Transparency & Disclosure
At this time, there are restrictions for Canadian travellers and significant logistical challenges on the island; today’s blog is meant to keep our wonderful Cuban memories alive and provide a roadmap for when the doors to this vibrant culture fully swing open again.
Professional Update (February 12, 2026): Global Affairs Canada has officially raised the risk level to “Avoid Non-Essential Travel” due to worsening shortages of fuel, electricity, and basic necessities. As a result, all major Canadian airlines (Air Canada, WestJet, Sunwing, and Air Transat) have temporarily suspended upcoming flights to Cuba through at least April 30, 2026.
This guide serves as a logistical archive and a cultural tribute until stable travel resumes.
TL;DR: Escape the monotony of resort life with this 24-hour immersion into Havana. From cruising in 1950s classic cars to exploring 18th-century fortresses and sipping daiquiris at Hemingway’s favourite haunt, this guide reveals the duality of Cuba’s capital—where beauty and decay coexist in a vibrant dance of resilience.
Article Intent This guide provides 2026 travellers with a cultural and logistical roadmap for a day trip to Havana. It prioritizes supporting local operators, historical photography of colonial ruins, and authentic local encounters, verified through first-hand experience and professional visual storytelling.
Transparency Matters. I chose to book this experience independently to escape the “Sunwing bubble” and support local Cuban entrepreneurship. This post contains affiliate links; if you book through them, I may earn a small commission that helps fund my next photography journey at no extra cost to you. ¡Gracias!
The “Slow Travel” Experience: Why I Return to Havana
What draws me back to Havana isn’t just the pastel façades or the music echoing through narrow streets. It’s the duality—the rhythm and the stillness, the pride and the struggle. Havana teaches you that history doesn’t just live in museums; it breathes in every cracked wall and every story told over a daiquiri. This journey was about moving past the “tourist lens” to see the city as it truly is.
Consult my Cuban logistic map to see if your resort is in the “I can make it to Havana” for a day.
2026 Traveller’s Checklist: Havana Essentials
- Connectivity Tip: Wi-Fi is still a luxury here. Save your tour coupons and maps in your text messages or as offline screenshots before you leave the resort.
- Photography Gear: A 35mm prime lens is the “storyteller’s lens” for Havana’s narrow alleys. Bring a circular polarizer to manage the harsh Caribbean sun reflecting off the classic car chrome.
- Currency & Cash: Always carry small bills in CAD or USD for tips and quick stops like El Floridita.
***NEW Health Care Insurance***
While you might have skated by with just your provincial health card in the past, 2026 is the year of the paper trail. To avoid a stressful start to your trip, print a copy of your private travel insurance policy that explicitly lists ‘Cuba’ as a covered destination. Make sure it includes emergency medical evacuation, as this is a non-negotiable requirement for Cuban immigration right now.
1. Booking Local: Supporting the Cuban Economy
How do I book a tour without using the big resort companies? I wanted to avoid the massive bus tours and support a local operator instead. After researching, I selected Ventas Holiplus.
What to Expect with Local Bookings
Interestingly, Holiplus acts as the local representative for many larger agencies, but booking with them directly allows for a more personalized touch.
- The Process: You’ll receive a confirmation email, followed by a payment link, and finally a digital coupon.
- Pro Tip: In a country where Wi-Fi can disappear in an instant, having that coupon saved to your phone’s local storage is a lifesaver.
2. On the Road: The Bastions of Colonial History
The two-hour drive from the resorts is a transition from manicured lawns to raw landscape. Our first stop was The Castillo de la Real Fuerza, the historic bastion fort guarding the harbour.
The Castillo de la Real Fuerza
Standing before these weathered walls, you feel the echoes of a colonial past. Interestingly, the fort was historically ineffective because it was set too far back from the water’s ledge, allowing ships to slip by undetected. It’s a reminder that Havana is a city built on beautiful, sometimes flawed, stories.
3. Antique Cars: A Timeless Havana Experience
Is a classic car tour worth the hype? Absolutely. These vintage beauties are more than just cars; they are a testament to Cuban ingenuity and pride. Each vehicle has been built, rebuilt, and lovingly maintained for decades.
Cruising in a Piece of History
There is nothing quite like rolling through Havana’s streets in the back seat of a 1950s convertible.
Photo Tip: For the best shots, ask your driver to head toward the Malecón during the “Blue Hour” to capture the city lights reflecting off the car’s hood.
A Note of Realism: These cars are old, and you will encounter some exhaust fumes!
4. The Five Squares: The Living Heart of the City
In Havana, the squares are the soul of the community. From Plaza de Armas to Plaza Vieja, these are the spots where the city’s energy is most infectious.
Meeting “Miss Havana”
In Plaza Vieja, I encountered the famous fortune teller—locals call her Miss Havana. She offers palm readings and poses for photos for a small fee. She is a living piece of Cuban culture, adding a layer of mystery and charm to the stunning historical architecture.
5. Havana’s Historic Fortresses: Guardians of the Past
Havana is home to three impressive fortresses built to defend the city during the pirate era. While they no longer hold back invaders, they now serve as the best vantage points for photographers looking to capture the city’s scale.
Fortaleza de San Carlos de la Cabaña
Standing out as the most distinctive, this massive stronghold is perched on a hill on the port’s eastern side. It played a crucial role in protecting the city’s most vulnerable point—its landward entrance.
2026 Update: At night, the fortress comes alive with spectacular light shows and the 9:00 PM Cannon Shot Ceremony (El Cañonazo de las Nueve). Actors in full 18th-century Spanish military regalia reenact the tradition of signaling the closing of the city walls. It is a hauntingly beautiful way to experience Havana’s past in a new light.
The History: Built between 1763 and 1774, this 18th-century fortress was designed to reinforce Havana’s defences after the British successfully captured the city in 1762. Today, it stands as one of the largest colonial fortresses in the Americas.
The Experience: Inside, you’ll find museums showcasing Cuba’s military history, including an exhibit dedicated to Che Guevara.
6. The Other Side of Havana: A Glimpse Beyond the Beauty
Old Havana is world-famous for its vintage cars and the warmth of its locals, but the charming yet decaying buildings are more than just backdrops for a photo—they are the scars of a complex, ongoing history. If this is your first time hearing about this reality, my apologies, but it is an essential part of the city’s story and one of the core reasons I keep coming back. I return not just for the beauty, but for the truth. To see Havana as it truly is means acknowledging the resilience required to live within its “frozen” timeline.
Witnessing a “Slow-Motion” Collapse
During my visit, I spotted what I thought was an abandoned building and pointed it out to a fellow traveller. The structure was a skeleton of its former self, seemingly untouched for years. However, as we walked closer, we caught a strong whiff of the open floor below—a scent of damp earth and neglect that made it clear living conditions here were far from the resort standard.
We wouldn’t dare venture near it, let alone imagine calling it home. But then, in a moment that stopped me in my tracks, I saw someone step out onto a precarious-looking balcony. The window coverings were tattered, and the entire structure seemed to defy gravity. It was a jarring contrast to the comforts of our Canadian homes, where a single crack in a foundation causes alarm. Here, life continues on the edge of a fragile balcony because there simply is no other choice.
2026 Reality: Resilience Amidst the “Polycrisis”
In 2026, the duality of Havana has sharpened. While new luxury hotels like the Torre K rise in the distance, the historic centre faces what experts call a “slow everyday collapse.” Severe fuel shortages and power outages that can last over 20 hours have become a daily test of the Cuban spirit. Yet, even as the walls crumble, the social fabric remains incredibly tight.
You’ll see it in the way neighbours share a single working flashlight during a blackout, or how a street game of dominoes continues with laughter even as the sun sets on a darkened street. My goal as a photographer is to capture this—not as “poverty porn,” but as a tribute to human endurance. Understanding how these families navigate a city where 46% of the buildings require emergency action is the only way to truly “see” Havana.
Photography Note: When shooting these more sensitive areas, I always prioritize the dignity of the residents. If someone is on their balcony, I lower my lens or ask for a nod of consent. Capturing the architecture of decay is one thing; capturing a person’s struggle requires a level of respect that transcends the “perfect shot.”
Why the “Truth” Matters for Travellers
Whether you agree with the politics or not, these are my personal reflections. Havana is a city of brutal contrasts. Seeing its raw, unfiltered reality—the smell of the street, the precariousness of the homes, and the unwavering pride of the people—is just as important as admiring its colourful facades. It reminds us that “Slow Travel” isn’t just about taking your time; it’s about making your time count by witnessing the world without the filter.
7. A Quick Stop at Hemingway’s Haunt
Where is the best daiquiri in Havana? As the sun began to set, I stepped into El Floridita, the legendary bar known as the “Cradle of the Daiquiri” and a favourite of Ernest Hemingway.
The El Floridita Experience
At 4 p.m., the energy is electric. A live band plays as the bartenders expertly craft dozens of daiquiris at once. The process is simple: pay cash, wait for your drink, and soak in the history. It’s the perfect spot to raise a toast—¡A tu salud!—to the magic of this city.
El Floridita,
Why I Love Havana
What draws me to Havana isn’t just its pastel façades or music echoing through narrow streets. It’s the duality — the beauty and decay, the rhythm and stillness. Havana has a soul that never fades. It teaches you that history doesn’t just live in museums; it breathes in every cracked wall, every song, every story told over a daiquiri.
Frequently Asked Questions about Visiting Havana
Most Varadero resorts are about two hours from Havana by car or bus.
Yes, Havana is generally safe during daylight hours, especially in popular areas like Old Havana and the main squares.
Support local operators like Ventas Holiplus for personalized experiences.
A ride in a classic car, visiting El Floridita, and exploring Plaza Vieja for its music, art, and people.
November to April offers pleasant weather, while May to October is warmer with occasional rain.
About the Author
Written and photographed by Roland Bast, a Canadian travel photographer and visual storyteller based in Ottawa.
Member of TMAC (Travel Media Association of Canada). Roland captures authentic travel stories from across Canada and beyond, blending culture, history, and people through photography.
With my daiquiri in hand, I raised a toast to Havana’s magic:
“¡A tu salud!” – To your health!
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