4 Lessons I Learned As a Solo Traveler In Cuba

Allow me to start off by metaphorically shouting from the rooftops: Cuba is an amazing country that you absolutely can (and should) venture to this year! I decided to go for Memorial Day weekend and am so glad I did. I stayed in Havana the whole time, which was a great place for solo travelers, but I’m hoping I can come back, visit some smaller towns, and convince some friends to go next time to share in the experience.

Since Havana is a unique destination that requires a bit of planning, I’ve decided to write two separate posts about it: this one, which hopefully inspires you to visit, and another that explains how to plan a successful trip (with a focus on American passport holders). If you already know you want to go, you can read that other post here.

Readers who are familiar with the blog will know that I typically organize my posts around the best attractions a city has to offer, but in this case, I’ll focus on four central themes that reflect what Havana is all about. Each theme will feature a handful of photos, and I’ll expand on the stories they tell. So grab a mojito or a café cubano and let’s jump right in!

I. North America is not a monolith.

You don’t have to leave the continent in order to find a completely different world.

I really started to get this sense after traveling to North American countries like Mexico and the Turks and Caicos Islands, but Cuba takes it to a whole new level. I think we Americans tend to get in the mindset that we have to travel to Europe, Asia, or beyond in order to really get the full experience of being “abroad.” But Cuba shatters that myth. If you believe culture shock is something to embraced rather than avoided, then you definitely need to consider this island nation located merely 90 miles south of Key West, FL. Furthermore, Cuba’s rich cultural blend of African, European, and Latin traditions make it feel like it might as well be a continent away.

As you can see, buildings in Havana have these beautiful, brightly-colored street-facing façades with ornate balconies. They may look old, but they play a key role in the community. At least in Havana Vieja, the “old town” of Havana, Cuban life thrives on these balconies. If you stay in Havana Vieja and your room is not on street level, you will almost be guaranteed to have one of your own; step out onto it and people-watch for a few minutes.

When I did, I noticed that many of the balconies were occupied with people sitting, knitting, reading, playing cards, etc. I realized that conversations weren’t confined to one floor or even one building; someone on the street would shout up to someone on a third or fourth-floor balcony and a reply was shouted back down. The entire conversation would go on like that until the person below continued on their way.

My favorite memory of the balconies features some schoolkids and a little old abuela up above. The kids would run up to the apartment building, ring a doorbell on street level, and the woman would appear on her fifth-floor balcony. A metal bucket on a string cascaded from her balcony down to the kids who would place a few pesos in the bucket. Within a few seconds, the bucket was reeled back up, and down it was sent again. The kids would reach in to discover what looked like home-made popsicles!

What made this even more endearing is that she didn’t have a sign or anything to advertise her ice cream for sale. You had to be in the know, and clearly there was a well-established system in place. After all, why use stairs when you can exchange words and items from right outside your living room?

The insides of buildings can also make Havana feel like another time and place. You will notice a lot of urban decay while exploring the city, but some of the city’s most historic landmarks are being restored, as evidenced by the scaffolding in this beautiful hall in the Presidential Palace (which currently houses the Museo de la Revolución).

And then there’s the cars. It’s true that a huge portion of cars on the roads of Havana are these 1940s, 50s, and 60s models that have been outfitted with new engines and other replacement parts. What started out as a response to embargoes over fifty years ago is now a famous tourist attraction. Many of these cars are actually taxis, so be sure to take one if you can! Riding through the city streets in a decades-old vehicle is a lot of fun!

Even businesses in Cuba looks different than their American counterparts. Many stores and food markets that cater to local residents like this one pictured above look quite barren compared to grocery stores or restaurants in the US; without a modern history of capitalism, Cuban businesses didn’t have as much of a need to dress up their establishments with fancy decorations, and that legacy is still very clear today.

II. Music matters.

Listening and participating are integral parts of the Havana experience.

It’s no surprise that Cuba has inspired musicians across the ages, from 20th century classical and jazz composer George Gershwin to current-day pop star Camila Cabello. The beats and rhythms of Cuban music are infectious and uplifting. Leave your earbuds at home and immerse yourself in the symphony that surrounds you in Havana!

Live music is impossible to avoid here. You’ll hear it in restaurants, bars, and on the streets. Even while walking along the city’s shoreline, you’re bound to run into musicians like this trombonist pictured above.

A band strolls leisurely by in front of the Morro Castle lighthouse.

Cabaret dancers strike a final pose at the end of a number.

A violinist steps outside onto the balcony of a bar to warm up for the next song her band is about to play inside.

Last but not least, this ended up being my favorite musical experience in Havana precisely because I got to participate. On my last night in the city, I ended up eating dinner at a random paladar near Calle Obispo, where this band pictured above was performing. Since dinner is eaten quite late in much of the Latin world, the restaurant was almost empty when I arrived, so the main singer invited me to dance while I waited for my food. She then handed me her maracas and had me play for a song or two. It was a great experience to be welcomed into their band so quickly!

After that, I informed them that I know how to play the violin, so the guy with the fiddle handed me his instrument. The only question was: what would we play? I didn’t know any Cuban songs, and I wasn’t sure what songs they might be familiar with. We landed on a compromise, a Latin song that every American knows: Despacito! It was so much fun to pick up the violin and just play in such a carefree environment, and the whole experience of being invited to perform with them really exemplified the friendliness that Cuban people are famous for.

Do you recognize this bridge from another Spanish pop song they performed that night?

III. Embrace the lack of internet.

You’ll make more friends here if you do.

As I describe in my other post, internet in Havana is still extremely limited. Although you probably should login to WiFi once or twice to let family and friends know you arrived safely, I highly suggest you make peace with the fact that you’ll basically be disconnected in Cuba.

A smartphone is much less distracting in airplane mode, which helped me engage more fully with the sights and sounds of Havana. That’s reason enough to embrace going off the grid, but I am convinced that the lack of internet also encourages everyone to be more outgoing. It is surprisingly easy to meet both locals and other travelers in Havana and to have meaningful experiences with people you’ve only known for a few hours or less.

This is especially the case in bars and restaurants. Americans should eat in privately-owned restaurants called paladares not only to help local business owners, but also because they are a great place to meet travelers from all over the world. Pictured below is a plate of ropa vieja (traditional Cuban dish of shredded beef) that I ordered at a paladar on Paseo de Martí.

When I arrived, there was only one other guest in the restaurant. I struck up a conversation with him and learned that his name was Tiago and he was from Portugal. I had a good time discussing my recent trip to Lisbon with him as well as our impressions of Havana. At the end of the meal we parted ways, but it was a great conversation that was refreshingly uninterrupted by messages, notifications, and social media.

Another great time to meet travelers and locals is during breakfast in your casa particular (or Airbnb). As you can see above, the breakfast that was served in my casa was fresh and appetizing (and cheap: only $5 including an omelet and ham not shown). Each morning, I got to chat with the owner of my Airbnb, his employees who prepared breakfast, and two other guests from Brazil. Since I saw all of these people every morning, it was easy to really connect with them and follow up on how their previous day went.

So that covers restaurants; let’s talk about bars. There are a lot of great bars throughout Havana, but probably the most famous one is El Floridita. It was a favorite hangout spot of Ernest Hemingway and their speciality is daiquiris (go for a regular or fruit-flavored one; the “Hemmingway daiquiri” is really bitter and honestly nasty).

As it turns out, this was another prime location to make some new friends. There were clearly tourists from all over the world crowding inside, and I ended up talking to a couple seated next to me who were visiting from New Jersey. We hit it off, bonded over how bad the Hemingway daiquiris were, and ultimately decided to explore on foot together for the rest of the afternoon.

From El Floridita, we walked three or four miles inland and eventually ended up at the Cementerio de Cristóbal Colón (Colon Cemetery), which brought us through some truly local neighborhoods and suburbs. Along the way, we passed by the José Martí Memorial pictured above.

By the time we reached the cemetery, we were exhausted and all agreed that cabs back to our Airbnbs and a few hours of rest were sorely needed. The two of them asked if I was interested in meeting up for dinner later, and I said sure! We agreed on a time and a restaurant, but without working phones, there was no guarantee that we’d successfully meet up. At dinner time, I made it to the restaurant early, waited, and…

They ended up making it too! Can you believe a bunch of millennials successfully met up without working phones? It was quite an accomplishment! I ran into my Brazilian housemates at the casa and invited them as well, which is why we ended up with a group of five. The place was called La Bodeguita del Medio, another famous bar/restaurant that’s known for their mojitos. I ordered the lobster, which was really tasty and only $22.

As you can see, Cuba’s current lack of internet connectivity makes it an especially good place to meet like-minded travelers. It’s important to recognize that locals don’t have affordable access to the wealth of online information and opportunities that we take for granted, but this is the reality of life in Cuba for now. For visitors like me who spend hours each day in front of screens, Havana can be a breath of fresh air. Go (almost) cold turkey, strike up a conversation with a stranger, and enjoy everything Havana has to offer!

IV. This is the Caribbean.

You might encounter a tropical storm, but this doesn’t have to ruin your trip.

If you’re unlucky, a tropical storm may pass over Cuba during your trip. And when it rains here, it pours. Bring an umbrella from home if rain is on the forecast (as they are a bit hard to come by in local shops), and be aware that hurricane season is June to November.

The downpours never lasted more than a few minutes, so I ended up exploring quite a bit of the city on foot in between rain spells. Under cloudy skies, cars speed by on the Malecón (Havana’s main oceanfront drive) between La Habana Vieja in the east and newer resorts and apartments in the west, pictured above.

However, even though the forecast predicted rain and clouds for my entire trip, it wasn’t entirely accurate (and the weather here can change in an instant). Thankfully, I got one full day of sun! An extra bottle of sunscreen is never a bad idea, no matter how rainy the weather is predicted to be.

And of course, when there are clouds, there’s bound to be a silver lining (or a rainbow).

Low-lying rain clouds can also make for some amazing sunsets. Rooftop bars and balconies are the best places to try and catch one.

I’ve been on quite a few weekend trips this year, but I must say that so far Havana has been my favorite. It’s not for the faint of heart or the inexperienced traveler, but if you’re willing to give it a try, you’ll come away with a unique experience that you will remember vividly for the rest of your life. You’ll probably also be antsy to go back soon; I know I am!

If you’re an American citizen and I’ve convinced you to go (or at least consider it), there are a number of things you need to know before you hop on that plane. From applying for a visa to choosing US government-approved lodging options, I explain it all right here. If you’re not a US citizen, some of the information in my other blog post may be relevant to you, but you probably are fortunate enough not to be subject to the restrictions I describe there. Whether you’re from New York, São Paulo, or a small town in heartland, you will definitely leave “half of your heart” in Havana!

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This Post Has 2 Comments

  1. Anne / FinnsAway

    Nice read, Cuba for sure is amazing! Haven’t been there yet, but planning to go soon, and travel around for a bit longer time 🙂

    1. caffeinated_wanderer

      Thank you, Anne! It was definitely an amazing experience and I hope to go back and see more soon! Maybe Viñales?

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