We'd like to spend around $1500 for flights (that's for two people) and another $1000 for accommodations. We'll be flying from Chicago and we aren't looking for an all-inclusive type vacation. What we are looking for is warm weather, nice beaches, lots of cocktails and delicious fresh seafood, and a place where we can do some exploring. We spent a week in San Juan, Puerto Rico last year and loved it - so something like that would be perfect. We're in our early 30s and pretend that we still like to party like rock stars, but in reality we don't see the other side of midnight very often.
Anyone have any ideas?