Exploring the streets of Havana (with kids)
Originally published December 6, 2018. Updated March 13, 2025.
On our family trip to Cuba, we saved Havana for last. We wanted to devote ample time to walking around the city, so we decided on three days. For a few reasons, we also didn’t have much of a set itinerary: Mike and I wanted to regain a sense of spontaneity we missed from our earlier (pre-children) vacations, and we also just didn’t have much time to plan before we left. Luckily, winging it worked out pretty well!
Classic cars: yes, they’re everywhere
Our 5-year-old was looking forward to seeing the classic cars, and they did not disappoint. I’d wondered before we left if the photos I’d seen had been strategically shot to only capture classic cars, and while it’s true that there are some newer cars around the city, the classic cars are a prominent element of the landscape (and worth taking a ride in if you can).
Vibrant streets
Opportunities to take dance classes or hear live music abound in Havana. Many of them are at night, however, which isn’t necessarily easy if you’re traveling with children, unless you’re lucky enough to have someone along to watch them—we’d tried and failed to bribe my mom to join us. But we ended up with our very own private music lesson when a kind and talented trumpet player beckoned our son over to try out the trumpet valves after we’d given him a tip to put in the musician’s instrument case. It was one of our favorite moments of the trip, and our son is still talking about how he played his first instrument in Cuba.
A talented Cuban trumpet player shows our son how to press the valves.
We all enjoyed the architecture as well. The usual color palette where we live in New England is generally pretty muted, so it was fun seeing all the colorfully painted buildings next to each other. Some are in rough shape, but we learned that some money from tourism is going into restoring old buildings and keeping the character of the neighborhoods through social programs like childcare, schools, and assisted living to help families stay. It will be interesting to see how that policy progresses and if it does achieve the intended goals.
View from our AirBnB in one of the less redeveloped parts of town. An incredibly sweet couple hosted us. Photo: Emily Dahl
A different kind of architecture: the fortress guarding Havana. This was another of our son’s favorite excursions, but was a relatively expensive taxi ride to and from the main part of the city…it might have just seemed expensive since we were almost out of the cash we’d brought with us. Photo: Emily Dahl
We did book one activity through AirBnB before we arrived: a tour of the city with a university film student as a combined sightseeing/family photography activity. I’ve found that I’m rarely in our vacation photos unless I use the camera’s timer or take bad phone selfies, and for this trip, I wanted to try to get some photos of the four of us together. Manuel is fantastic, and we’d highly recommend an outing with him. He showed us parts of the city we might not have otherwise seen, and other parts that we’d been to but saw with new eyes thanks to his descriptions. The tour includes a classic car ride with him and his taxi driver friend; they were both great with our kids.
Photo: Manuel Casado - Cuban Soul in Pictures tour
One neat thing about Havana we hadn’t known is that the airport is easy to get to from downtown, so with a late afternoon flight, we were able to have extra time for activities the morning we left.
First, we tried the National Museum of Fine Arts has an incredible collection…that we did not get to see much of, as our son had quite a meltdown and we had to leave soon after entering. From what we did see, though, this museum is well worth a visit. I especially loved some of the Cuban landscape paintings.
After recovering from that episode, we stopped in at the National Ballet School—in the morning at breakfast, I’d seen beautiful photos of the ballet school on display in Café el Dandy (great breakfast spot in Plaza del Cristo) and wondered if we could visit. A kind employee showed us around, while his son and our 5-year-old ran shrieking through the echoing halls. Even a brief look at the students practicing showed us why this school has a reputation for excellence.
The building is undergoing restoration now, and it should look incredible when it’s restored to its former glory.
For our flight home, we were on JetBlue’s inaugural direct flight from Havana to Boston, and the crew made it really special. After we booked our trip, we realized we’d be on one of the first direct flights, but it wasn’t until we were at the Havana airport that we realized it was the first. At just over three hours to Boston, it felt as easy as a flight to Florida [2025 note: sadly, this direct flight is no longer available].
With continuing expansion of flight routes and cruise ship stops, Havana and all of Cuba seems poised to experience a huge tourism boom. Already, it’s a lot different from what my friends who visited years ago experienced: the ability to book lodgings and other activities online is relatively new, for example. That means it’s on all of us travelers to help support the Cuban people without compromising the elements that make the country unique, including the environmental and sustainable agriculture heritage we found in Las Terrazas and Viñales. [2025 note: as mentioned in the previous article, the anticipated tourism boom hasn’t come to pass for a variety of reasons; if you’re planning to visit, please look up the latest State Department status update and other news to aid your decision-making.]
I hope we have the opportunity to return—we saw such a small fraction of the island, and would love to get to know it better.