I just got back from Cuba on April 7th. I went as part of a humanitarian-ecological mission with Cariibbean Conservation Trust as an American with a Treasury department license. It was a great trip. We were doing a bird census and so spent most of our time in the countryside, which is where the birds are. That means mostly rural environments. The hotels we stayed in were competently outfitted, and the food, while not tremendously variable, was just fine (and in some places, excellent) and certainly far more hearty than most Cubans eat. I found nearly every person I met more than eager to talk to me, even if they spoke no English (I speak very little but some Spanish, French and German, all of which I used.) There were prostitutes in several of the towns, but outside of Havana, I seemed more interesting as a type of wandering zoo animal (I am 6 feet tall with red hair and red beard and very nerdy glasses) than a potential John (apologies to men named John who are reading this.) Once the offer was declined, I was basically left alone. Stared at but left alone.
People in Cuba were poor but not unhappy. There are simple pleasures even if complaining about the government cannot be one of them. And the Cubans seem very able makers of "stone soup" - that is, something from nothing. We saw all manners of conveyance. Bicycles motorcycles pedicabs trucks buses carriages wagons you name it. If you go and rent a car to see the country side, anyone who drives a car and has seats available is expected to help with mass transit by picking up hitchhikers. Tourist coaches cannot do this, so check with the rental car company (Cubacar I think it is called) whether that is allowed for you if you rent. There may be a "tourist apartheid" in effect for tourist rentals.
The best restaurant for my money in Havana is a place called La Guarida, which is a grown up version of a restaurant for tourists that began during the special period (after 1991) when Castro said it was okay for citizens to make a bit of money by serving tourists in their homes. Ask anyone in Havana where it is and they'll show you. Or just tell the taxi you want to go. Reservations required, though you can also wait in line. Great restaurant with tremendous atmosphere in a building that seems held together by dental floss.
Don't take photos of army or police. Don't try to involve people in conversations about politics. Even the most innocuous conversational topics in the area of world events or political criticism may be dangerous for the person with whom you are speaking. You may just get ignored or tossed out of the country, but the Cuban you spoke with may face a long uncomfortable time in a police station and might even lose some of the few rights they have. Follow their lead and don't push the conversation where you think it should go. Don't change money with strangers. Don't give anyone American dollars.
We didn't have any troubles, and everywhere we went was terrific. One of our group carried a suitcase full of pens, pencils, pads of paper and bars of soap. These were VERY appreciatively accepted by teachers and parents. I'd avoid giving directly to children as too much confusion may ensure about your motives, thanks to the immorality of some tourists. We were also warned against children's books as they may be seen as political subterfuge. Other innocent things to bring might be baseballs (Cuba is baseball) or soccer balls.
Try to see Camaguey - it is a great town roughly in the center of the country. Also try to get to Santiago de Cuba (very historic) Baracoa (far east of the country) Guanahacabibes (far west) the Pinar del Rio area (spas, springs, caves) and any place on Isla de la Juventud (off the south coast.) The latter bunch I did not visit (except for Pinar del Rio) but I heard so many interesting things about them, I have to go back. And if you can get to any of the southern mountains (Sierra Maestra for example) go. I understand a large percentage of the mountains are off-limits and controlled by the army.
Note: In 2008, Hurricane Gustav and Hurricane Ike went across Cuba (10 days apart) and smashed a goodly portion of the forests in the mid-to-western part of the island (Gustav) and the eastern-south-central parts (Ike.) With Gustav, winds topped out at over 200km/h, though they don't know how much over because the hurricane destroyed the weather station. The result is that some infrastructure is still broken, so check carefully about hotels, roads and campsites before heading out if you go to that area.
I plan to post my photos later tonight or tomorrow morning. I'll put a link here when I do. In the meantime, you can see my photos of getting my portrait made in central Havana on the steps of the Capitolio by an old photographer and his ancient camera here:
http://www.flickr.com/photos/jornake/sets/72157616643329082/
