Home Commentary & Short Stories The Cost Of A (Somewhat) Legal Trip To Cuba

The Cost Of A (Somewhat) Legal Trip To Cuba

by Dewan Gibson

In late 2014, President Obama relaxed restrictions on Americans looking to travel to Cuba. The new rules said, in short, that you should feel free to fly to Cuba if your reason for travel fits one of 12 categories: journalism, education, religious activities, and so on. But if you want to go for a different reason, you would just say you’re going for one of the 12 approved reasons, because the government doesn’t really care enough to check.

However, there are few commercial flights from the United States to Cuba. Charter flights are available, but those are thousands of dollars and sound like something you should take if you’re over 70 or seeking to find yourself after a divorce.

I happen to live in south San Diego, just 10 minutes from Tijuana, Mexico, where you can find any vice imaginable and also daily connecting flights to Havana. My wife and I took a vacation to Cuba in March 2016, for journalism, I guess, although I was tempted to check the “other” box on the travel affidavit and write in, “We’re long overdue for a honeymoon, and a roundtrip ticket to Havana was only $442.”

We caught an Uber from home to the Cross Border Xpress, a recently-opened 400-foot tunnel (of the legal variety) that allows travelers to walk directly into Tijuana International Airport from San Diego. The convenience was well worth the $12 fee. We were through security and customs and had our bags checked in about 15 minutes. Tijuana’s airport was adequate. It looked like any ol’ airport in a small American city, except Tijuana isn’t small. The gates were really crowded, but personal space norms are different in Mexico. People typically don’t mind if you stand in front of them and block their view with your ass while they sit.

Once boarded, we were surprised by the luxuriousness of the Aeromexico plane. It was everything American airliners used to be before colluding to lower standards. Each seat had its own touchscreen monitor with free movies—the very same movies I had paid to download on my Chromebook the night prior. Bonus: Beer, liquor, and snacks were also free.

We arrived in Mexico City two and a half hours later, which, along with Cancun, is the south of the border meeting spot for Americans looking to fly to Cuba. Airline staff in Tijuana had said we would need to recheck our luggage prior to boarding the connecting flight in Havana. Staff in Mexico City said, “They don’t know what they’re talking about,” which was true. Our bags were already being loaded onto the plane to Havana. We did have to buy our visa for Cuba. It was about $18, plus an additional $25 in expenses for a steak and panini dinner and a bag of Jelly Bellys.


After a three-hour layover and another 2.5 hour flight, we got to Havana at 11 p.m. For such a supposedly taboo destination for Americans, entry was relaxed, made more so by the attire of airport security. Some of the men had on tan uniforms but most male staff wore nightclub attire — untucked polo shirts or button downs, fitted jeans, and those hip bowling-type shoes that Steve Madden popularized before going to prison. Women wore tight tan skirts and fishnet stockings. We foreigners were required to take a picture after showing passports, maybe to ensure we were sexy enough for entry. The attendant asked if I had been to Africa in the last 30 days. The question caught me off guard. I actually had to think about my answer. “No.” She then asked if I wanted my passport stamped. I did, and she smiled. My wife, Amber, refused the stamp. She got a disappointed look in return.

We grabbed our bags and walked past a long line of people checking pallets full of goods. Our driver, Ismael, was there holding a sign with my name on it. The owner of the casa particular (private house) we reserved had arranged pickup. The three of us managed a stop-and-go conversation through limited English and Spanish as we waited to exchange currency.

(Note: About that currency exchange…Cuba has two currencies, the Cuban national peso (CUP) and the Cuban convertible peso (CUC). Visitors to Cuba use the latter, because it’s pegged to the U.S. dollar. However, there’s a 10 percent penalty on exchanging American dollars, in addition to a three percent exchange fee. So you’re better off exchanging American dollars for Canadian dollars or euros prior to your arrival, which can be exchanged penalty-free in Cuba. We had $440 set aside for our five-day trip (the Trumps we are not). This $440 netted us 565 Canadian dollars at a currency exchange in San Diego, which we then exchange for 405 Cuban convertible pesos in Havana.)

We arrived at our casa particular around 1 a.m. It ran us $89 a night through Airbnb, which was steep for Havana, but it was right next to the Malecón, Havana’s famous seawall. The apartment was simple and private, separated from a modest home by an in-house wall-to-ceiling gate. The phone was rotary and the furniture decades old. The bed could comfortably fit two people provided that both slept in a fetal position. The water got hot after bit of a wait and the bedside lamp was soft enough for reading.

We unpacked and found a bar at the top of what looked like a tiny castle. The drinking options were limited. An elderly woman and bar-back served the national beer and aged rum as groups of brown, black, and white teens danced and grinded to reggaeton. A Jackson 5 concert played on a box TV. This would have been a cool spot if I didn’t have regrets older than most of the people there. We left and walked alongside the Gulf of Mexico. More teens sat on the seawall, making out and tossing empty beer bottles into the sea. Hunger set in, but there was no food to be found. Even the corner grill advertising food “24 horas” said they had nothing left to serve.


My shower was interrupted by a visitor: the zika man. The island had a single case of the disease so President Raúl Castro sent 9,000 soldiers door-to-door to fumigate for mosquitoes. I can’t imagine this happening at home. We can’t even conduct a census, let alone prevent a potential public health emergency, without actual elected officials claiming it’s part of a plot by our president (who may have been born in Zamunda) to implement slave camps. Anyhow, Private Zika seemed perturbed that my shower and lotion routine had taken him a minute or two off schedule. I said hello as I rushed out the room carrying shoes and socks. My greeting was not returned.

Cab rides in classic cars are fun and all, but Havana’s a great city for a walking vacation. While there’s a chance you’ll be swallowed by crater-sized potholes and suffocated by diesel fumes, walking is the best way to experience the city’s vintage allure. That morning, we started what would end up being a 20-plus mile voyage. Our first stop was a fancy restaurant in Vedado, one of Havana’s more well-to-do neighborhoods. By “fancy” I mean the plates were anywhere from 5 to 10 CUCs, with, again, one CUC equaling one U.S. dollar. We filled our stomachs with ceviche, octopus, and sausage skewers. It looked like something from an Anthony Bourdain show. I could almost see him there enjoying it, a toothy dark-yellow grin across his face as he cracks an off-color joke.

We continued on to Centro Havana, rudely looking through the open doors and windows of tiny shacks filled to capacity with generations of families. It seemed most people had something, but many had very little. The standard of living would be considered second world, but there were far fewer street beggars and homeless than you’d see in any major American city. The people we met in passing were surprised when our accents gave us away and happy to have us there. Many had an American connection and story—a son, brother, or ex-wife who was living in the United States.

The hours and miles piled up as we made our way through the shops and sites of Old Havana and various side streets that all seemed to blend together. Excitement and curiosity kept us strong as we dehydrated ourselves with spirits from tiny bars. We bought art, an original painting featuring the bright hues of Havana’s homes for 20 CUCs, and of course more food, including dinner at a more typical, less touristy Cuban restaurant for just 18 CUCs. We had been in the streets for over 10 hours. We went back to our casa for a nap to prepare for a long night of bar hopping. The nap lasted until morning.


My right thumb healed. It was tender and burned from years of obsessive scrolling on a heated smartphone screen. There’s absolutely no internet or phone service in Cuba for customers of American service providers. Even for Cubans, wifi is very limited and people are forced to interact with their heads up. We were able to make one phone call in Havana. It was from a landline in a hotel lobby, manually connected by an operator who sat within earshot of the phone booth. The cost of a three-minute call to see how crazy our toddlers had driven Grandma and Grandpa: $12.45.

The highlight of our day was a free outdoor concert by Major Lazer, the first show by a major American artist here in over 50 years. Thousands packed into a square half the size of a football field. More stood atop the seawall, bobbing to the music and waving the national flag. However, there was a conspicuous lack of twerking and marijuana. (I later learned anti-marijuana laws in Cuba are very strict. Users can face two years in jail. Twerking is legal but evidently not widely practiced.) I also didn’t witness a single fight. People didn’t mind if you accidentally stepped on their shoes, though they weren’t wearing Jordans. It was as if no one wanted to be that person who ruined the big event. I found that refreshing and much different from home, where some people actually go to a concert just to mess it up for everyone else.

After the concert and miles and miles of walking, we stumbled upon an outdoor restaurant. Two locals loitering nearby took it upon themselves to join our table. They asked about American football and our lives back home. I enjoyed the conversation about as much as one can enjoy having two grown-ass strange men seat themselves at your dinner table while out with your wife. I asked them to leave, and they politely agreed. They came back maybe 20 minutes later and asked if we had anything to give from the U.S. I had nothing besides an unopened Hot Wheels car. I felt bad, having just engaged in typical American excess by ordering two meals for myself after being unable to decide on a dish (total cost was just $7). He gladly took the Hot Wheels. We left the table an hour later and one of the guys popped up again, asking if we had plans for the night. I yelled “home!” and strongly walked away.

We were actually going to a nightclub. Unfortunately, my stomach wasn’t going for it. I’m unsure whether it was the ice cubes or the two dinners, but I needed to make an urgent drop-off at the nearest restroom, which happened to be in an emergency room. It turned out to be a typical public bathroom in Havana: a filthy toilet without a seat, no running water, and not a lick of tissue. My first thought is to call for Amber, as she’s supposed to be there for me through sickness and health. But she’s in the waiting room and we don’t have working cell phones. Plus, the rush has already started. Damn. My squat was too high and I splashed the back of my pants. I removed my socks, special pink and purple ones that my son picked out for Christmas, and used them as tissue before tossing them in the trash. I stormed out the bathroom and into the waiting room, embarrassed and soiled. I yelled like DMX, or Teddy Pendergrass when he’d tell his woman to turn off the lights: “Amber! Let’s go!”


We awakened to a blackout. Havana is a hard working city. People are constantly in motion fixing cars or patching infrastructure, but the loss of power put most at a standstill with little to do but sit on the sidewalks and chat and stare at my wife. We walked over a bridge and through Miramar, Havana’s upscale beach community full of colorful large homes and foreign embassies, and found a restaurant near the water that had power. The view made up for the two-spoonfuls-and-done seafood soup and flying table umbrella.

After a nap, we went to buy cigars. I’m more partial to the occasional puff of reefer and know very little about cigars, but of course all my hyper-masculine friends asked that I bring some home. Apparently, legit Cuban cigars are marked with a hologram and only available in state stores. The costs vary from a couple-few dollars each to “Damn, I better not even touch that box.” I settled on a $15 box of three Habanos. Americans can bring back up to $100 of Cuban cigars and rum and $400 of other goods. However, U.S. custom agents may or may not be familiar with those rules.

Later that evening, we passed the scene of The Emergency and went into the nightclub we had failed to make it into the previous night. It lacked the character of Havana’s side street dive bars, but made for great people watching. The men had their hair styled more than the women. Designs were shaved into the sides, while the hair on top was teased and flipped. They danced in groups, surrounded by decor that looked as if it was designed by Tubbs and Crockett. There was no DJ, but a DVD and sound system played reggaeton. It was actually the same DVD we had seen in airport driver’s car. After a martini for Amber and a double shot of aged rum for me, we called it a night.

We got less than four hours of restless sleep. There was an early morning fuel delivery to the gas station adjacent to our casa particular and it filled our room with fumes. We tidied up the place and spent our last moments in Havana shopping for small gifts — candy and more cigars. Our driver and his friend arrived to take us to the airport. They talked amongst each other as we shot video from the backseat of the car, getting a passing glance at areas we had overlooked. I felt a bit of regret for not staying longer, but I also felt lucky to have made the trip before the arrival of McDonald’s and Walmart. We reached the airport and exchanged our last bit of currency for 30 Canadian dollars.

After arriving in Tijuana, we walked through the Cross Border Xpress and waited to cross through U.S. Customs. I claimed the Cuban cigars; the agent said I couldn’t bring anything back from Cuba unless I had a direct flight from Havana. I explained President Obama said something entirely different. The agent replied, “That’s good enough for me.”

Amber was not as lucky. The agent she saw, a beefy guy with a heavy Russian accent, demanded she go into secondary inspection for questioning about a single cigar. (I forgot to keep all the questionable items in my bag and therefore failed as a husband and mule.) She was asked to empty her bag completely. “I have to clear this with my supervisor,” the agent said. I was told to leave the area. Twenty minutes pass and Amber came out unscathed. We walked back into the United States. My phone vibrated endlessly with hundreds of text messages and emails, almost all of them completely unimportant, but I still had trouble pulling myself away. We were home.

(Update: Donald Trump rolled back President Obama’s Cuba legislation. Yes, Americans can still travel to Cuba, though it’s supposed to be with highly regulated tour groups. Airbnb is still available, but financial transactions with state-run businesses are banned. As of June 2017, there is no date as to when the new regulations take place, and there likely will not be for many months. So go soon! Or if you go later traveling through Canada and Mexico would be an option. You may also consider voting Trump’s ass out of office in 2020.) 

A Cost Breakdown Our Vacation To Cuba
Two plane tickets: $884.32
Casa particular via Airbnb (four nights): $358.00
Uber rides (had $25.74 in Uber credits) : $5.01
Cross Border Xpress passes: $48
Visas for Cuba: $34.96
Airport Food & Snacks: $25.72
Cabs in Havana: $70
Food in Havana: $163
Snacks & Drinks in Havana: $52.80
Phone Call: $12.45
Gifts & Souvenirs: $49.25
TOTAL: $1,703.96

Originally published in The Billfold

You may also like

1 comment

Traveling Was Too Expensive, Until Google Flights Came Into My Life - DewanGibson.Com February 12, 2017 - 9:23 pm

[…] the birth of our first boy, we are able to travel. Cheaply. In the past year, we’ve flown to Havana, Cuba ($400 per ticket), Reykjavik, Iceland ($300), Columbus, Ohio ($75), Denver, Colorado ($50), and […]


Leave a Comment