Noy... I second Aruba... Was born about 40 miles from there.
Beautiful beaches. Great big surf and lots of secluded beaches deep down obscure sandy roads- watch for herds of goats though. Getting to these beaches is always part of the fun. 4x4 is essential to access.
Tradewinds spin through Aruba pretty intensely so if kite surfing is your thing, you won't be disappointed.
There are a couple of great spots for surfing as well... big swells that can really beat you down (one in particualar in a large cove... let me know if you go and I can figure it out for you- hard to get to, but awesome intenseness)
There are 2 main locations to stay. Hyatt area is great and just north of that you have access to great secluded beaches. The "high rise area" is further south (closer to the airport). The Renaissance hotel in Oranjestaad has a cool shuttle that takes you out to a private island where the flamingos, large iguanas, and Caribbean fish are very well accustomed to visitors = close encounters. One day is enough, but super relaxing and fun.
Lesser Antilles (southern) does have the best weather in the Caribbean... Big storms from Africa generally miss Northern South America coast lines and the Lesser Antilles. Check out "Taste of Belgium" if you go there. Great food and unbelievable import selection of tasty beers.
Definitely a laid back culture with a Dutch and Venezuelan influence. I'm pretty much a beach snob because I grew up in the Caribbean... these beaches are fun... but you have to get out of whatever resort you are at.