Cuba – Old Havana Walking Tour


Hanna standing in front of a run down pink and purple building with art deco squares on the window bars. This rundown building is in Old Havana.

When arriving at any new big city, it’s a bit overwhelming. This time, in order to combat the overwhelm, I arranged to go on an Old Havana Walking Tour to better understand the city… guess what?! It worked! Walking around the city with a local guide, I was able to orient myself quickly, find landmarks, and understand the cultural aspects of Havana. Because you see, Havana is not a cold metropolis that empties every night when the workday ends. No, Havana is alive with music, dancing, and people living life in the streets. The Havana Tour Company, who I took the tour with, calls the city a sensory experience, which is an understatement. With so much to look at on every street, I found it worthwhile to have an introductory walking tour of the city.

This post contains affiliate links, which means if you make a purchase through these links, I may receive a small commission at no extra cost to you. The commissions help support Moderately Adventurous stay alive and kicking. Click here to read my full disclosure policy.

Havana Walking Tour

Since we were staying at Casa Ninita on the corner of Cuba and Sol, which is the middle of Old Havana, our guide met us at our accommodations to start the tour. Danny, our guide, introduced himself not only as our walking tour guide but also as the guide that would be with us for the 8-Day Cuba Group tour that we were about to embark on the next day. Before even starting the tour, we have our first cultural investigation – baseball:

There is a small open plaza on Cuba and Sol, where about four kids play baseball. Not needing a full team, one person pitches, one is at bat, one catches, and one plays “outfield”. The funny thing was that the bat was a long straight stick and the ball was a rock covered in tape. Kelly (my travel partner on this trip) jumped in to hit a ball and said how hard it is to hit a tape rock with the stick. I am simultaneously impressed with these kids, nervous for the cars and windows in the plaza, and bummed the kids don’t have a bat and baseball. But at the same time, I see how the Cuban baseball players are so talented if they are growing up using all these other objects. Danny says that kids come here just about every afternoon to hit the “ball”.

We formally started the tour on Plaza Vieja, where Danny informed us of historical happenings, government vs. non-government restaurants, current trends, and etc. We made our way down various streets to different plazas. As we walked, we often interrupted to ask all kinds of questions from what we saw to questions about tourism and larger themes. Ever patient, Danny answered questions and also kept telling us which streets we were on and where we were in relation to other things. This was so helpful when finding things later.

At a Glance:

  • Rating: 3 (out of 4) stars, this was a great orientation tour to Havana (and Cuba)
  • Intensity: Flowy clothes and comfortable sandals
  • Location: Havana, Cuba – meeting at our accommodation
  • Cost: $25 per person
  • Restrooms: Only if you pop into a restaurant
  • Timing: 2.5 – 3 Hours

Highlights:

  • Introduction to the city
  • A local guide explaining things as you see them

The Buildings

You cannot go on a tour of Havana without talking about the rundown buildings. Basically, all new construction stopped during the Cuban revolution in the ’50s. Since then, the buildings of Havana have been in various states of disrepair or repair. This makes for a beautiful juxtaposition of seeing a rundown building next to another building with laundry hanging from the balcony. From a modern rooftop bar or restaurant, you’ll see another building with a tree growing of it. I found it to be beautiful but also hope the people living in these buildings are safe. When walking by a building under repair with scaffolding, Danny mentioned how he hoped to see the building completed, but it had already been at least 5 years.

The Cars

Another thing that Cuba is famous for is classic cars. Every postcard of Havana has a classic car somewhere in the photo. Although we didn’t go out of our way to see the classic cars, they are everywhere and will honk at you if you’re not moving out of the way fast enough. Like the buildings, cars were no longer imported during/after the Cuban revolution. Since Cuba does not manufacture cars, they had to maintain what they had for years. Cuban ingenuity is next level. This is not special to Havana but is everywhere in the country. It is also not special for tourists but is legitimately many family’s personal cars. However, if you have a classic car in the family, someone in the family will often use it as a taxi for additional income.

While in Havana, I highly recommend you take a classic car tour, which I did as part of the 8-day tour with Locally Sourced Cuba. You can read about my experience by scrolling down to “Day 8: Classic Car Tour and Goodbyes” on my Group Tour post.

I also took a classic car taxi to the beach outside of Havana. You can read about that in my “Things to do in Havana” blog post.

Cultural Sights

One of the things that struck me about Havana was how many people were out in the streets at all times. There were relatively few cars for a major city, so people walk down the middle of the street at any time of day, which made for an interesting Old Havana Walking Tour. A couple of examples of this were the fortune teller and the photoshoot.

There is an older woman who brings a table and chairs to the Virgin Maria Cathedral plaza. She wears bright, frilly clothes while smoking a cigar. She tells fortunes and allows people to take photos with her, for a small price. There are other women in bright clothing or men in formal clothing smoking cigars around Havana. Don’t be afraid to take a photo, but have a tip ready for them. This was just like our time in Cusco, Peru, where women dress up in their traditional clothes for photos. We didn’t get our fortune read this time, but think it would be fun if we had more time in Havana.

Not far from the fortune teller, on Obispo street, we ran into a photoshoot happening outside a famous restaurant where Ernest Hemingway would have a drink. The model in the shoot was topless and covering herself while focusing on the camera. She was getting a ton of attention by passerby’s, to the point that her focus was impressive. Although getting a lot of attention, no one tried to touch her or interrupt the shot. She did not look like a foreigner, so I found it fascinating how much creative freedom there is in Havana. Perhaps it is the Caribbean influence, but I found it refreshing that women can dress how they please and not necessarily conservatively.

Sites Seen

During the Havana Walking Tour, we visited and discussed:

  • Kids playing baseball
  • Plaza Vieja
  • Plaza de San Francisco de Asís with art sculpture
  • Castillo de la Real Fuerza
  • La Catedral de la Virgen María de la Concepción Inmaculada de La Habana (An incredible Baroque Church)
  • A fortune teller, complete with a cigar
  • Ernest Hemingway’s old watering hole
  • Kids playing a particular game of dominos while using a board on their laps as a table
  • Countless classic cars

Full Transparency

The Havana Tour company is connected with Locally Sourced Cuba, which is the company I took the group tour. Because I was already going on the group tour with Locally Sourced Cuba, I arranged to go on the Havana walking tour through them. Since I was already partnering with the company for the group tour, they decided to give us a complimentary walking tour. I wanted to talk for a second how that would impact my experience of the Havana Walking Tour. First, at the $25/per person price point, I would have done the tour anyways. But without paying for the tour, I had low expectations about what we were going to see. There was a little mixup of timing/guides, so we did not see the exact things listed on the website.

Online, you’ll see the Havana Walking Tour scheduled for 9:30 am. If you are coming in on a red-eye flight, like us, you might not make it into town by 9:30 am. If this is the case, I recommend reaching out to the Havana Tour Company/Locally Sourced Cuba to see if they could arrange it for you in the afternoon. We found that a leisurely morning, lunch, then going on the tour was a perfect first day in Havana.

Overall Thoughts: Havana Walking Tour

After a couple of flights getting to Cuba, I found the Havana walking tour fantastic for getting some gentle exercise in addition to helping to orient myself in the city just when we got there. It was fun to be out with the people in their daily lives, rather than head directly into a Museum. In addition to the Havana walking tour, I did an 8-day Cuba Tour with many inclusions. You can read about the tour and all of my Cuba posts at the following links:

What were your initial thoughts on Havana, if you’ve been to the city? So many people have traveled to this iconic city, but I am curious about what your first-day impressions were. Let me know in the comments!

Happy Travels,

Hanna

Hanna sanding in front of a rundown old building with different colors of teal paint while on the Old Havana walking tour. The old buildings are beautiful in their own way. Text on the image reads, "Old Havana Walking Tour, Havana Tour Company." Moderately Adventurous Travel
Pin Me!
Hanna wearing a pink top and floral pants is quite small compared to large baroque church in Old Havana. We took this photo on the Old Havana Walking tour. Text on the image reads, " Walking Tour in Old Havana, Explore and learn about Cuba's Capital City." Moderately Adventurous Travel.
Pin Me!
Hanna walking along the stone wall of the Fortress, while on an Old Havana Walking Tour in Cuba. Text on the image reads, "Discover Old Havana, Havana Walking Tour." Moderately Adventurous Travel.
... Or Pin Me!


What are your thoughts?