So many great destinations I'm finding the choice overwhelming! Help??
 

My sister has asked me to plan her 30th birthday on a beach somewhere. We will be traveling early November (her birthday is the 7th) and there will probably be between 4-8 people. Our top priorities are: nice beaches, fun/safe town with bars/restaurants, cost...and activities would be nice.
I've traveled to Playa del Carmen, Mexico 3 times already and absolutely love it. The things I love about it are the atmosphere, fun downtown area I feel safe walking around, lovely beaches, and plenty to do (ruins at Tulum, cenotes, etc.). However, a few of the people that are going on this trip went on my last trip to Playa with me...they loved it as well and we'd all be happy ending up there again, but we're also really interested in finding a different locale to check out. There just seem to be so many great destinations in the Caribbean I'm finding it overwhelming!
We've always been able to go for a week, all-inclusive for around $900 p/p (including flights from Chicago). I'd like to keep in the same price range, however we are open to going non-AI. (the last two times I've stayed at the Iberostar in Playacar).
I love to explore and don't believe you can experience a place if you sit on a beach chair at your resort the entire time :) My sister has never traveled outside the U.S. and has never seen clear ocean water, and I'd love to help her experience that!
Any suggestions would be appreciated!

I honestly think you might want to stick with Playa. I don't know another caribbean destination other than Cancun that will give you the nightlife you want other than St. Martin and I would not recommend that.

Barbados is wonderful, but your price is a bit low for enjoying the island. Mexico is always inexpensive. Also you may want to consider Puerto Rico - the air fare there is less costly than to Barbados, so an all-inclusive package there might be affordable.

One great thing about the Playa del Carmen area is that you get so much for so little money. We've been to that area 8 times. Unfortunatly, you are not going to find that kind of atmosphere for your budget anywhere else in the Caribbean. You might look at Cozumel, Isla Mujeres or Pureto Vallarta.

If you're willing to increase your budget, Aruba is our second choice. It's got a great strip area on Palm Beach with beach front resturants in front of the hotels, and a strip section of bars, resturants, shopping and entertainment across the street. Similar to 5th Avenue in Playa in it's own way.

Of all the places we've been to in Mexico/Caribbean, Aruba is the only Carribean location I can think of that reminds us of the Playa area. We are going to Key West in July because of tha same kind of atmosphere, but the beaches there are not that great especially with the oil spill incident right now.

I went to Key West, but that was probably close to 10 years ago! I loved the bars and the town area, and it was a very cute town. But, the beaches weren't great. We tried going to a public beach one day (rocky shore) and there were warning signs up for Portuguese Man o'war so we just went back to the pool :)

I agree with you. We booked a pool side room at a B & B within walking distance to Duval. We probably won't be getting in the ocean. We also plan on going to Dante's. Never seen a resturant/bar with it's own pool. Sounds interesting. We've always been more of a pool person than the ocean anyway.