Arriving by Air
The airport in Havana is not what you would call "visitor friendly." As a buddy of mine says, the motto is "security time is all the time." Once you arrive, you must pass through passport control. Despite what you may have heard about the Cubans not stamping U.S. passports, it's purely discretional. Just because you ask the inspector not to stamp your passport does not mean that he or she has to comply. Not that it makes much difference; if you think that Uncle Sam needs a stamp in your passport to know you were in Cuba, you are mistaken. There's a thing called a flight manifest, with which all airlines must comply.
When you check in for any international flight your name and passport makes up that manifest, and that information is available to those who ask for it no matter where you may fly from. Why do you think that when there's a plane crash somewhere that they know the number of people aboard and their nationalities within minutes?
Arriving in Havana on a tourist visa means that you are there on vacation. It used to be that all you had to do was tell the inspector the name of any hotel and he or she would let you pass. Recently, as part of the crackdown on private-home rentals, the Cubans have required that you have a voucher in hand for a hotel for each night you are going to be in Cuba. They even set up a desk in the airport for Havanatur, one of the official tour operators. If you do not have a hotel voucher for each night, before you are officially permitted to enter Cuba, you have to go to the Havanatur desk and pay for a hotel. The trick is to book a ticket for two or three nights, pick the cheapest hotel you can (not easy), and then change your ticket later for the true length of your stay.
While you're in Havana many people will try to rent you a place to stay; unfortunately, the closer you get to the older part of Havana, the more likely the room is to be in a state of disrepair and in a cramped building. The best private rooms and homes are in the Miramar neighborhood, where the art deco homes of the 1930s and 1940s are more like museums than houses.
The customs inspectors in Havana are some of the most thorough on the planet. If they select you to have a baggage inspection they will search every bag, every pocket, and every container. They even search the seams of your luggage, so do not bring anything in you don't want anyone to find. I once traveled with a friend who had a small unmarked bottle of hydrogen peroxide. When officials asked what it was, he explained it could be used to gargle with if you had a sore throat.
"So you can swallow this if you have to?" asked the inspector.
"Why sure, I guess so," said my friend.
"Swallow it then!" the inspector commanded. And my buddy did.
People may tell you to bring medicine, tampons, chewing gum, clothes, etc., to give as gifts, but I have found that in Cuba three things are most sought after: the U.S. dollar, followed by the two other universal currencies, Marlboro cigarettes and Johnny Walker Red.
Having a private car in Cuba is rare. Often those who have cars are doctors, members of the Communist Party, or other professionals who work in some sort of high public function. Sometimes the driver of a gypsy cab (a car owner working as clandestine cabbie) is a doctor "on his way home" or a plain clothes policeman. Most likely, though, you will find the car was "borrowed" or "rented" from such a person. One thing is for certain: these private cars are not supposed to compete with the official taxis authorized by the government. Nonetheless, there is nothing like driving around Havana in the back of a '55 Dodge, and thankfully it's still tolerated to a perpetually fluctuating degree.
I used to have a driver whom I would call to meet me at the airport, but that became too difficult for him (and expensive). We decided instead that I would just meet him a block away from where I was staying. He would park and then jack the car up as though he had a flat tire (a common trick) so the police would not hassle him for trying to pick up rides.
Most gypsy cabs have windows with dark tint so no one can see inside. If you're stopped, it's good to have a couple of cigarettes and a couple of bucks folded up real small in your top pocket. The standard story is that you are from Miami on a familyvisit. The cigarettes and money are to make sure that your story is easier to swallow.
If you can, try to hire a car for the day, and arrange the price up front. Make sure you haggle but don't grind the guy too bad; $50 a day is a good benchmark. If you plan on driving a lot, you may also be expected to pay for gas. Often the gas is locked in the trunk (to avoid theft), and taken out one gallon at a time, and put in a makeshift gas tank found under the hood.