Sure, its not exactly legal for US citizens to visit Cuba, but hey, toughen up. Where’s your sense of adventure anyways? There’s not much time left to see the old Cuba before it modernizes. Smoke a real Cuban, sip some rum listening to jazz in a social club, or learn about Che in the Revolutionary Museum. One tip from experience, a $20 bill artfully left in your passport will likely convince the customs official to “forget” to stamp it. The Carnival runs throughout the month of August and features local food, dance and art.
Getting there
There's two paths you can take when traveling to Cuba, the legal, and the not-so-legal. If you'd like to go legally, you'll either need to make your case to the U.S. Government or travel on a "fully-hosted trip" which means that you pay a Canadian tour agency in advance, and they provide for everything you need on travels.
About 100,000 Americans choose to visit illegally every year. The cheapest and easiest way is to fly through Cancun Mexico. After you've booked your round trip ticket to Cancun, there are dozens of flights leaving each day on either Cubana or Mexicana airlines. A round trip ticket with the Cuban visa you'll need to buy from the Mexican government will cost you about $300.
What to expect
There's a weird tension in Havana between the ideology of the socialist government and the laid back attitude of its citizens. I often times felt that nobody was working officially; but everybody had something going on underground. People would follow you down the street, covertly whispering "pssst, comida, hotel..." because a. Cuban citizens need a special pass to speak with foreigners, and b. all restaurants and hotels have to be sanctioned by the government.
There were military men posted around the city to enforce the laws. At one point, a nice old woman who proposed that we eat at the restaurant in her kitchen (there are tons of illegal restaurants like this) and she was stopped by a solider who took her to jail for speaking to us without a pass.
After arriving from Costa Rica, we were told stories by our cab driver of how during the "Special Period" in the early 90's when Russia cut off Cuba's aide money how the planned economy just stopped working. There was no gas for cars, electricity was out for 16 hours a day, people lost 20 pounds each on average, and sometimes were reduced to eating "hamburguesas de hierba" or grass hamburgers.
The Special Period forced radical changes on Cuban life and they became expert in urban agriculture and are now world experts in sustainability. Not out of any environmentalist ethos; just to survive.
Things to do/try
Smoke a Cuban cigar, you'll feel like a badass for weeks!
Visit the revolutionary museum, and see a different viewpoint on history.
Eat lots of ice cream, for some reason Cubans take huge pride in their ice cream and its the best I've ever had.
Ride a bus, the buses in Havana are nuts. They often string two or three buses together, and they whip through the city packed to the doors. Not comfy, but definitely an experience.
Eat in a local's house, despite the sad story mentioned above, you'll get the best value and most authentic cuisine this way.
Sip rum in a jazz social club, just keep your eyes peeled, Havana is full of quaint social clubs that will keep your ears and soul happy all night.
Visit the fortress of La Cabaña at sunset. This historical fort has an amazing view of the whole city. Take the tour right before the sun goes down, and you'll catch the cannons being shot off. The fort served as the headquarters of the revolution under Fidel.
