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Traveling to Cuba as an American

At the end of 2014, President Barack Obama announced that the U.S would start to resume relations with Cuba after 50 years of Cold War.  At present, in September 2015, the embargo is still in place and Americans are still not permitted to travel freely to Cuba without obtaining permission prior to departure.

How many people actually get permission? I honestly have no idea, but what I do know is that thousands of Americans travel to Cuba annually via another country.  That is precisely what I did and here I will detail exactly what I did to make this trip happen.

  • First, I am a U.S. citizen, I do not have residence or nationality of any other country so I was going strictly as an American.
  • Second, I traveled with my friend who resides in Mexico City, DF and is a Mexican national.  Estefania (Stefy) had no issues, but was worried about being attached to me in the event that I got busted.
  • Third, I typically travel on my own, book everything as I go and let my intuition guide me at my destination – I did not find this type of travel easy to do in Cuba so we booked through an agency.  This might actually be the only time I have ever booked a vacation through an actual travel agency.
  • Fourth, I was not AS careful as some American travelers, sure a customs agent could ask to see my credit card records or look up a flight record and see exactly where I was.  Since actually being prosecuted for going to Cuba is extremely rare I took the risk of getting a slap on the hand.

I did some research and found several other informative blogs, but every person will have a different experience.  This is mine.

Booking the trip

  1. The first thing I did was apply for Global Entry – Global Entry is a U.S. Customs and Border Protection (CBP) program that allows expedited clearance for pre-approved, low-risk travelers upon arrival in the United States. Members enter the United States through automatic kiosks at select airports. Via cpb.gov
  2. I travel a lot so this would be convenient, but also allow me to enter the U.S. without a pesky customs agent asking me where I was and what I did – I am a terrible liar and I would have incriminated myself immediately.  FYI – this whole process took 5 months, so apply well before heading to Cuba.
  3. Bought a round-trip ticket to Mexico City per usual
  4. Used skyscanner.ca – the Canadian version of SkyScanner to locate flights from Mexico City to Havana.  AeroMéxico and Cubana had the most flights, but I was worried about the Soviet era planes so I opted for the pricier AeroMéxico flights.  RT from Mexico City to Havana was $400 per ticket.
  5. Stefy and I scoured the net for Cuban vacation packages and settled on one Mexican company.  We emailed them, completed the forms, and were promptly denied a trip since I am a U.S. citizen.  They would not book any Americans on their tours to Cuba.
  6. Back to square one.  We found a trip on a Cuban travel agency website with 2 nights in Havana, 3 days in Varadero, a city tour, and all included transfers.  They confirmed they had no issues booking Americans so we signed up!  They sent us each links to pay for our own parts of the trip.  Two of my cards were denied, presumably because I was sending money to Cuba and not all banks have lifted these restrictions.  Finally my trusty American Express went through!

Travel to Mexico-Cuba

  1. Flew to Mexico, stayed one night with my friend exploring Mexico City – a MUST see, I will write another blog on that.
  2. The next morning we went to Benito Juarez airport at 6am, 3.5 hours before our flight.  I thought that was excessive, but we had heard traveling to Cuba can be cumbersome so we just went with it.
  3. Holy heavens, 3.5 hours was barely enough time to check in!  The check-in line at AeroMéxico was over 2 hours.  Once we checked in we had to go buy our Cuban Visas.
  4. On the way to your gate there is an unmarked kiosk where you must purchase a Cuban tourist Visa for cash USD $25.  This is literally a handwritten Visa and it takes about 10 minutes to get it without a line.
  5. To my surprise we did NOT have to do exit customs at the airport, I had read that from other bloggers and other outbound destinations that this is the case.  This would leave you with an entry stamp, an exit stamp, and then another entry stamp which can alert a customs agents to your wanderings.  Phew, one bullet dodged.
  6. With time running out we had time to run to the bathroom, grab a coffee, and then suddenly at the gate as they were boarding THEY WERE CALLING MY NAME!
  7. Crap!  What was going on?  I had done my research, got to Mexico, was checked into my flight to Havana, what did I miss?   This was not blogged about anywhere!  I went up to the desk and they asked me if I was a U.S. citizen and asked to see my passport.  I started to panic, I thought I was going to be denied boarding.  I confirmed my nationality and showed my passport and Cuban Visa, all while sweating profusely.  They proceeded to hand me an official AeroMéxico form that said something along the lines of ‘I am a U.S. citizen traveling on AeroMéxico to the county of Cuba and I ascertain that I have received permission from my government to be visiting Cuba.’ There were several check boxes with types of permissions, none of which I had, so in the heat of the moment I checked something like ‘humanitarian effort for Cuban people’, signed my name, handed it in and walked away.  At this moment Stefy was in the bathroom and she came up to me and said she heard them calling my name, I told her what I just did and she said ‘Dios Mio! I am so glad I didn’t see you do that, I would have been freaking out!’  Quite frankly, she was as nervous as I was breaking U.S. laws.
  8. I was nauseous on the flight to Havana, I was thinking I just lied on a form, I am in so much trouble! Oh well, let’s take a nap and pretend none of that just happened.

Arrival in Cuba

  1. Arrived at Havana International Airport.  Only description: THROWBACK.  That airport is like some relic of the 1950’s.
  2. For this next part I was absolutely terrified.  As if we hadn’t filled out enough forms in Mexico CIty, there were more forms upon arrival.  I was scared to go to the immigration desk alone so Stefy went with me and the agent politely asked us ‘are you both over 18 and adults?’ we said yes, she replied ‘then you have to each do this separately.’ Noooooo my security blanket was gone!  Stefy quickly retorted that my Spanish wasn’t good and I needed help, the lady said too bad so sad in a roundabout way.
  3. I do speak Spanish, but in heightened moments of anxiety my Spanish falters.  I timidly asked ‘por favor no me sella’ which translates into ‘please do not stamp me’. She was super nice, asked me if I or any relatives had recently been to Africa (turns out even Cuba was nervy about Ebola!), then she simply stamped my visa and told me keep it because that was my exit ticket. .
  4. Glad I asked because Stefy got a bright, hot pink Cuban entry stamp.

Travel back to Mexico

  1. The time came to leave so we boarded our bus back to Havana International Airport
  2. Again we arrived 3 hours early and check in took a long time.
  3. We checked in, got our seats and started to head to the gate.
  4. Here we go again, full-blown anxiety, as we did exit customs I once again asked to not get stamped.  The agent hilariously took the stamp and acted as though he was going to give me one of those glaring pink stamps.  I think I blacked out. Then he just lol’d and stamped my visa, kept it, and sent me on my way.
  5. I could’ve done without that mini-heart attack.
  6. Arrival back in Mexico, one of the last hurdles I thought! I needed to persuade the immigration officer to not give me another entry stamp, I already had one from my arrival into Mexico a week ago.  Some might call this bribery, I called it humanity.
  7. I very nicely and politely asked the officer to not stamp me because I had been in Cuba and I could get in trouble for having been there.  He looked at me and said he could get in way more trouble than me by not stamping me so tough luck chica! I quickly improvised and asked if he could just conveniently stamp right over my last entry stamp making both illegible, he pretended to ignore me, did exactly that, and wished me a great stay in Mexico.
  8. Hot damn I was on a roll! All I have to do is get back into the U.S.

Travel back to the U.S.

  1. I spent another night in Mexico City and then went back to Colorado the next day.
  2. Upon arrival to the U.S. I was nervous, it was my first time using Global Entry and I wasn’t sure if I would still need to be checked as like a ‘let’s make sure you are actually a trusted traveler’.  I was screwed if I did get caught, I pathetically hid the 4 cigars and coffee I bought in my bag.
  3. U.S. customs = total breeze.  Walked right through, then nearly ran to my car to drive away… I secretly felt like a criminal running from the scene of the crime.

For those bloggers who write about this trip as ‘easy’ or ‘not difficult’ are not people that I know.  I would, however, like to know where they get their confidence fairy dust because I was fully frightened in each of the steps above.

Happy Travels!

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1Comment
  • Amanda
    Posted at 03:02h, 11 September Reply

    Oh my god I had no idea the headache you had to go through with travel alone! I laughed several times while reading this as I pictured you telling the story out loud, haha. I’m so glad you didn’t get a hot pink Cuba stamp!

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