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New Traveler: How to Plan an Al Caribbean Vacation in January?

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My boyfriend, his family and I are trying to plan a vacation together. We can travel any time between December 27th and January 5th, and obviously the longer the stay, the better! Our price point is maxed out at $900 per person, and we want an all-inclusive trip, air included. We'd preferably like to fly out of Philadelphia, Washington D.C., or any airport in the PA/MD/DC area.

We do NOT care where we go, we just want some type of Caribbean island vacation! We've discussed Jamaica, the Dominican Republic, etc., and it does not matter; we just want the best deal we can find for our price point.

I've exhausted searches on the web and I've gotten frustrated with not being able to find dates far out enough in our range, and/or with not enough flexible searches for ANYWHERE in the Caribbean. (I don't want to be forced to choose a specific location in a search).

This is the first vacation like this I've ever planned. What is the best way for me to find what I'm looking for? Or, better yet, can anyone point me to deals that match my criteria?

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