This was my first trip to Cuba, but I'd like to offer some tips based on our experience and that of some of our friends:
- If possible, go to a baseball game: we traveled into Matanzas to see the Cocodrillos in the semi-finals and it may have been the loudest and craziest sporting experience I've ever had. They have tourist seats that are cordoned off right on top of the away team dugout, but you can sit anywhere. The games are free for Cubans and 3 CUCs for tourists. There was a drum and horn section, and a LOT of air horns.
- Eat out: A lot of people told me that the food in Cuba is terrible. That may be the case if you are constantly eating pizza and hamburguesas from the resort, but we had incredible meals when we ate at Cuban restaurants (try El Mojito if you're staying in Varadero).
- Hire a driver: you pretty much have to cab everywhere outside of Varadero, but that's not necessarily a bad thing. We took a car to Matanzas the second day we were there and the driver became our guide for the rest of the week. He escorted us to the baseball game and toured us through Havana. Which brings me to my next point...
- Tour Havana on your own: Old Havana is probably where you'll want to spend most of your time. Go to Revolution Square, the fort, and the Capitol building. Then, get dropped off. It's easy to do a walking tour or just wander through old Havana. You might get hassled a bit, but likely far less than you would if you were with a tour group. Plus, you can get into restaurants and tourists spots a lot easier and you're not limited by time.
I had heard mixed reviews of Cuba before we went, but I really loved it and would definitely recommend it!