Next Caribbean Destination?
 

Hi all. I've now been to the Caribbean Islands 4x: Punta Cana & La Romana in the DR, San Juan, and most recently, Aruba. I enjoyed my time at all four locations, but the most in Aruba and San Juan as there were things to do outside of the resort and it was fairly easy to get around in a rental and public transportation.

Where else can I go where I can have the same thing? I am open to AI but i'd prefer the ability to choose from a variety of restaurants in town even if i have to walk or take a shuttle or something. i'm not a foodie so restaurants similar to regular american chain restaurants would do. Budget-wise, i'd like to stay < $2,000 for two including air & hotel flying out of DC.

Check out the Riviera Maya, Mexico. The Playa del carmen area would suit your needs. Lots of AI resort to choose or smaller boutique resorts right in town.
You could visit Mayan ruins, zip line, snorkel, etc.

I don't have a lot of Caribbean travel experience, but a friend and I spent 5 days in Isla Mujeres and absolutely loved it. There's a small town with tons of great restaurants and margaritas are 2x1 everywhere, all within walking distance.

Isla is considerably cheaper than what you're looking to spend, but that's great because it will leave you $$ leftover for the different little trips you can take. This webpage tells more about the different trips:
http://www.entertainment-plus.net/tours/ (We used this transfer company and were very happy with their service and their prices).

If you have any questions or are interested in seeing our trip photos, let me know. :)

Jess

Cozumel might be an island you'd enjoy.
And it's an easy ferry over to Playa del Carmen if you crave more bustle and shopping and eateries, nightlife. (not that you can't find that in Coz.)
And if you want even more, it's not far from PDC to Cancun.

Check out Applevacations.
In your price range, there will be lots of 5 day trips, and possibly some 7 day.