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Anonymous
Depends on where you live. If you're near Canada you might be able to score some cheap charter tickets. I went through Cancun because Cubana tickets were (at the time, early 2000) $200 round trip, payable in cash, which was perfect for me. Getting to Cancun is pretty cheap as well due to the number of tourist flights. Note that Cubana has a pretty bad safety record. On the bright side, they fly some very interesting Soviet era equipment which you may not get a chance to see anywhere else outside of Russia, Eastern Europe, and parts of Africa.
Rumor has it some countries, such as Jamaica, DR, and possibly Canada, have special immigration stamps for passengers arriving from Cuba. If you're a US citizen that could be bad for you.
There is an apartheid system in place to keep the locals and the tourists apart. It's not hard to violate this system, but expect to be questioned by the authorities at every step. As long as you don't do anything really dumb like try to buy drugs, you probably won't suffer for your efforts, but you may cause headaches for the locals with whom you fraternize.
Hopefully you can go with a female friend so you're not constantly hounded with offers of Cuban hookers. You will be followed around by Cuban cops if you choose to roam the city freely. You will constantly be asked for gifts by everyone.
It was not what I expected at all (I read some travel books about Cuba and believed everything that they said), but I don't regret going.
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