Cuba Traveler's Information for US Citizens

Americans are for all intents and purposes, not allowed to travel to Cuba.

Heavy fines are being imposed and at a much greater frequency under the Bush administration. If you yet didn't, please check out the OFAC website  OFAC Website

OK fine ... how do I go to Cuba? (for US citizens)

"When unlicensed travelers go to Cuba from the US they normally have to go through a third country. You will frequently see this referred to as the "Gateway" on various boards. The most common gateways to Cuba for unlicensed US travelers are Toronto, Montreal, Nassau (Bahamas), Cancun and Mexico City, and less frequently used Santo Domingo (Dominican Republic) and Montego Bay. In my opinion Mexico and in particular Cancun are the gateways that offer the least risk of detection I say that because:

** Unlike Canada and the Bahamas, a traveller leaving from Mexico does not pre-clear US Customs and Immigration. You will not clear Customs/Immigration until you arrive back in the US. In Canada and the Bahamas you will go through US Customs and Immigration at the airport in Toronto, Montreal or Nassau.

Cancun is the most popular destination for US tourists in the Caribbean. There is absolutely no reason why US Customs/Immigration would suspect you have been anywhere else but Cancun.

You can book your hotel and flight in/to Cuba through the Junky websites with your US credit card without any risk. 
Your credit card receipt will state nothing about Cuba or whatever.

You should take the following steps in traveling back/forth:

- Enter Mexico from the US

- Mexico does not stamp passports on exit, although you will need a passport to enter Cuba.

- Cuban Immigration does not stamp the passport at the present time, so do not worry about a Cuban stamp.

- When you arrive back in Mexico from Cuba you will probably have to present your passport. The entry stamp that is placed there should be the only stamp you receive on your trip. Some people recommend presenting the passport with a $10 bill inside to avoid the Mexican entry stamp.

- After you arrive in Mexico make sure you strip all HAV luggage tags from you checked baggage.

- Throw away your Cuban tickets, boarding passes and any other paper evidence of your Cuban trip.

- Do not list Cuba as a Country visited on the Customs Declaration form.

- Do not bring back any high profile Cuban souvenirs like cigars, rum, t-shirts.

The fine by the way if you are unlucky or careless enough to get caught can be negotiated down to $1000 or less.

Travel Documents For a US citizen

Passport (US related)
Make no mistake about it ... you need a "valid" passport to get into Cuba. Whereas in some countries you can get in with a US birth certificate (Mexico, Canada) or even an expired passport (Bahamas), you will NOT be admitted into Cuba with these credentials. Make sure its valid and current.
Passport Stamping - Fortunately, the Cubans know that returning to the US with a Cuba stamp can be trouble if you're not there with a General or Specific License from OFAC. It used to be that if you slipped the immigration official a $5 or $10 with your passport, it was no problem. However, now there are posted signs in the Immigration Department discouraging such practices. 
Either way, the best thing to do is smile, say something nice then ask them in Spanish to please not stamp your passport. "Por favor, no empuje mi pasaporte" should do fine. This is still no guarantee that they won't however.

Holy crap ... they stamped my passport! (US related) 
Immediately wire home and have them send you enough money to hide out in Cuba for the rest of your life!! You will need to ... just kidding.
If you check the OFAC papers (see link on navigation panel), I'm sure you'll probably find a sanctioned way to go and not have to worry about it. If not, the chances of actually being assessed a fine are pretty remote anyway. 

If you feel the need to bypass the system and go anyway, well ...
CAREFUL: Lying to an Immigration Official is a Federal Offense. If you lie, you'll probably get through. Then again, if they decide to question you, well ...
If you tell them the truth, they'll probably just wave you on through. However, if not, read the above OFAC section.
If you get through, there's always that stamped passport you have to contend with. Again, the absolute best way to go about it is under the OFAC guidelines. A little reading can go a long way.