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Off-the-Beaten-Path "Perfect" Beach+Culture+Adventure+Nightlife Island

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We're a young(ish) couple on a budget (~$1000-1500) looking to vacation in the Caribbean for the first time. We will be flying out of NYC in late December/January.

We want:

-to be nowhere near an all-inclusive resort...ideally, we want to stay in a cheap homey place run by friendly, low-key people and inhabited by the same. We can cook and wouldn't mind trying on our hand at it on vacation.

-empty (or semi-empty) beaches good for swimming, reading in the sand & snorkeling. My boyfriend also loves body surfing but not a must.

-music and food...we would like to be able to go at night, get a good drink and eat fresh food, listen to live music, dance, mingle with the locals and like-minded vacationers

-stories...we would love to be somewhere where the people can, and more importantly, want to talk to us about their country, where there is a visible history that we can visit; colonial architecture and people deriding colonial architecture, ancient ruins, all of it.

-to walk...everywhere; forest hikes, waterfall hunts, city streets to buy fruit in markets, horseback rides anywhere...during the day, we would like to explore as much as we can.

Some islands I've looked at that seem to fit the bill: Vieques, Tulum, Dominica, Isla Mujeres...but how to choose?! All the glowing, knowledgeable recommendations you all seem to give so well will be most welcome!

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