Bigdog – Good point about bringing stuff to give away. I’ve heard that the Cuban people really appreciate it.

Cyclezealot – I agree with your points about international travel. I have heard about large fines for traveling to Cuba without permission. I happen to have a little insight into that.

Of course, it would be safer to travel to Cuba with permission from the state department or by fitting an exemption. I’m sure an organized bike tour, assuming it is a U.S. company, would take the right steps to get permission. But for those who don’t fit an exemption or travel to Cuba without permission, here’s some info.

I worked for U.S. Customs for several years. People do get fined for traveling to Cuba, but it is usually those who are smuggling Cuban goods (i.e. 20 boxes of cigars hidden in secret compartments). If you use your passport to travel to Cuba, it can be revoked by the state department. Cuba varies their treatment of U.S. passports. Half the time I worked in the airport, Cuba did not stamp passports at all. Then they started stamping passports with a small “D” on page 16. I don’t know why they did it, but I saw it get a few people in trouble. I hear that they don’t stamp them at all now – I hope that is correct.

U.S. Customs has access to the passenger manifests (including booking information and itineraries) of all airlines that enter the U.S. – this includes foreign flights of those airlines. Customs has analysts dedicated to researching itineraries every day. They mostly look for drug/terrorist traffic. But on a slow day, they may look for plain old Cuba travel.

A person entering the U.S. could be examined for many reasons – random exams, Inspectors may interview a person and decide to do an exam, there may be a special smuggling trend they are watching for, analysts may alert Inspectors to a particular person, etc... I remember being told several times to check out a particular passenger because they had been to Cuba. Most of the time, my sups just wanted me to make sure that the passenger was not bringing merchandise back. Many times I found Cuba travelers just through my own interviews of passengers.

Your chances of being examined are pretty low. It is estimated that Customs only catches 5% of the drugs imported into the U.S. So your chances of getting thru as a traveler to Cuba (assuming you are doing nothing else illegal) are pretty good. Much of it depends on where you enter the U.S. Miami, for example, sees tons of Cuba travelers. I hear that they are pretty much not harassed at all. On the other hand, if you fly into a smaller international hub, you may run into a bored Inspector looking for any violation to chalk up marks on their record.

Merchandise from Cuba is illegal unless you travel to Cuba with permission or on an exemption (and there are strict limits in those cases). Cigars and rum are the main focus. Tourist items, handicrafts, art, etc are largely ignored unless they are being brought back to be sold. If you are caught, how the merchandise is handled varies by location. Where I worked, a box or 2 of cigars was simply destroyed in front of the passenger. But some locations would enter a seizure record in the Customs computer system (TECS) for even 1 cigar (Newark was notorious for this). If items are “seized” there will be an enforcement record on your name/SSN/passport number. This makes the chances higher that you will be looked at in future travels. Plus, you may be fined if a seizure record is input.

Like I stated above, chances are you won’t get caught. Or if you do get caught, not much will happen. In light of that, this might be overkill...but for U.S. citizens who travel to Cuba without permission, having worked for U.S. Customs I have 3 main points of advice:

First, don’t bring much back. If I remember right, people who go to Cuba legally can only bring back $100 of stuff, including no more than 1 box of cigars. If you go illegally and bring back a ton of stuff, you are asking for trouble. If you get caught with a few tourist items, chances are they will recognize you are not a threat and let you go without any consequences. If you get caught with a bunch of boxes of cigars, you are probably looking at a fine and a record in the computer system. Anyway, Cuban cigars are popular here because they are illegal – they are good, but I’ve had better Dominican and Honduran cigars. Personally, I’d prefer lots of pictures as opposed to a few cigars.

Second, buy your ticket to Cuba once you are in your intermediate city. For example, fly Continental/American/[insert name of U.S. carrier] to Cancun/Toronto/Mexico City, then buy a ticket to Havana on a foreign carrier like AeroMexico/Air Canada. This makes it harder for Customs to track your travel. They can still track it, but they have to look at 2 airlines on 2 different systems and put it all together. I knew analysts who would do this. But now they are probably too busy tracking terrorists and drugs to waste time on that. Travel in late spring or early summer will offer even more distractions to the analysts because that’s the coke and heroine season. If you book the entire trip on a foreign carrier, it is super easy to track the Cuba leg.

Third, don’t lie in the unlikely case that you get caught. Inspectors get lied to all day, and they get really sick of it. If you are caught, fess up and the Inspector will most likely realize you are not a threat and let you go. If you keep lying with the evidence spread in front of you, chance are the Inspector will push the issue.

Good luck to anyone who goes. I would love to go to Cuba, cycling or not. I hope to make it there before the U.S. eases restrictions, and Havana turns into a huge party center for recent high school grads (another Cancun?).