This from a while back, but perhaps of interest:
The American Conservative, December, 2007
On Havana's malecón, the seawall that parallels the shore, the waves roll in and hit the sudden obstacle, sending towering explosions of bright white spray far into the air, occasionally soaking the unwary pedestrian. Across the highway that follows the malecón is a cheap open-air restaurant, the DiMar. A steady breeze from the sea pours across the tables. A tolerable shrimp cocktail, topped with mayonnaise, costs a few bucks. On a couple of evenings I drank a beer there, watching Cuba go by. It wasn't what I had expected.
Unlike many gringo tourists, I was legal, having gotten a license from the Treasury Department. Without a license travel to Cuba is illegal under the Trading with the Enemy Act of 1917. Why Cuba was my enemy wasn't clear to me. Nor was it to the Cubans.
I had inadvertently neglected to tell the authorities that I was a journalist — I hate it when that happens — so I was not in a position to ask probing questions of officials. But then I didn't want official twaddle. I wanted to wander, take cabs down the coast, just look at things. And did.
I was pleased to find the old part of Havana both charming and reasonably well preserved, especially around the convent of San Francisco. The latter is of course a museum now, as God knows we mustn't be religions, but it is in good shape and breathes a moody solemnity. I tried to imagine the stillness in times before the motorcycle. The narrow lanes around it were closed to cars, making it pleasant to walk among the shops.
The country is poor and run down, and itself almost a museum. Sitting in the DiMar is like visiting the Fifties. The American embargo makes it hard to get new cars, so many Cubans still drive cars from 1959, the year of the revolution, and before. Some sport jazzy paint jobs, and others don't. It was remarkable to watch the rides of my adolescence go by, charting them mentally as one did in 1964-'54 Merc, '57 Caddy, '56 Chevy, on and on. Around me the other customers, down-scale Cubans in all shades of nonwhite, laughed and chatted.
They are an accommodating people. On my arrival they spoke a truncated Spanish hard to understand — "Cómo etáh uteh? Ma o menoh." — but they made an intense national effort to improve their clarity and by my fourth day they were comprehensible.
Cuba doesn't fit its sordid image. It is most assuredly a dictatorship, yet the police presence is much less than that of Washington, and such cops as I saw had no interest in me. It is not regimented. Havana does not feel — well, oppressed — as Moscow did during the days of the Soviet Union. Mao's China it isn't.
The island certainly isn't dangerous to anyone. Somebody said that the only communists remaining in the world were in Cuba, North Korea, and the Harvard faculty lounge. I do not know whether Harvard's professoriate thirsts for godless world hegemony, though the idea is not implausible, but it is absurd to put North Korea and Cuba in a category. Pyong Yang has, or wants, nuclear arms, and has both a huge army aimed at South Korea, and a habit of testing ballistic missiles of long range. Cuba has little military and no one to use it against; from an American point of view, the Cuban armed forces are about as terrifying as George Will with a water pistol. It has no nuclear arms and no signs of wanting any. It is not a rogue state. It is a bedraggled island of pleasant people who need more money.