Caribbean - Short family xmas-ish trip to Caribbean?

Hey all,
My wife, sister and mother want to get together for the holidays and were thinking of going somewhere warm. We were thinking the Caribbean, but none of us have ever been there, so I'm looking for guidance on islands. Once we have that narrowed down, I imagine the "UTFSE" tactic will work ;)

We're all drinking people, so we're looking for somewhere with some nightlife, no where seriously dangerous, and the budget is around $400-ish/night for 2 rooms. We've been all over the world, so a little hassle is not a big deal, we're really just looking for swimming, chilling, and a little nightlife. It's going to be for 4 days, probably the 15-18th of Dec. Anyone have experiences they want to share?

Thanks!
matt.

Most of my Caribbean visits have been via cruise ship, so I haven't been around late enough in the day to really experience nightlife. However, the nightlife on cruises can be a lot of fun if you pick the right ship.

That being said, I really enjoyed Playa del Carmen. Not really the Caribbean in the traditional sense, but definitely warm! Lots of accomodation choices, ranging from all-inclusives to standard hotels. Nice beaches, incredible pools at some of the properties, plenty of tourist police to keep you safe, and enough to do if you choose to do more than chill. I like the nightlife atmosphere in PdC better than Cancun, although if you stay in PdC it's incredibly easy to get up to Cancun for the night either by taxi or organized bar hopping trips. If you choose this area, I'd highly recommend staying in town - for example the Royal PdC all-inclusive is walking distance to a lot of the bars and clubs, and a short taxi ride to the rest.

We've got a trip planned to PdC in February, so we're looking for something different on this one. I do agree it's a great place though :D

Drinking, nightlife, not seriously dangerous, $400ish for rooms.... Sint Maarten? San Juan?

Drinking, nightlife, not seriously dangerous, $400ish for rooms.... Sint Maarten? San Juan?+1

SXM and SJU would both be top of my list as they meet your criteria and you can get there with a direct flight, which means less time wasted in airports for a short trip. You could also consider GCM (lots of dining choices), or MBJ (although your dining options will be less diverse).
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13F

I've been looking into SXM but according to tripadvisor and AMEX vacations, most of the island is booked up for xmas. Drat.

I've been looking into SXM but according to tripadvisor and AMEX vacations, most of the island is booked up for xmas. Drat.
Is AMEX the only booking option?

What about SJU?