Barbados

Eating/Drinking:

Oisten's Fish Fry- go on Friday night, you can eat there and then stay for the dancing/drinking
The Cliff - expensive restaurant, but can go just for drinks, has an amazing view and they light up the water so you can see the big fish swimming at the shore
Zaccio's - pizza place
Harbour Lights - one of the crazier nightlife options, check before you go to make sure they are open that night. I think there's a dress code too
Other nice restaurants (some are pricey!): Tapas, Cin Cin, Champers, Lone Star (also good for drinks, celebs stay here), The Beach House, Cafe Sol, Jumas

Mullin's Beach - popular beach with a fun beach bar/restaurant. Gets a little crowded with British tourists though. You can walk down the beach south to Gibbs Bay which is my favorite beach and no one is ever there.
Animal Flower Cave- on the northern tip of Barbados, you can sometimes see whales and there is a beautiful cave you go into and see out to the sea. Very quick cave tour, but you can have drinks or eat outside after
Second Street/First Street in Holetown - there are bars in this area, good nightlife
St. Lawrence Gap - nightlife and restaurants
Speightstown - cute city area north of Holetown, you can go without seeing it though
Other activities - you can rent paddleboards, surf on the east coast, take a boat to snorkel with turtles, there's always guys zipping by the beach with jet skis that you can rent on the spot, if you golf there are plenty of courses (Green Monkey, etc)

Wear bug spray!
They accept USD almost everywhere but give you back change in Bajan
Try the Bajan style hot sauces
West coast has the best beaches, stay over there
Cabs are a little expensive, and I have the name of a driver if you need it. I took the local Bajan bus but some people think it is a little scary.