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Cuba can be a GREAT experience, even if all you want to do is sit on a beach. Have been a few times over the years. Here is what I would say . . .
Cigars: Do NOT buy them on the street. ONLY purchase from the official retailers. If your hotel offers it, DO try one of the handrolled cigars on offer. Some of those guys are true artists.
Rum: Lots of good ones to choose from, so sample a variety and bring home the one that suits your palette most.
I will second the idea of getting out and about and away from the touristy things (though I HIGHLY recommend the dolphin experience near Holguin). The people of Cuba are very friendly, educated, and enjoy talking about their country with tourists.
Food: Depending on how delicate your system is, make sure to try the local cooking. It is a treat
Thank you all for this advice. I was previously warned about the cigars. Since it's all state owned, there really aren't any 'deals' to be had. The other advice I've gotten concerns restaurants. Apparently the best ones are paladars (private homes). I go at the end of November and look forward to it.
I was in Cuba about 4 years ago. I found it to be very safe - no guns and no drugs - despite the poverty. Things in Cuba may have improved since then, but pretty much everyone I talked to in Havana asked me to give them money - not to buy booze or drugs; rather they really need to money to get by. I found the people to be very friendly and open, and they really seemed to like Americans despite the embargo. See if you can get to a baseball game - Los Industriales are the Yankees of Havana. The music also was fantastic and it begins around noon in the cafe's. I saw all kinds of live music - everything from Cuban jazz to an accapella band singing classical Cuban folk songs. It is definitely worth checking out the "Las Vegas" style show at the Tropicana or at the Hotel Nacional. They last about 2-3 hours and have an orchestra, dancing, singing, showgirls changing costumes. Also be sure to have a look at the monument to the USS Maine which is located along the Malecon - part of the monument are the guns which were salvaged from the actual ship after it sank. I found the food in Havana to be not so great - not because they cannot cook, but because it is tough to get a lot of ingredients at a reasonable price. I ate at a few palleadores (a restaurant that someone opens in their own home - most of what they earn, the government takes in return for a license to have the business). In upscale hotels or restaurants, however, the food was really good. Havana was also very safe despite lack of working street lights - and believe me it gets dark at night. Security was also good and lots of police around. Another highlight was the camera obscure - a contraption built sometime around 1900 - through a configuration of mirrors and lenses, it creates a very high definition picture (it is actually a reflection, not electronic). It is on a high floor of a building in the old part of the city and they can point and move the lenses to focus in things all over the city and it gets projected onto a bit screen that looks like a satellite dish.
You are lucky to be going at this time - the embargo is about to be lifted and there will be an invasion of money and businesses from the US - MacDonalds, Pizza Hut, and other companies will be going in and turning downtown Havana into a big shopping mall. Instead, right now it is like stepping into a time machine - not a lot has changed since Castro took over in 1950. Have fun and please write a report when you get back!