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I've visited (but not stayed in) the Hotel Nacional. It's very classy, and it has a great location overlooking the Malecon. It's also reasonably close to Old Havana, which is the most interesting part of the city. Another option would be to stay nearer to Old Havana. It looks like some well-rated hotels are just north of the capitol building. Those put you very close to Old Havana as well as the capitol building and the museum of the revolution, both of which are worth visiting. Staying there would give a very good exposure to what the city is really like. I don't know about places outside of Havana (such as the beach resorts).
The cannon ceremony from the old fort is quite unique ...just watch for pickpockets. I recall a mid-week market in a square just north of Old Havana that's a great place to buy souvenirs.
I'll be returning in early May, but again with a church group and staying in a church in Havana (before traveling an hour SE to the village of Los Palos).
Black dotting. Been meaning to visit for far too long. All of my friends that have been have nothing but positive things to stay. Update us when you get back.
I would avoid government owned Hotels in Cuba and stay in a casa particular. The accomodations are cleaner than even the best hotels (as long as you pick a good casa) and the money goes to the people, not the military. In fact, if you stay only in casa particulars and eat at paladares you have met some of the requirements of "Support for the Cuban People" as your travel authorization/OFAC license. You can book them through airbnb. Staying at Hotels, eating at restaurants, and doing any business with these and other military-owned businesses can theoretically disqualify you from the "Support" travel authorization.
And if you bring back liquor, Havana is about the only place I've seen where the airport duty-free shop has the best prices and availability. Don't bother getting it elsewhere and lugging to the airport. All the cigars you are offered by locals under backroom deals are fakes. Unfortunately, the only way to get real cigars is at State-run shops.
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