Traveling to Cuba as an American — How To, Sanctions, and a Look Ahead

I landed at JFK airport yesterday morning around 730am after a pretty brutal red eye back from Mexico City. Emergency exit row and a window?! Fuck yeah. Seat doesn’t recline and animated older Mexican woman in middle seat reading all night?! Hm. Called it a wash.

After a few minutes of scribbling the familiar passport details on the US Customs form, I started to get a little nervous about getting back in. I had a semi-legit reason to be down in Cuba (I own a small travel company) and was looking to plan trips there for groups in the coming years. Should be good, right? I didn’t exactly have a day to day itinerary with me though and my iPhone was filled with ridiculous pictures of me riding horses on the beach, my friend dancing with an Argentinian girl, and us throwing a baseball around.

I started getting a little more nervous as I got closer to the initial questioning — I almost always get sent into the next room when I come back to the states — my passport and whatever that system is tells a story of 42 countries since 2010, most being in strange ‘high risk’ areas of the world. This was undoubtedly heading in the same direction as I nervously walked up to the counter.

Homeland Security: “Hello. Where are you coming from?”
Me: “Um, Mexico. Well, I mean, Cuba. But flying from Mexico.”
Homeland Security: “Ok…What were you doing in Cuba?”
Me: “Uh, well, I was planning trips. Actually, that’s not a good way to describe it. Let me start over — I’m a travel agent, that uh, plans trips.”

Oh fuck, you really did it this time, Murph.

I sat there with a dumb look on my face, wearing an earthy looking tribal shirt and 6 bracelets, holding my Aether backpack like I was a Swede on a gap year before heading off to university. I started really regretting not having a bunch of documents with me describing the places I went to and what I did for a living.
Homeland Security: “Have you been to Africa in the last 30 days?”
Wait, what? I was confused.
What kind of random question is that?! Don’t you want to know about why I was in a country I’m not really supposed to be in? Don’t you want to know if I have newfound communist views? If I’m stashing cigars in my bag? Or if I’m trying to get my new homies into Miami next month?!
Me: No. Just Cuba… and uh, Mexico I guess.
Homeland Security: “Ok. Welcome home.”

Alright, back up. Why isn’t it chill to just go to Cuba? Are they bad people? I remember hearing about the missile stuff from my grandma but wasn’t that like 70 years ago?!

From my travel experience and some boring days working in Risk at JPMorgan, I knew a little about US sanctions and our relationships with some notorious bad guys of the all-powerful US — here’s my quick, dumbed-down recap on who we have sanctions with to give you a quick perspective on the names Cuba is associated with:

- Burma — Ruled by the military that has done some inhumane things. US prohibits investment into Burma, US can’t import stuff from here, and we can’t export financial services there. Some say these sanctions have been a complete failure — and I would agree. I was over in Burma earlier this year and their banking system is a fucking mess. Here’s a funny picture of a group of bankers trying to figure out how to use a credit card machine to charge me for my arrangements there.

- Ivory Coast –Ugly civil war in 2010 with human rights violations. Since then, we can’t trade with people or organizations that provide arms or assistance to ‘Cote d’Ivoire’. Bush put in the sanctions in ’06 and Obama has continued to renew them, citing an ‘extraordinary threat to the national security and foreign policy of the United States’. Yikes.

- Iran — President Obama’s most controversial frenemy — Harsh US (and allies) sanctions in 2012 have crippled their economy that is driven by their ability to export oil to the outside world. In 2015, the JPCOA was signed, with Iran agreeing to chill out on the nuclear weapons program in exchange for some loosening of the sanctions. GOP not thrilled.

- North Korea — Just straight enemy on this one. The US entered the Korean War to support the South in the 50’s, countering USSR support for North/South to come together and form a mega communist Korea. Since then, North Korea has worked to develop nuclear weapons, commit some pretty awful human rights violations, and only hang out with Dennis Rodman. The whole thing is pretty weird. Obama formalized even more sanctions on North Korea as of yesterday after they launched their 4th successful nuclear test last month. Trouble brewing.

- Syria — Historically part of what Bush called the ‘axis of evil’ (is Bush part of that, too?!). The 2011 Arab Spring turns President Assad against his people (allegedly with chemical weapons), starting a vicious civil war and a refugee crisis. ISIS moves into town, now officially making Syria a failed state. Add in here the Russia support of Assad (US vs Russia proxy war?) and you can officially count on Vice having specials here for the foreseeable future. Avoiding Syria for spring break this year.

- And…. Cuba — The infamous Fidel Castro became Prime Minister, ousting a post-revolution Cuban government in the late 50’s. However, Eisenhower and the US felt as though they were impeding democracy so we said ‘no mas, Cuba’ and put in trade embargoes in 1960. Things got even worse in ’62 with the Cuban Missle Crisis (red angry face emoji at Russia). Since then, there have slowly been a loosening of the rules, with exceptions for humanitarian work and family visits put in place by Clinton and Obama. Most recently, a strangely written 12 reasons are in effect as to if you’re allowed to travel there. More on that below.

Okay so there’s some pretty bad names on there — Iran, Syria, North Korea, etc — Cuba being associated with them on our bad guy lists. This might change soon though — Pope Frank was in Cuba while we were there. President Obama is now heading there next month. The western world seems to be opening up to hanging with Cuba again.

7 things to know about going to Cuba as an American tourist

You may be thinking — So with all that being said, is it cool to go to Cuba as an American tourist? Walk me through this. Tell me some stuff that makes me comfortable with this decision because going to Cuba sounds epic!

  1. Route to Cuba

For Americans, the choice is either Canada or Mexico. Later this year, it sounds like you can go direct from the US with JetBlue. If you’re trying to go for pseudo-tourism, maybe stick to Mexico/Canada though.

I can’t speak to the ease of flying through Canada other than what I saw when I arrived in Cuba. In a week down there, I met exactly 0 other Americans. My friend claims he met a couple, but I never did. Canadians? Hundreds. Direct flights for dirt cheap, all-inclusive deals, etc. It is an alternative to Cancun for them.

Mexico: my choice. I went via Mexico City, and my friends both went from Cancun with similar experiences. Checking in at JFK there were no questions at the gate. Checking back in at the Mexico City airport there were no questions.

2. The Big 12:

As of January 2015, there are 12 somewhat random reasons you can go to the country.

  • Visiting Family
  • Humanitarian projects
  • Official business of the US govt
  • Journalistic activities — Does my new Instagram travel account suffice??
  • Professional research —This was my self-authorized OK
  • People to people travel
  • Religious activities
  • Public performance, clinics, workshops, athletic or other competitions
  • Authorization to provide travel services, carrier services and remittance forwarding services
  • Activities of private foundations or educational institutes
  • Exportation of certain Internet-based services — Hm….

These all sound pretty vague, right? The strange part to me was that no one even asked me which one I was going there for. I filled out a short form in Mexico City at my gate, didn’t even select one of these 12, signed it, and boarded the plane with no discussion. I wasn’t expecting the Mexicans to care, but just seemed a little odd. This CNN article talks about signing an affidavit from your travel provider ahead of time. I’m a travel provider myself and this seems just as crazy as the 12 vague reasons. First, I never had to do that. Second, I am a travel provider but would have no idea what religious activities or exportation of internet services are considered to be cool with the US government. Moving on.

3. Getting the ‘Tourist Visa’

This was the part I was a little nervous about. For some reason, the forums online were a little quiet on this topic other than “you can buy one in the airport”. It is also somewhat ironic that even though you have to be rocking one of those 12 reasons I listed above to get in (none of them being tourism), this card you need is called a tourist card.

I land in Mexico City and go through the rechecking process with Aeromexico. I asked the check-in lady about the tourist visa and she says ‘you grab it at the gate’ and waves in an Asian family with a couple mega roller bags.

After security, I go to the gate and ask for this mystery document again. They direct me to the ‘information desk’, which was right across from a Subway and downstairs from the Centurion Lounge. A young Mexican guy is at the desk playing Candy Crush on his Samsung and looks up.

Me: “I’m an American, looking for a Cuban tourist visa. Do you know where I can find one?”
Information Desk Guy: “600 pesos, por favor.”

He hands me a small green piece of paper.

No further questions.

Tourist Visa Card

4. Accommodations:

Awesome people! We stayed with this family for the night in Jibacoa

You’ll almost for sure be flying into Havana or Veradero, where there are tons of hotels. However, the more authentic way for travel lovers is to post up at ‘casa particulars’, which are basically Airbnb’s and have a logo outside the house that usually looks like the one just below this paragraph. The family is always still there and simply lending you their extra room for 20–25 bucks. They typically made us dinner or took us out on top of that, arranged things for us as needed, etc. We stayed in a different place every night and this really made the trip special — some of the most helpful, patient people, with no judgments about us going out and drinking $3 bottles of rum and coming back to their house. They never tried to nickel and dime us for an extra few bucks and came off as nothing but genuine. Highly recommend staying at these if you make the trip.

Logo to look for a casa particular — cabs know where to find them if you can’t figure it out

5. Currency

A little confusing when you first arrive — there are 2 currencies: CUC and CUP. The locals use CUP ( Cubano pesos) primarily, but the foreigners almost exclusively use CUC. You can get a little more value from the local pesos, but the currency exchanges don’t like giving it to you. My recommendation: Don’t worry about the CUP, just get the CUC (1 to 1 USD) and roll with it. Everything is super cheap anyways.

CUP = locals, CUC = tourists

6. Getting Around

You’ve probably seen the pictures of the 1953 Buicks and old school Fords in Havana, something that reminds me of the once-per-year ‘Cruising Down Woodward’ in Detroit. Cars known as absolute classics in the states are the everyday taxis down there, held together pretty remarkably. Seats in good conditions, with that soft, rounded cushion feel to it and a slight recline in the back. Clutch for passing out on longer stretches.

Taxi drivers in Cuba are some of the richest in the country. Backwards, right?! Here’s why.

Outside of it being pretty epic to be rolling around in a super old-school car, the drivers are absolutely awesome dudes. We were typically hiring them to get us from one city to the next, or to help us find a ‘casa particular’ to stay in. The consistent thing was this: one price, as much time as you need. On one occasion, a driver stopped at some natural caves to let us swim for about 45 minutes. After that, we got to the city we were going to stay in (Mantanzas) and then decided we didn’t want to stay there. No problem! He just kept going and drove us to the next city. On our way back to Havana on the last day, our driver stopped about 5 times to let us do anything from go for a walk, exchange currency, look for some wifi, or get lunch. No issue.

7. Health Concerns:

I got sick as F for about 36 hours. Why? No clue, as with most travel sickness, but had a good stretch of my body saying, “everything is coming out one way or another” Tons of fun.

With that said, I wouldn’t say you need to eat super conservatively. We were staying with families that probably washed food with the water, etc so you’re definitely in danger. I would just take some precautionary meds and be mentally prepared to not feel 100%. 2 of 3 in our group got sick, but no one so bad that we had to get medical attention or reroute the trip. The typical food is a mix of meats (beef and ham mainly), rice, beans, fruits, and a lot of lightly fried stuff with cheese in it. I wouldn’t put it on the top of my international food rankings, but not bad.

8. Other Random Stuff:

- Internet: There is extremely limited access in Cuba. Apparently Verizon and Spring have some plans you can get, but AT&T did not. You have to buy wifi from hotels or dudes on the street and they don’t always even work then.

- Language: Very little English. If you don’t know any Spanish you’re going to be in trouble. One of the guys I was with was fluent so it made the whole thing much more manageable.

- Going Out: Great clubs with salsa dancing. 5 or 10 CUC cover for the best spots with live bands.

- Tipping: Didn’t seem to be a thing, maybe leave the change.

- Talking politics: Wouldn’t run up to people and start asking what they think of the government. But after a little while people seem totally open to giving you their opinion on what’s going on there. Everyone pays 80–90% tax and generally seemed to want to leave.

- Cubans leaving for Florida: One guy told us the way they do it — leave from a little east of Havana (90 miles to Florida) as soon as it gets dark. They row all night until morning. At dawn they put a blue tarp over the boat and stay under it for the entire day just floating. Once night comes, they take the tarp off and row the rest of the way. The cost? $5000 USD, with $500 being deposit and $4500 usually paid by the family when they arrive in Florida.

Conclusion: Can I pull this off or what?!

So should you drop everything and go to Cuba? Not arguing either way on that one. It seems like things are loosening up in a hurry with President Barry’s trip next month and US airlines announcing direct routes starting later this year. If you wait another year or two, most of the above will be obsolete. Canadians are there in full force, overweight older guys rolling around with Maple Leafs shirts and crushing mojitos like Americans do in Mexico. No difference. This is almost exclusively in the couple of resort towns though and Havana.

The advantage of going now is the mysterious factor. There aren’t any Americans there. We haven’t gotten in there to do what Americans do — be obnoxious, force too many of our views on the people, spend a lot of dough, etc. When Cubans asked where we were from, they were expecting to hear Canadian. When we said, ‘American’, their face lit up with curiosity and follow ups. That’s a cool feeling.

What will the impact be of Americans flooding into Cuba as things loosen up? I sure hope it doesn’t turn into the next Cancun 2005. My best guess is that it will for the next few years be a hot bed for travelers — sort of like an Iceland of 2015, with easy access, yet still some mystery around it. As Americans become familiar and comfortable, more and more families will start venturing down and join our brothers from the north with pina coladas in hand.

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