Everything You Need to Know about Exploring Havana with a Child

Although Cuba has been a regular travel hotspot for a long time for many Canadians, Havana isn’t usually the main destination but rather a quick day trip from a resort if visited at all. Most Canadians take advantage of the cheap all-inclusive vacation packages sold that include a direct flight from Canada heading straight to a big all-inclusive beach resort somewhere on the island. Even though I’m Canadian I had never been to Cuba and spending a week sitting around at an all-inclusive was definitely not the type of trip we were looking for.

This year my daughter turned 3 & for her birthday we wanted to take her on a little getaway. I’ll be honest that Cancun, the Riviera Maya & the Yucatan Peninsula keep us pretty entertained living like we’re on an endless vacation…but it’s also nice to squeeze a little travelling in whenever possible. I’m kind of obsessed with the idea of watching Isla see the world and getting to experience so many new & fascinating things right along side her. We only went on a short 4 night trip and truthfully we weren’t trying to cram in a million different things or attempt to see the whole island. We just wanted to stay right in Havana and truly experience & take in the city itself that’s full of so much beauty & history. Most of the popular day trips from Havana are to the beach. Since we live in Cancun we get our fill of beautiful beaches and decided to just stay put in the city to enjoy it. We didn’t book any excursions but instead just winged each day with a few ideas I had in mind from earlier research. Overall we found Havana to be very safe, welcoming & family friendly making it a great place to relax and wander around with an energetic toddler.

Photo by: Ivan Botello (professional photographer based in Havana, Cuba)


We took a direct 1 hour flight on Interjet that left Cancun & was in Havana before 10am. We have flown a lot with our daughter but we have become so used to an average of 4 hour flights with her since birth that a 1 hour flight was an absolute piece of cake. It takes us longer to drive to Playa del Carmen from our house in Cancun some days than it did to fly to Cuba. It seemed as if we were ready to make our descent just moments after the seatbelt sign had been turned off from reaching altitude after take-off. I don’t even think I pulled out one item from my mom bag I always prepare to entertain my toddler for air travel. It was such a quick, easy & perfect flight she was content looking out the window & feeling the change in altitude as she’s getting old enough to understand things like that now!


Cuba has been known for operating an Airbnb style of personal home/apartment rentals forever…long before Airbnb was popular. They are called “casa particulares” in Cuba. We did however decide to rent through Airbnb because we felt more comfortable with how easy it is to rent a place through the Airbnb site, the amount of information such as location, apartment details & host information that’s provided through Airbnb ahead of time and the chance to read reviews from past guests. I also felt as if it would be more comfortable to stay in a rental vs. a hotel with a toddler. There have been times when we’ve travelled that it wasn’t a huge deal where we stayed but for our trip to Havana I just knew that where we stayed was going to somehow make or break our trip. Thankfully in our case we found the perfect place to stay which totally made our trip that much more amazing!

We stayed in an Airbnb rental hosted by a designated Superhost. I considered information about the location, overall price & reviews when deciding where we would stay. I also really wanted a room with a balcony or large floor to ceiling windows that opened up to take in the city. In the end I couldn’t have been happier with our choice. We stayed in a small one bedroom apartment in Old Havana just steps from Plaza Vieja. What I loved about the apartment was that the Airbnb host lived in the building so he was always available to help answer any questions, arrange transportation or an excursion for us, exchange money for us, sell us WiFi cards & give us a fun sense of belonging. It was really nice bumping into our host in the mornings and having him ask how we were doing or if we needed anything. Our daughter is always very friendly but she especially liked our host Jorge.

One of the other main selling points to Jorge’s apartment in Plaza Vieja was the rooftop patio. He rents out several apartments in the same building and all guests have access to the patio on the roof overlooking the city. It has a great view to take in Old Havana and you can see right over to the cruise ship terminal. Mornings & evenings around sunset were absolutely breathtaking on the patio. There was also lots of space for my daughter to burn off some energy & play in between outings.

Another bonus with our rental was our host offered a breakfast each morning to all guests on the rooftop patio. Having a bed & breakfast type option or a meal for a small fee is quite common with Cuban rentals in Airbnb homes/apartments or casa particulares. Before we arrived I knew the rooftop breakfast was an option but wasn’t too sure if we’d take them up on it. In the end we ate up there every morning and it was by far the best meal we had each day! They prepared eggs any style you chose with meat, cheese & vegetables, gave you fresh fruit, freshly prepared juice, home baked bread with homemade marmalade. It was really good and very cheap at the equivalent of about $5 U.S. per person.

Getting Around City Streets with a Toddler

We knew we would be doing a lot of walking while in Havana but we hadn’t really figured out if that meant with a stroller or carrier. I have always been a mom that has almost equally bounced between both depending on where we were or what we were doing. Isla being 3 years old means we’re in a bit of a transitional stage where we definitely don’t use the stroller very often anymore but we’re not at a point to completely get rid of it yet for long days out. We did bring both our stroller and carrier to be prepared.

We landed right at the José Martí International Airport in Havana. It’s a fairly small airport and easy to navigate through but not really accessible or stroller friendly. At one spot we had to pass through there was only an escalator as an option to go down and in another area there was an elevator that was broken so we had to carry the stroller down a large flight of stairs. It wasn’t a huge deal since we travelled light with only two small carry-on suitcases for all 3 of us but it took a little extra maneuvering.

Our first day we excitedly covered a lot of ground walking around the city so we took the stroller but quickly learned that the narrow sidewalks didn’t really make Havana stroller friendly. Our stroller is fairly light & small and does great over cobblestones or uneven surfaces but the sidewalks were barely wide enough for me to walk on it let alone with any type of stroller. We also noticed a lot of construction forcing pedestrians to pass certain areas anyway on the road so it was a hassle with a stroller to jump back and forth between the sidewalk and road every other building.

We found it much easier to carry our daughter in a carrier for those stretches her little legs were too tired to walk anymore on her own. I have a Tula Toddler carrier and absolutely swear by it. It’s comfortable for both of us, easy to get her in & out of it and made of super lightweight breathable material (which is of course tested on a regular basis here in hot & humid Cancun). When she’s not in it I can leave it hanging around my waist without it feeling really clunky. Other than the waist support it’s all just made of a lightweight cotton canvas so it’s comfortable to leave hanging or I can roll it up pretty compact & throw in my bag for the same reason without feeling as if I’m lugging around an awkward contraption.


After the first day in Havana we realized we could let down our guard a bit. Exploring a new city can always be a little daunting until you get your bearings and a feel for the people. I think in general a good traveller is always aware of their surroundings and careful but we quickly realized Havana wasn’t one of those cities we needed to be overly cautious. We had a funny exchange with a taxi driver who dropped us off late one evening who laughed at us thinking we were paranoid trying to walk back to our apartment along a route that was quite longer but with more lighting. He basically told us there are no violent crimes in Cuba and we had nothing to worry about. Again it doesn’t mean that’s always 100% true & that you completely stop worrying or thinking about how you travel but we did enjoy the safe feeling we had walking the streets at all hours during the day and evening with our toddler daughter.

Plaza Vieja

We didn’t really have an agenda on this trip with a long list of must see places & must do activities. Instead we just wandered around! Since our Airbnb rental was located in Plaza Vieja we spent a lot of time just hanging out there. There are several great plazas or squares located throughout Old Havana. We did spend time in each of them but spent the most time in Plaza Vieja as it was closest to our rental apartment. We also felt it had the best vibe out of any them. We would walk through the square and grab something to eat or sit down and have a drink. There was almost always live music with a band out front of one of the restaurants so it just made for a really nice atmosphere. Isla also loved dancing every chance she got as well as playing with kids in the square.

Plaza Vieja is strictly pedestrian only so there aren’t any cars to worry about in front of the restaurant or cafe patios. We could conveniently grab a table outside and safely let her play in the immediate area around us without any worries. We loved that the square would fill up not just with other tourists but a lot of local families from the area as well. One of Isla’s favourite times of day was getting to play with all of the kids on their way home from school walking with their parents or grandparents. We watched her play impromptu games of chase, catch the balloon & balance beam walking on small curbs with kids in their school uniforms. She was in heaven in Plaza Vieja and so were we!

Food, Snacks & Drinks

I learned that everything I’ve heard about food in Cuba was true. There definitely isn’t a ton of variety when it comes to food options in restaurants and the food you do find in the busy tourist areas is still a little bland…and expensive! We were actually shocked just how pricey most things were in Havana for not the greatest meal or portion size but with such a fun vibe in the city you just make the best of it.

One of the other things we noticed was there really weren’t many convenience stores. I think we only passed one the whole time in Old Havana and when I ran in looking for chocolate milk or juice they looked at me like I was insane. For that reason alone I did bring at least half a small carry-on suitcase full of snacks with us. With kids it’s always better to be prepared with some of their favourite go to snacks just in case. I brought things like snack bars, cookies, crackers & small snack size cups of peanut butter for all of us to share. I also brought a package of soup & a few small boxes of cereal. My daughter at the time was still quite fussy with the milk she’d drink so I brought powdered milk with us and I’m so glad that I did.

Horse & Carriage Ride

We did a horse & carriage ride through the city on our first day and it was a great way to get aquatinted with where everything was. Old Havana is small enough to walk but it’s nice to get a feel for where everything is or just how far instead of only referring to the map. Our horse & carriage ride went through the city at the perfect pace to take everything in and overall was just really nice and lots of fun. The drivers are also full of tons of information pointing out buildings of significance and the history behind them. Kids also love animals so a horse & carriage ride is always a win win situation.

Vintage Cars

All through Old Havana there are people offering rides in classic cars and tours around the city. We decided not to do a proper tour since we already saw the city by horse & carriage. Instead we just sought out classic cars that also operated as taxis. They cost a bit more than the regular taxis but was a fun way to get to our next destination if we needed a ride. If you’re headed somewhere that you’ll likely need a taxi ride back, most drivers will try and work out a deal so they can take you there and arrange to pick you up again.

Cannon Ceremony at La Cabaña Fort

This was one of the few things I had on my to do list ahead of time. I had read about the cannon ceremony that took place each evening at La Cabaña Fort and knew it would be something we would enjoy. Castillo de San Carlos can be seen from just across the port area of Old Havana. It’s only accessible by car (there’s no option to walk across the bridge) so that was the perfect opportunity for us to flag down a vintage car to get there (cost there & back was about 20 CUC). Young military men dressed in period costumes perform the ceremony that’s based on a tradition that started in the 18th century. The firing of the cannon was to notify the surrounding communities that the gates to the city would be closing. Now every night at 9pm the cannon is fired and visitors are invited to watch.

You can go at anytime during the day to explore the fortress. If you’re planning on just going for the cannon ceremony it’s still worth it to arrive early to take everything in including the panoramic views of Old Havana and to get a good spot near the cannon before the ceremony begins. Our daughter enjoyed the whole ceremony and wasn’t too bothered by the noise but it is pretty loud because it’s meant to be heard all throughout the area. If your little one is nervous around loud noises you can try to place yourselves somewhere you can still see but not too close.

Kids Park

We found a great little park for local kids in Old Havana. I hadn’t read about it beforehand but just sort of stumbled upon it while exploring the city. I say it’s a park for local children because there was a small admission for each child to enter but the pricing was only in Cuban Peso (CUP…the currency for locals). The lady at the gate quietly allowed us to pay in Cuban Convertible Peso (CUC) and waved us through. Entrance probably worked out to the equivalent of less than a dollar 

Inside the park were different outdoor play areas filled with a variety of traditional playgrounds and lots of inflatable jumping castles & slides. Isla had a blast running around to check everything out and had lots of fun jumping with the other children in the bouncy castle.


The whole reason for our trip was for a little getaway for our daughter’s 3rd birthday. I excitedly packed a few birthday decor type items in our suitcase and had one small toy for her to open the morning of her birthday. We’ve technically spent her actual birthday day in a different spot each year between her being born in Canada, turning 1 on the beach in Cancun then turning 2 in the Riviera Maya so it just felt fitting to head somewhere fun as a family for her 3rd birthday.

I had let our Airbnb host know that we would be celebrating our daughter’s birthday while we were there and he blew us away with his thoughtfulness and kindness. Our Airbnb host threw a little birthday party for our daughter on top of the rooftop terrace. He had arranged for some finger foods to be made, got a cake & invited kids he knew from the neighbourhood to attend. It was the absolute best experience and such an amazing memory for us to share with our daughter one day about how awesome her 3rd birthday party was.


Each year for our daughter’s birthday we do a special birthday session of her. This was only her 3rd birthday and we thought having her 3rd birthday photos done in Havana during our vacation would be the perfect way to celebrate. Although we are professional photographers we prefer not to travel with our gear so we can really enjoy ourselves and take everything in without worrying about our equipment. We also wanted to take advantage of the chance to get some family photos done.

We were extremely happy with the professional photographer we found. His name is Ivan Botello. He was born & raised in Havana & speaks perfect English. I had told Ivan I wasn’t after perfectly polished backgrounds but wanted the beauty of real Havana to come through in our photos and that’s exactly what he gave us. We walked the city streets with him stopping at some of his favourite spots along the way and then headed over the the Malecon. Going through the city with him and hearing some of his stories became a bonus personal tour. Ivan’s photos perfectly captured our family and the charm of Havana. They were exactly what I was looking for as a keepsake from our trip & daughter’s birthday!Photo by: Ivan Botello (professional photographer based in Havana, Cuba)

Photo by: Ivan Botello (professional photographer based in Havana, Cuba)

Photo by: Ivan Botello (professional photographer based in Havana, Cuba)

Photo by: Ivan Botello (professional photographer based in Havana, Cuba)


Wherever there is WiFi in Cuba you’re still required to purchase a card from ETECSA. Even WiFi in an Airbnb isn’t “free” and is restricted & controlled by the government. We really only logged in a few times to check emails quick & to share a few photos. I don’t think it would have been worth the money or headache of getting cards and the entire login process each time to continuously try and be online.


We loved just wandering around Havana without a plan. We took our time and allowed our daughter to lead the way. If she noticed artwork, statues or a live band that interested her we were completely open to stop as we went along not needing to rush her off to the next sight. It made for a fun way to truly take in the city with a toddler in a non-stressful way. We find she does quite well taking in sights & sounds since she’s an explorer by nature. Havana is an absolutely great city to explore with young children and we will definitely go back again one day.

Photo by: Ivan Botello (professional photographer based in Havana, Cuba)


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