The minute we landed in Havana, we drifted back to the 1950s. Due to the U.S. embargo placed on the country following the Cuban Revolution, the country receives limited international trade, leaving the majority of goods outdated. This is apparent from the vintage vehicles, to the spices used in local food, and limited wifi. As Anthony Bourdain said, “Yes, the future is here. But the past too is everywhere. The buildings, the cars, the gears of the whole system are still largely stuck in time.” This blend of rich history and rising urban culture is on display to tourists in the buzzing city of 2 million inhabitants. From the local uptempo music reverberating in the streets, vibrant colonial architecture, and warm tropical breeze, we couldn’t wait to unplug and explore the sights of Cuba’s capital for ourselves.
Touring Habana Vieja
The most iconic neighborhood in Cuba known for its vintage cars and candy colored buildings is Habana Vieja, or Old Havana. Named a Unesco World Heritage site, its beauty is apparent with the Spanish colonial buildings and cobble stone plazas. We got lost walking through the many small streets as old classic cars and bicycle taxis zipped by. We stopped by to check out Plaza Vieja, the old square, and Plaza de la Catedral, cathedral square. Each of these courtyards highlighted the differences of the original vs restored architecture of the town.

Walk down El Malecón
Stretching 5 miles (8km), this busy 6 lane, seaside avenue stretches along the Northern coast to the mouth of the Havana harbour. It’s a quintessential promenade where locals and tourists alike take in the breathtaking Havana sunset (literally at times from the smog, those 60+ year old caddys kick up a lot of dust!).


We passed by musicians and historical monuments as we meandered along. Eventually, we haggled our way for a 6 person cab to head home. This was stressful along the busy roadway, so we recommend walking back into one of the nearby plazas to catch a ride.

Visit the Museo de la Revolución
Ditch your textbook comprehension of the Cuban revolution and tour the Museo de la Revolución. Set in the old Presidential Palace, the building itself is historical, constructed in the early 20th century and home to 40 years of Cuban presidents. The walls are replete with revolution-era artifacts and bullet holes still intact from an attempted assisination of Fulgencia Batista in 1957.
It was truly interesting to visit the museum as a group of Americans, as the museum is curated through a Cuban lens. The exhibits pay homage to guerilla leaders Che Guevara and Fidel Castro and provide insight on events leading up to, during and immediately following the Cuban Revolution. Rooted in the Cold War, the U.S. backed the right winged government of Fulgencia Batista, who was overthrown by Castro’s regime in 1959. The museum displayed a large amount of historical propaganda, and gave us a new perspective of U.S political antagonism. While at times we felt uncomfortable as Americans, we were glad to have learned a new viewpoint that was omitted from our Western textbooks.
Eat at San Cristóbal Restaurant
To start our night out, we sauntered our way through the vibrant streets of Central Havana, to arrive at the San Cristobal Restaurant. This paladar, or restaurant, is renowned not only for its modern Cuban dishes, but also celebrity dine-ins. The most famous and historical being Barack Obama, who was the the first president to visit Cuba since Calvin Coolidge in 1928. We made sure to make a reservation at the restaurant a few days ahead to dine as the stars do.
To our surprise, there was absolutely nobody else in the restaurant when we arrived. When we checked in, our hostess asked where the remainder of our group was because we had accidentally booked out the entire place! A translation mix up to reserve a table “for six people” was heard as for “46 people!” Luckily, the owner quickly realized the mishap, and the entire staff had a huge laugh. Our group was mortified to say the least, and ordered tons of foods and drinks to try to make up for the full buy out. By the end of the night we were cackling at our mistake over drinks and cigars with Chef Carlos and staff. Vic passed the baton to Zach, who spoke fluent Spanish to make our reservations for the rest of the trip!
Check out Fábrica De Arte Cubano
Listed on Time magazine’s greatest places of 2019, this converted warehouse does not disappoint for a night out. We hopped in a vintage taxi to the Vedado district to find the Cuban Art Factory. This three floor art gallery and night club is filled with multimedia contemporary design, bars, cafes, live music, and a buzzing dance hall. For a Sunday night, we explored until the museum closed at midnight, then danced our way to the salsa party which kept going past 3AM.
Sip a mojito on Ernest Hemingway’s old roof top!
No visit to Cuba is complete without having a refreshing mojito, or two! What better place to escape from the heat and enjoy this classic cocktail, than at the Hotel Ambos Mundos, where Hemingway resided for 7 years in 1932-1939. The Nobel prize winner for his literature is often associated with Cuba for its influence throughout his writing.
While Hemingway lived on the 5th floor, we made our way to the rooftop to take in the same views that were his muse. The panoramic sights of the city are incredible from this vantage point and showcase both the colonial architecture of Old Havana and the glistening waters of the harbour. We ordered a minty mojito pitcher to share and ice cold water to quench our thirst. This was the afternoon break we needed before making our way back into the bustling city.
Exploring Havana was truly a unique experience. With only 2 days to wander, we were able to soak in the rich history, vibrant culture, and create lasting memories by visiting the range of sights on our above itinerary. The city stuck in time offers an untouched lifestyle that must be experienced first hand. If you can secure a tourist visa, we recommend you add Havana as your next sightsee.

P.S. On our last day in Havana, we decided to get out to the countryside to explore more of Cuba. To learn more about our full day excursion, check out our post about Viñales valley.
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