I wanted to escape the monotony of resort life. So, I set out on a day trip to Havana. I was eager to rediscover the city’s rich history and vibrant culture. With Havana less than two hours away, it was the perfect opportunity to dive deeper into its storied past. Although I had visited before, something about this city kept calling me back. This time, I wanted more content, visuals, and, most importantly, a deeper connection to the local culture. Exploring Havana through a historical lens promised to reveal a side of the city I hadn’t fully experienced before. I explore its iconic classic cars and haunting ruins. I enjoy sipping a cocktail at Hemingway’s favourite bar.
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Booking a Local Tour in Havana: What to Expect
Wanting to avoid big tour companies like Sunwing and support a local operator instead, I carefully researched my options. Interestingly, I discovered that the company I selected—Ventas Holiplus—is the same local representative used by Sunwing for their tours. If you’re considering booking with them, here’s a little heads-up on the process!
Unlike automated booking systems, Ventas Holiplus handles everything individually, so expect a few email exchanges to finish your reservation. First, you’ll get a confirmation after booking. Then, they’ll send you a payment link. Once your payment is processed, you’ll get a digital coupon—your ticket for the tour. A pro tip: save the coupon in your text messages by sending it to your number. That way, you’ll always have quick and easy access to it, even without Wi-Fi.
This approach takes a little extra time. Nonetheless, it’s worth it to experience Havana through a more personal and local lens!
On the Road to Havana: The Journey Begins
With my bags packed and excitement building, I boarded the bus from my hotel, ready for a day of adventure. A clean and comfortable ride is always a great start; this one didn’t disappoint. Halfway to Havana, we took a well-timed break. We stretched our legs and sipped on a wealthy Cuban coffee. We also enjoyed some local snacks while taking in the scenic views.
Upon arriving in Havana, we first visited The Castillo de la Real Fuerza—the historic bastion fort on the western side of the harbour. Set back from the entrance. It borders the Plaza de Armas. It stands as a testament to the city’s colonial past. Interestingly, despite its imposing presence, the fort was ultimately ineffective. The location was too far from the water level. This allowed boats to follow the bay’s ledge undetected. Even so, as I stood before its weathered walls, I felt the echoes of Havana’s past. The city is built on stories waiting to be uncovered.
Antique Cars: A Timeless Havana Experience
I’ve been to Havana, and this is always my favourite part—the Antique Cars! These vintage beauties have been built, rebuilt, and lovingly maintained. Each car is a testament to Cuban ingenuity and pride. Every car owner takes meticulous care of their vehicle. Havana is one of the best places to explore in the back seat of a classic ride. It offers a unique and memorable experience.
You heard that right—you can book a tour with a private driver. You can cruise through the city in one of these iconic cars. It’s a must-do experience! But fair warning, as I learned firsthand—these cars are old, and some come with a little extra… exhaust fumes, haha! Still, there’s nothing quite like rolling through Havana’s streets in a piece of history. You feel the wind in your hair and the city’s vibrant energy around you.
Squares, Squares, and More Squares!
In Havana, the squares are the heart and soul of the city. They are places where locals and tourists gather to soak in the vibrant atmosphere. As we explored, we came across several, each brimming with life and history. It reminded me that this tradition isn’t unique to Havana; squares are central gathering spots in many parts of Cuba.
Havana boasts five significant squares. Each square serves as a meeting place where people come together to eat. They dance in the streets and socialize with friends. I love the openness of these spaces, framed by stunning historical buildings that tell their own stories. And, of course, the photo opportunities are endless! One of the most fascinating sights was the fortune teller in Plaza Vieja. She offered palm readings. She also posed for a photo in exchange for a small fee. I’ve even heard some locals call her Miss Havana—is that true? Either way, she adds to the city’s unique charm. She makes Havana’s squares more than just public spaces. They’re living, breathing pieces of Cuban culture.
Havana’s Historic Fortresses: Guardians of the Past
Havana is home to three impressive fortresses built to defend the city during the pirate era. The Fortaleza de San Carlos de la Cabaña stands out as one of the most distinctive. Perched on a hill on the port’s eastern side, this massive stronghold played a crucial role. It protected the city’s most vulnerable point.
Built between 1763 and 1774, this 18th-century fortress was designed to reinforce Havana’s defences. Today, it serves as both a historical landmark and a cultural attraction. Our guide mentioned that you’ll find museums inside showcasing Cuba’s military history. At night, the fortress comes alive with spectacular light shows. It offers a unique way to experience Havana’s past in a new light.
The Other Side of Havana: A Glimpse Beyond the Beauty
Old Havana is famous for its vintage cars and warm locals. The charming yet decaying buildings stand as reminders of its complex history. If this is your first time hearing about this reality, my apologies—but it’s an essential part of the city’s story. It’s one of the reasons I keep coming back. I return not just for the beauty, but I come for the truth. To see Havana as it truly is. Understanding how people live and to appreciate their resilience.
During my visit, I spotted what I thought was an abandoned building and pointed it out to a fellow traveller. The structure looked abandoned for years. Then, we caught a strong whiff of the open floor below. This scent made it clear that living conditions were far from ideal. We wouldn’t dare venture near it, let alone imagine calling it home. But then, to my surprise, I saw someone step out onto their precarious-looking balcony. The window coverings were falling apart, and the structure seemed barely stable. It was a stark contrast to the comforts of our Canadian homes. Even thinking about standing on such a fragile balcony was unthinkable.
Again, whether you agree with them or not, these are my personal reflections. Havana is a city of contrasts. Seeing its raw, unfiltered reality is just as important as admiring its colourful facades and vibrant culture.
A Quick Stop at Hemingway’s: The Cradle of the Daiquiri
As our tour ended, we had a short 15-minute window to explore. I had already captured a few images of Old Havana’s timeless beauty. I decided to step into El Floridita, the legendary bar called The Cradle of the Daiquiri. It was Ernest Hemingway’s favourite haunt.
At 4 p.m., the place was buzzing with tourists and locals. A lively Cuban band played, adding to the space’s vibrant energy. The ordering process was straightforward: place your order first, pay the gentleman in cash, and wait for your perfectly crafted daiquiri.
Since the dining room wasn’t open during our visit, I had a chance to glimpse its elegant and nostalgic decor through the doors.
With my daiquiri in hand, I raised a toast to Havana’s magic:
“¡A tu salud!” – To your health!
Until my next adventures
Roland
