Back in 2012, my wife Megan was six months pregnant with twin boys. We wanted to take a slightly adventurous “babymoon” with our four-year-old daughter while our family was still a power trio, as the five-piece version seemed like it was going to be resigned to Orlando timeshares with the in-laws for years to come. 

So we flew right on past Florida and took a two-week trip to Cuba. One last hurrah for the three of us before the twin wave arrived with…whatever it was going to bring.

You still have to jump through a few hoops to get to Cuba from the United States. There are permits you can apply for to get there legally for a slew of reasons, but we’re not planners and instead just flew to Cancun and bought three tickets to Havana in cash at the airport.

As the more neurotic partner in my relationship, this leap of faith brought with it a lot of stress. I spent countless hours online researching the worst case scenarios – penalties for being caught, and options for when you run out of cash and your American credit cards won’t work. Was there even an American embassy in Cuba?  

I know six words in Spanish and they are: por favor, no empuje mi pasaporte. I even roll my r’s when I say it.

As it turns out, my wife’s fearless, willfully ignorant, the-universe-will-provide attitude was all we really needed. She told her OBGYN we were hoping to take a trip six months into her pregnancy. When the doctor found out the trip was to Cuba, she said, “Oh, that’s fine, they have great health care.” And we were off. 

babymoon-cuba

Havana

It would have been easy to spend two weeks in Havana alone, jumping from casa to casa. Casas Particulares are homes marked with triangles above their front doors that have government-sanctioned guest rooms for rent. 

The beauty of traveling to Cuba, for me, is staying at the casas, talking to the hosts, learning about the island

When you stay at a casa for about $30 a night, you get a bed, an air conditioner, a blindingly fluorescent light, and a four-course Cuban breakfast made with love before your eyes. A plate of mango and papaya is a great way to start a day. 

The beauty of traveling to Cuba, for me, is staying at the casas, talking to the hosts, learning about the island, and always learning about their friend who has a casa wherever it is you’re going next. The Cuban people are a resourceful team and they help each other out. 

While some people might prefer the privacy and comfort of a proper hotel – and they exist in Havana – to me, much of the reason to make a trip like this is to get to know the locals. Interacting with your host is a perfect way to do this. The internet’s not going to work at that hotel anyway.

The embargo has essentially created a time-warped island where cars are preserved relics from the 50’s, oozing charm and oil. I remember getting into one particular cab that was a perfect Studebaker with checkered red and white leather seats. We were so impressed we immediately told our driver this was our “favorite car yet.”

“Where are you from?” he asked us.

“New York City.”

“What kind of car do you have there?”

“A ’95 Ford Explorer,” I answered.

“Trade you?” he said. 

 It’s good to remember that our little museum is their daily functional struggle.

Havana is broken up into three sections.

Habana Viejo (Old Havana) is where you can gawk at prestigious plazas and streetside mansions. Keep some CUPs (the local currency, not the tourist currency) on hand to pick up pizzas in the street windows. 

Centro Havana, the more bustling and crumbling area in the middle of the city, is where we stumbled upon a restaurant called La Guarida. To reach it you walk up flights of winding stairs, through tenement apartment hallways littered with toys, to a gorgeously renovated room serving upscale food. 

Finally, there is Vedado, where the streets are wider and there’s a more suburban feel. In Vedado we stayed with a wonderful host named Eddie who had a mini outdoor shower draped in vines that our daughter found irresistible. 

Outside Havana

The noise and exhaust of the city eventually caught up with us and we pulled off a pretty rare move – we rented a car in Havana and got out of town. The car rental places aren’t cheap and you must pay up front in cash. It feels super sketchy, and how did a 1982 Toyota Corolla end up here, anyway? The maps are hilariously vague and have nothing to do with the actual roads, but the universe will provide.

There are wonderful destinations throughout the island – beaches, mountains, villages – and the casas are not confined to Havana. It’s best to shop around for a special casa if you can. For an extra $20 you might find yourself eating breakfast on a swanky rooftop or staying in a mansion with an incredible library. The simple pleasures brought us the most joy – like a little pig that ran around the backyard at one casa in Trinidad. 

Outside of the city, the spirit of the Cuban people is easy to experience. As a socialist country, the culture doesn’t compete like Americans do, and there is a more relaxed team spirit that pervades the daily culture. If a car is stuck with a flat tire, the next car along the road pulls over to help. That’s just how it works. 

“Let’s get another!” my daughter would yell every time a hitchhiker got out.

Hitchhiking is a common mode of transport and no one drives past a hitchhiker if they have room (or sometimes if they don’t). Wanting to immerse ourselves in the culture, we started picking up hitchhikers on our route, too. They’d sit in the backseat next to our daughter and would slowly realize they’d been picked up by a bunch of gringo tourists. 

After a little Spanglish conversation about the gemelos Megan was expecting, most would end up playing with our daughter a bit before gesturing to get dropped off. Our daughter loved it. “Let’s get another!” she’d yell every time a hitchhiker got out.

Once, when we pulled into town on the late side – like 9 p.m. – our casa host directed us to the one restaurant there, but it had just closed. Someone from the restaurant then escorted us up a hill to a friend’s modest apartment. The woman answered the door with curlers in her hair but understood the situation. 

We sat at her kitchen table while she prepared us fish, beans, and plantains. She made sure we were satisfied. At the end of the meal she slid us a piece of paper with the number eight on it. We left her ten dollars and a bunch of soap we didn’t need.

As a babymoon, it was the perfect destination to stimulate the three of us.

Everyone in Cuba is hustling a little bit – they need more to live than the government ration provides. It’s good to have your antennae up as some of the people who approach you have ulterior motives and are running low level scams. But much more often we experienced their generosity, humanity, curiosity, and a gratitude that Americans took the time to explore their country. 

As a babymoon, it was the perfect destination to stimulate the three of us. We bonded, had some adventures, learned a lot about a wonderful island, and made some new friends. We left our “Time Out Havana” book on the street in Cuba for someone else to enjoy. When the guy at U.S. Customs asked if we had a good time in Cancun, we said, “Yes… Cancun was sweet.”