable, high-stress job in the technology space. I am looking to plan a last-minute, solo trip to help myself decompress, unplug a little, and set some goals for 2014. I have never traveled alone, but am excited to do so.

My budget for this trip is approximately $800-$1,200.

Here are my criteria:

-Not Mexico, I've been there several times

- Warm and sunny (Chicago winter is brutal)

- Relaxing, but not isolating (i.e. I don't want to be going back to a fancy room by myself at some all-inclusive resort. Rather, I'd like to visit somewhere where everyone around me is going about their day-to-day life.)

- Minimal-moderate language barrier. I speak enough Spanish to get by in most places in Mexico, but if no one around me speaks any english at all, that may not be so great.

The picture in my head:
A small, yet not desolate, island somewhere south of the US. Local folks selling fruit on the streets. Small cafes run by 2 people. Groups of older gentleman sitting in circles rolling cigarettes and BS'ing. Sun, sun, and more sun.

Thank you for any input - I would really appreciate the insight of the Fodor's community on this one!

Best,
Bryan

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