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HELP! First-time vacationer to Caribbean in need expertise

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Hello!

My boyfriend and I are trying to plan a trip to a nice beach somewhere to go this December or January (most likely end of January). We both have lots and lots of travel points with Southwest, so ideally we would go somewhere that SW travels to (i.e. Aruba, Belize, Costa Rica, Jamaica, Bahamas, and DR). However, it's not a total must if we can find another great option.

We want to try to spend less than $1K each, including flight, food/drink, accommodation, activities, everything (I know, we're cheap). Ideally 4 nights, since it's hard to take off work. We'll be heading from Washington, DC.

We are totally new to vacationing in the Caribbean and have no idea what to look for. All-inclusive? Airbnb? Basic hotel on the beach? WE HAVE NO IDEA. We are open to anything. The only thing I would like us to have is something that is easy, which is why we are leaning towards all-inclusive stuff. But having never done an all-inclusive trip, I'm wondering how to know if it's worth the price (aka is it better/more fun to cook for yourself/have the freedom to go out to different restaurants, etc.?). If you have any suggestions based on your own experience, please share!

I am also looking for something that can offer a variety of activities, including snorkeling, scuba diving (at an affordable price), maybe a place that can offer scenic hikes/other cool stuff like that (I like hikes because they're free!), paddle boarding, etc.

In addition, I think it's important that we go to a place that is unique, and is unlike something we could just find here in the continental U.S. I'd like to go somewhere that has a cool town that we could explore and meet local people. Otherwise, I don't see the point in dishing out the time/effort to go somewhere seemingly "exotic".

I know this is all very vague, but as you can see, I just need some general advice here... HELP!

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