We found Key West to be the closest thing to the Caribbean without leaving the US. The weather was great (although very hot in August), lots of history, pirate stories,haunted locations,great museums & art galleries, reasonably-priced restaurants,entertainment & of course, great sunsets! I Most of the entertainment options were geared toward adults so I wouldn't recommend it so much for families with small children. My wife & I really loved it and it's a great place to just "chill out".