On your way home from Cuba, the same rules generally apply. If you have nothing to be nervous about, you shouldn’t have any problems. In Cuba, you’ll go through a departure sequence at the airport, which will include depositing your checked bags, then paying your $25 departure fee. You will be cleared by a customs agent, who will briefly check your documents and retain your loose-leaf “visa.” This is also the time to ask that your passport be stamped again, if you feel like it. It’s probably a good idea to have it stamped leaving if you had it stamped entering the country. In reality, I don’t think it matters. I would defy anybody to look at my passport for a minute and determine where I’ve been and when I arrived and departed. The stamps are smeared, not in sequence, and generally not very informative. The most important thing is that your passport is scanned in each country, so that information is stored digitally in each country’s database, and can be viewed by any agent. I really don’t think it is anything to be concerned about. But as I said before, if you’ve traveled to Cuba with a license, you absolutely have no worries. Yet I’ve read warnings in various Cuba guidebooks about “making sure your passport is not stamped in Cuba,” and “perhaps you can bribe the Mexican customs agent to not stamp your passport upon returning to Cancún from Havana.” This advice may have made sense 20 years ago, but certainly not today. The new customs stations in Cancún are well-lighted and very public—not the place to try to slip somebody a $20-dollar bill.
If you are flying back to Cancún from Havana, you will clear Mexican customs and (unless you need to stay overnight) go directly to your next airline that will take you back to the states. You will have to clear American customs in the first U.S. city you land in, and not at your final destination. For example, you may be flying on United Airlines from Cancún to San Francisco, but your first stop in the U.S. might be in Houston. So in Houston, you would deplane, pick-up your bags, go through customs, then put your bags back in the system so they will be loaded onto your flight to SFO. It usually goes pretty quickly, but it’s possible that you might be detained a little longer than usual. If that’s the case, consider scheduling flights with a longer connecting time in Houston (perhaps 75 minutes or longer). A better idea would be to try to fly non-stop from Cancún to your home airport.
When you go through customs, you and other Cuba travelers will not go through as a group. You will be in a mass of travelers who just arrived from all over the world. The guy in front of you may have just flown in from Moscow or Madrid. The purpose of customs is to rapidly process recent arrivals, and send anybody with unusual behavior or circumstances to the next level. Americans are increasingly visiting Cuba more every month, so you are less likely to be deemed unusual.
Before you go through U.S. customs, you will fill out a standard customs form. One of the questions you will be asked will be, “Which countries have you visited?” Your answer should be, “Mexico, and Cuba with License #12345 (or whatever number your license is). When the customs agent sees “Cuba” he will automatically think, “Does he have a license? Oh yes—he does.” In most cases, that will be all you will need. Once in a while the agent will ask to see your license, so have it ready to hand over. (He may make a copy of the front page or the entire document, but this is rare. Every license is unique and looks different, so the main thing the agent would look for would be that your name matches your passport, and the dates you traveled in Cuba are concurrent. He will not be able to validate your license or determine if it is appropriate for your travel. He may ask if you acquired any items in Cuba. You should have them listed on your customs form. Be sure your license has a page that refers to the regulation that allows licensed travelers to bring back certain objects, such as artwork and music CD’s. I always carry an extra copy that I can give to the agent, because most of them don’t seem to know about or remember that particular regulation. Last time I checked, there were eighty pages of customs regulations involving travel to Cuba, and various sections of these regulations are changed on an irregular basis. So it is reasonable and helpful for you to give the agent a copy of the page which describes what you can bring back. Always be courteous and respectful. Don’t start ranting about your right to travel or how unfair the laws are. The agents already know this. Similar to IRS agents, their job is to enforce a bizarre set of irrational laws and regulations patched together by our increasingly dysfunctional and despised Congress.
If the agent is new or isn’t sure what to do about your Cuba trip, he may refer you to the next level of security. It’s not a big deal. You will probably be asked to open your bags and show the items you acquired in Cuba. If you bring back a bottle of seven-year-old Cuban rum and try to claim it is a work of art (which it really is), they will open it, pour it out, have you sign a special document that it was indeed destroyed, and send you on your way. (This happened to me several years ago in Houston, and it was painful to watch.)
If you are flying from Havana directly back to Miami on a charter flight, there will be no question that you just arrived from Cuba. Clearly, you will have been traveling on a Specific or General travel license (you would have needed it to book a charter flight). Many of the customs agents will be Cuban-American, who are quite accustomed to dealing with Americans returning from Cuba. (In contrast to the common belief, most Cuban-Americans in Miami, especially if they are under 40 years of age, do not favor the embargo. Most prefer unrestricted travel and trade, even if they hate Fidel. Recent polls have clearly confirmed this fact, which is not well-known outside of south Florida.) Years ago, Miami customs was known to be especially difficult for Cuban travelers, who were likely to be hassled. Their attitude seems to have changed in the last few years, and the recent big increase in travel by Cuban-Americans has probably helped.
I want to mention that on two of my seven trips from Miami, the same thing happened while I was returning and talking with the customs officials. On both occasions, as the agent was looking at his computer screen after scanning my passport, an alarm sounded and a red light flashed. It was quite dramatic. I was then asked to follow an official to a room, where several other suspicious-looking travelers paced back and forth, or slumped dejectedly in their chairs. In both instances, after about ten minutes, an agent told me, “Mr. Lewis—you can go now.” That was all. I never did figure out why I was treated differently on these two trips, and rapidly processed through on the others. I suspect that while I was sitting there on the “Group W Bench” (if you are older and remember Arlo Guthrie’s “Alice’s Restaurant”), somebody or some thing was probably checking me out to see if I was sweating or biting my nails or fidgeting excessively. I wasn’t. I spent my time reading a book, so they eventually cut me loose.
So what happens if you visit Cuba WITHOUT a license. On my 18th trip, I decided to find out. I researched the situation, and determined what was most likely to happen and how risky it would be. On my return trip, I flew from Varadero to Toronto. It took all of ten seconds to clear Canadian customs, as the cheery agent welcomed me back to Canada. As I left the area, I was greeted by a huge colorful billboard showing the beaches of Varadero and beckoning everybody to come play in the sun. That’s the way it SHOULD be for Americans returning to the U.S.
When you fly back from Canada, you will be pre-screened by an American customs agent in Canada, so I approached him and handed him my customs form indicating the countries I had visited on my trip: Canada, and Cuba. He asked to see my OFAC (Office of Foreign Assets Control) license. I said I didn’t have one. Predictably, he sent me to the next level of screening. The agent looked through my bags and asked what I was doing in Cuba. I said I brought some medical supplies to an elderly gentleman, and spent the rest of my time with friends. He then handed me the dreaded three-page form I’d read about. The print was unclear, the text was slightly slanted, and some words ran off the end of the paper. It asked me to describe where I went in Cuba and how much money I spent. When I was finished, I turned it in, thanked the agent for his service. He said “goodbye” and sent me on my way. That was it. I had been detained about 30 minutes, so if my connection would have been close, I might have missed my next flight. Otherwise, nothing came of it. I read that my three-page form was supposed to be forwarded to OFAC at the Department of the Treasury (headed by Timothy Geithner, Secretary of the Treasury. Need I say any more? He has more pressing issues to deal with.) My form—if it was forwarded at all—was most likely sent to a storage bin in the basement to gather dust, along with all the other thousands of similar documents. In my research, I discovered that the travel laws haven’t been enforced against individual travelers since the last year of the Bush Administration, and probably for a couple years before that. President Obama has directed that OFAC should allow more people-to-people programs, even though some hard-core Cuban-Americans are still lobbying against thi process, and even want it reversed. In my opinion, everybody is just marking time, waiting for the Castro brothers to pass away. I think both governments are simply incapable of normalizing relations, so it is up to us common citizens to act like adults and get to know each other better.