A busy street in Havana

An Airbnb Experience in the streets of Havana

I recently returned from a week-long resort vacation in Cuba — no surprise to my followers, seeing as how photos of Havana are the only images I’ve posted to Instagram in MONTHS. (I truly miss travelling, you guys. But right now it’s just not in the cards until my mother is better. 2018 is not what it promised.)

I really wanted to go to Cuba because 1) It’s a fascinating place 2) I hadn’t been before 3) I really wanted to check out Havana. A good all-inclusive vacation was exactly the tonic I needed after these long winter months in the hospital with mom, but those sorts of vacations are limiting. I didn’t want to see Havana on one of those horrible packaged day trips where you’re herded like cattle to various spots under the guise that you’re there to learn about the history of a place but in reality you’re just there for people to take your money.


Me and my friends stayed in Varadaro, which exists on a different plane. So figuring out how to do a local tour in Havana was challenging. You can Google all you like. Arranging a private taxi to get from our resort (Iberostar Bella Vista) to Havana (a two-hour drive) was a pain in the ass, because no one could understand why we wanted to be there independently. We eventually hired two guys to take us for 180 CUC (about 230 CAD, divided between a group of us), but they could not figure out why we didn’t want to participate in their tour. They were downright insulted. We could have opted for public transportation, but the bus didn’t run early enough for us. So yeah. 360 CAD later…

I use Airbnb a lot, as both a host and a guest. So I was excited to try one of their Experiences. Surprisingly, Cuba has tons of them. Me and the girls decided on a Walking tour with an Economist, because how can you go wrong with a tour that has 141 5-star reviews? The guide, Jorge, seemed like an awesome guy. From his profile: “I love reading about economics and politics, and listening to Cuban musicians like Carlos Varela, Silvio Rodriquez and Pablo Milanés, among others.”

We were a little late meeting Jorge, because our two drivers decided to bring us to lunch at an overpriced restaurant first. (Exactly the thing I wasn’t going for.) And also because I quoted the wrong time. Oops. There were just four other people on the tour besides my group of four, and one of them was Jorge’s beautiful sister-in-law — who, turns out, is quite a popular actress.

Jorge was wonderfully personable and friendly, sporting a t-shirt that said, “Keep Calm and Graduate.” He’s young, and an Economics graduate. We set out on foot in the scorching heat.

Jorge’s tour was all about experiencing Havana like a local, so although I missed the typical museums and monuments, I found myself trailing behind Jorge through the winding streets of Havana, taking in those little vignettes of life — a tiny ginger kitten in a doorway, a vendor selling fruit, a cluster of old men speculating whether or not we were American. Havana is a photographer’s dream. Its brightly-painted buildings with their crumbling facades made for some of the most stunning backdrops I’ve ever seen. The vintage cars just enhanced the experience.

All the while, Jorge told us about his life in Cuba, including how he ended up as an Economics student and how most Cubans have a “side gig” to keep them going. In Cuba, even if you hold a great job in government, you’ll still get paid very little (something like $30 USD a month, according to Jorge). That’s why for most people it’s impossible to survive off one salary, and so they resort to side gigs. When it comes to education, students get very little say in which fields they end up studying — you make note of your top choices, but it ultimately comes down to the institution and how many spots they have to fill. Fortunately for Jorge, he ended up studying one of his passions.

I should note that I was feeling absolutely horrendous by this point. It was late into our trip, and I had been suffering from a case of Castro’s gastro. Coupled with the heat, I was practically dead on my feet. I did not feel good. I hardly took any photos, and was guzzling water like an elephant. I desperately wanted to appreciate every moment of my brief time in Havana, but I was miserable. I definitely was not Jorge’s ideal guest. My relief came when we went to visit Jorge’s grandmother-in-law in her tiny apartment.

Jorge’s grandmother-in-law was sweet and welcoming. She has many side gigs:  she hosts Jorge’s Airbnb guests in her home, she’s a seamstress, and she bakes cakes. She talked about her life growing up in Cuba while Jorge translated to us — she told us all about how the government forced her to leave her family home so they could turn it into a museum, and how she waited in limbo for years for her new apartment where she currently lives. She’s the doting grandmother you’d expect in any culture: her house is filled with ceramic knick-knacks, and her walls are covered with photos of her children and grandchildren. There are cracks in the ceiling and you need to flush the toilet with a bucket full of water filled from the tub, but her home is beautiful.

Jorge and his grandmother treated us like family. We were served insanely large glasses of rum, as well as sugary but strong coffee. I sat on a seat next to the open balcony doors, looking out onto the busy streets below, enjoying the breeze. Jorge’s grandmother brought us crackers and a traditional dip she had made — a light, creamy spread. I felt myself coming back to life after all that. When we left, Jorge’s grandmother stood at her balcony waving good-bye.

The tour lasted about 3.5 hours and cost only $54 CAD each, including some fruit juice and snacks. The whole Airbnb Experience thing is such a wonderful way to dive into a local culture when you have limited time in a place, I’ll definitely do it again. Have you tried one?

  • April 29 2018

    We never take packaged tours and always go on our own and have fun and interesting experiences like yours (but sorry you were not well!). Once in Italy we ended up spending time with an Italian family, invited to a big family dinner, getting a free tour, were offered their car to go see the sights on our own. When we left we were given a bottle of frozen home-made limoncello which I put in my hand luggage back to Armenia (where we lived at the time). While in the air it had popped its cork and you can image the mess in my bag! (Of course I could never have taken this back into the US ;) Yes, we’ve had good experiences with Airbnb and love traveling on our own.

    • May 14 2018

      I LOVE when that happens! All my favourite travel experiences happen with locals. Sometimes you just luck into some amazing hosts.

  • May 09 2018

    Wow! You are so brave. I don’t think I could stay in an Airbnb in Cuba. You hear so many horror stories in the United States regarding Airbnb.
    Alyssa Heberlig recently posted…Ultimate Machu Picchu Resource Guide

    • May 14 2018

      Really? I use Airbnb all the time! I love it.

      • January 19 2019

        I stayed in an AirBNB the first time I went to Cuba, it’s totally fine. Although if you can swing the Spanish it is quite common for Cubans to rent either a room or an entire apartment and its cheaper than AirBNB.
        Ayngelina recently posted…The 10 Most Common Cuban Currency Questions Answered

  • May 10 2018

    I love that his grandma has many side gigs! Cuba is a fascinating country (I plan to go soon), from all the posts that I’ve read it seems that the people are fighters. I didn’t know that usually the students can’t choose what they study at university…

    • May 14 2018

      They’re amazing people! I guess they can choose, but they have to list several things they’d be interested in studying, and then they’re placed accordingly. It’s very interesting

  • May 30 2018

    Cuba seems so fascinating. Your post is making me want to go!

    • May 30 2018

      It’s the best!

  • August 09 2018

    I really want to visit Cuba for exactly the same reasons as you! But I go back and forth about guided tours and I think I settled on that I like them when they’re given by locals and if they are less than 3-4 hours so the one you went on through AirBnb Experiences sounds great. Thanks for sharing your experience with us here. I especially liked your honesty around how you were feeling. My husband and I recently did a long road trip across Croatia and I felt under the weather and exhausted at times so it was hard to be upbeat sometimes. Honesty is always refreshing, so thanks for giving us the real deets! :)
    Kristina Pepelko recently posted…The Good & the Bad of Our Croatia Road Trip

    • August 10 2018

      I really enjoyed Airbnb Experiences and would definitely do it again! Just getting from Varadero to Havana was a pain. I think next time I’d rather just hang out in Havana for a few days. I really suffer in the heat, though. :( So hard to enjoy yourself when you’re feeling miserable.

  • August 30 2019

    Thanks for sharing your experience with us!

Leave a Comment

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.