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My First Vacation Alone & First Vacation in 13 Years

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Yes, I know this is a VERY broad question. I want to take my first solo trip to the Caribbean over Christmas week. I know this is a highly traveled season, thus expensive. It will be the first vacation I've been on in 13 years!

I want to go somewhere in the Caribbean. I've been to Puerto Rico twice and loved it, but want to go somewhere else.

I'm traveling from Chicago.

I don't want nightlife. I want quiet. I want a safe place with a pool and a beach fairly close by. I want good food. I don't want to pay more than $2000 for the hotel and airfare together. I want to be able to walk around and explore the island by myself.

A tall order - I know. Any suggestions for which island and perhaps a hotel or bed and breakfast?

Thanks!

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