4 Days in Havana, Cuba

Note: This post was written in 2017 when it was legal for Americans to travel to Cuba. For current guidelines, always check your local government regulations.

Cuba’s quite the hotspot these days. Now that Americans can travel to the island easier than ever before, it seems like everyone is planning a trip to see the country before it “changes.”

The thing is, Cuba has already started changing. In recent years, it’s become possible for Cubans to buy and sell cars and property, access the internet, and run private businesses. You can find the creative, entrepreneurial spirit popping up everywhere, from your English-practicing taxi driver to the trendy reservation-only restaurants.

It’s this transition period that I find so fascinating—seeing a place that’s been so cut off from the world become a part of it.

While it’s obviously important that Cubans gain access to the same technology, information and connection as the rest of the world, part of me can’t help but feel a bit sad that they too could soon become overwhelmed by digital consumption, the social media comparison trap, and collective noise that’s ever-present in an always on, always connected world.

In fact, it was the disconnection from technology that allowed me to connect with myself, my family, and my experiences in Cuba even more.

If you’re thinking of a trip to Cuba, I would say yes, it is the time to go. Not to see it before it changes, but to witness the changes as they’re happening now. Go to remind yourself of what it’s like to live without incessant technology; to make plans in person and keep them, to ask people questions instead of google, and to slow down to a simpler pace of life for a while.

Here’s what we covered over four days. Don’t miss my tips at the end! I’ll mention a few surprising little things that no one tells you.

Arriving in Havana, Cuba

My boyfriend and I flew JetBlue directly from JFK to Havana, arriving a few hours after my parents who were coming from Orlando. I stepped up to the immigration officer, handed over my passport and was told to step back while she called someone over. She handed my passport to the gentleman. He asked my name, then whistled to another man. That man came over took a flip through my passport, looked at me, and asked my name again.

Even though this all happened in a matter of seconds, it felt like hours. What could possibly be wrong? Was I going to end up in that scary little questioning room?

“You are meeting your mother and father?” he asked. “I am,” I said, now a little nervous that something went wrong for them.

He gestured for us to follow him, leading us through the crowd and pushing us to the front of the security line. Then he walked us over to where my parents were waiting for us. After another round of pushing us through the line ahead of everyone else, he led us outside and wandered off.

The four of us were certainly confused by this point but realized quickly that the airport manager was simply trying to help us. Now, after seeing how kind, generous, and helpful the Cuban people are this would come as no surprise.

We met up with one of the hosts of our casa particular, Angel, who drove us back to our place in his teal ‘53 Chevy and were met warmly by his wife who showed us the ropes. They also stocked the fridge with waters, rum, and beers. Perfecto!

Our apartment was located in Vedado, a residential/business district in Havana with modern restaurants, nightlife, and the famous Malecon—the wall on the sea. Every evening locals and visitors hang out on the Malecon to watch the sunset and drink rum. La vida es buena.

We spent the rest of the day exploring Vedado, including a walk to Cuba Libro, an English bookstore and local community space where we relaxed with a cafe bombon and a couple jugos de pinas.

Exploring la Habana Vieja

We pre-booked a full day tour with Havana Tour Company, which made things super easy. The day started with a walking tour of la Habana Vieja (Old Havana) learning about Cuban history, feasting our eyes on the grand architecture and colorful dilapidated buildings, and following the music down bustling, narrow streets.

After lunch (and a few mojitos) we piled in classic cars as drivers darted us around the outer parts of the city, stopping at the Plaza de la Revolution and the Hotel Nacional. There were four convertible cars in our group and the drivers were playing songs with their horns as if we were leading a parade. Their fun attitude, the warm sun on my face, and wind blowing in my hair made for a moment I’ll never forget.

The tour ended at the Hotel Nacional with daiquiris on the back lawn overlooking the sea. Our guide told us more about what life is like for young people in Cuba today, the changes that he’s witnessed throughout his life, and his personal dream of traveling the world himself.

Day trip to Viñales

The following day, Angel took us on a day trip to Viñales. We made the 3-hour journey (each way!) in his trusty Chevy, listening to his complete compilation of Michael Jackson tunes. We stopped on the way to eat ham sandwiches from a guy selling them on the side of the road.

I knew Viñales was beautiful, but it was truly breathtaking in person. Besides its mountainous landscape, the region is also known for producing the best Cuban cigars. For our first stop, we visited a tobacco farm and learned how the leaves are harvested, dried, and rolled. We were then invited to hang out with the farm’s charismatic owner, have some local coffee and rum (the best we had, for sure) and try a cigar. Not my thing usually, but hey, when in Cuba…

Next, we explored Cueva del Indio, a cave complete with a slightly Disney-esque boat ride on the underground river. Worth it? Sure, since there wasn’t much of a line. If there’s a crowd, I’d say pass.

For lunch, we ate overlooking the gorgeous mogotes (flat-topped mountains) and had one of best meals during our trip. Viñales was a lot more touristy than I expected, but not necessarily in a bad way. Even if you’re only staying in Cuba for a few days, a trip out there is certainly worth it.

Centro and More Old Havana

On our last full day, we walked an hour along the Malecon from our casa to la Habana Vieja, taking a route through Centro to get a closer feel for local life.

Once back in Old Havana we ate lunch at El Chanchullero. It was close to an hour wait but so worth it. The food was fresh, tasty and one of the cheaper meals we had. The waiter even brought us over a free round of Havana Club Añejo Especial for the table.

We rounded out the afternoon at the Museo de Bellas Artes before heading back to Vedado for dinner at El Cucinero and an evening of relaxing on our balcony, sipping rum and watching the nightly scene unfold on the Malecon.

Tips for your trip!

1. Bring snacks. Seriously. There aren’t really supermarkets to speak of. The stores that are available are government run and have next to nothing in them. Most bodegas only carry water, rum, and beer.

2. If you’re staying at a casa particular (private home) get the breakfast option if they offer it. Breakfast isn’t much of a thing in Cuba, so it’s difficult to find a place to eat in the morning. We ended up munching on trail mix we brought from home most days. See above.

3. Speaking of casa particulars, definitely stay at one! It’s so simple to book one through Airbnb these days. You’ll get a much better taste of local Cuban life. Plus it’s much cheaper, and better, than staying at one of the hotels.

4. Though English is still uncommon, people in Havana spoke it a lot more than I expected. Taxi drivers, restaurant employees, and even some folks just hanging out on the street chatting with us as we walked around.

5. The Cuban people are kind, welcoming, and eager to learn about you. Be eager to learn about them too.

6. Be prepared to wait in long lines, to have slow service, and embrace a no-rush lifestyle. Also be prepared to savor these moments, enjoy a relaxed attitude and have conversations without competing with a phone all the time.

7. There’s a booming modern-style restaurant scene happening (think craft cocktails and cool interiors) and many of these places require reservations so call ahead.

8. Havana wasn’t as cheap as I thought it would be. While it’s possible to spend much less than we did—we ate a nice paladares (private restaurants), had cocktails out, and didn’t bargain much when it came to taxis—we ended up spending about $60 per person per day (outside of accommodation and the Havana tour) in 4 days, which is still a bit more than I expected.

9. When museums say they close at a certain time, they mean it. The Museo de Bellas Artes closes at 5 pm, which doesn’t mean last entry at 5 pm, it means they start sweeping you out at 4:30.

Planning a trip to Cuba? Let me know what you’re excited about in the comments.