Epic Weekend in Havana: A 2-Day Cuba Travel Itinerary

Havana is a dream destination for any traveler. Ever heard that “just 2 days is not enough to see all it has to offer”? Well, challenge accepted! While you can’t squeeze in ALL the sights of Havana in just a weekend, you can definitely hit most of the highlights and soak up the Cuban spirit and rich history. Oh, and trust me – having a blast is non-negotiable in this city packed with cool vibes, awesome people, and refreshing mojitos. Let’s dive into your epic itinerary for an unforgettable weekend in Cuba!

Weekend in Havana Travel Itinerary – Day One

• 🏛️ Capitolio Visit
• 🕍 Cathedral Square Shenanigans
• 🍹 Mojito Time at Bodeguita Del Medio
• 🚶‍♀️ Strolling Through Habana Vieja
• 🌇 Rooftop Sunset Dreams
• 🥂 And Then, Mojitos

Capitolio Visit

Inaugurated in 1929, El Capitolio was built to wow — and it still does. But more than just a pretty facade, it’s a living link to Cuba’s sugarcane fortune age. Step inside, grab an audio guide, and drift through rooms infused with bygone sophistication.

A Guided Stroll Through History

Entrance to the Capitol costs 10 CUC (≈ 10 USD) and is only possible with a guided tour by a “guia,” a local who adds a touch of warmth and authenticity to the site’s historical significance. As you move through the Capitol’s vast corridors and chambers, these narratives unravel the layers of Cuban life, past and present, with passion that only a local can provide.

Cathedral Square: Where Columbus Sleeps and Bells Chime

Shall we salsa over to Plaza de la Catedral? This square is ancient elegance, a taste of Spain amid Cuba’s colorful chaos. Step into the Cathedral of St. Christopher – it’s not every day you get to share a pew with Christopher Columbus’s remains. And please do climb that tiny tower!

Cost to climb the tower: 1 CUC (just over a dollar)

Bodeguita Del Medio: Hemingway’s Mojito, Anyone?

 If its walls could talk, they’d probably slur something about the best mojitos in the world. And that’s where you can have lunch.It’s tourist-trodden, sure, but have you really been to Havana if you didn’t clink glasses with Hemingway’s ghost? 

A Stroll Through the Enigmatic Habana Vieja

Amble along the streets of Habana Vieja, the city’s core. Here, each turn leads to an epoch, a style, an era. The architecture is a symphony, from the colonial to the baroque, telling a story in every crevice. It’s a living museum, a confluence of cultures and contraries, where time hasn’t passed but pirouetted.

Rooftop Romancing with Havana’s Sunset

Finish off your first Havana day with a rooftop sunset that’ll make even the most jaded traveler weep. Just imagine sipping on a mojito while the sun kisses the skyline goodbye—yeah, it doesn’t get better than this.

End your architectural date on a high note, literally. Havana’s skyline is best seen with a cocktail in hand. If there’s one place the sunset is lethal, it’s here – twisting and turning the city gold, until it’s tres leches cake. The Capitol shines.No place discloses the magic of Havana’s skyward canvas quite like its rooftops.

And Then, Mojitos

It’s time to wind down with a Mojito in hand at a cozy bar. Because, after such an action-packed day, you’ve earned that refreshing hit of minty goodness.

There you have it – Day 1 in Havana, where breakfast fuels colonial explorations, and everything ends with a Mojito. Can’t wait to see what Day 2 of our Havana weekend itinerary brings, can ya?

Weekend in Havana Travel Itinerary – Day Two

• Time Travel in Old Havana in a vintage convertible car
• Lunch at Plaza Vieja
• Cultural Cocktail at Plaza de San Francisco de Asís
• A Casual Stroll Along Paseo Del Prado
• Night Moves at Malecon

• Bonus – The Trio of Fortresses:
  • La Fuerza Fortress
  • Complex La Cabaña
  • El Morro

Havana might be huge, but its heart is in the streets of Old Havana. In a city that seems to dance even when it walks, every step is a chance to connect with the past and celebrate the now. Ready to dive into day 2 of an epic weekend in Havana?

Cafe Con Leche: Havana’s Morning Ambrosia

The second act is not without its fuel. Havana runs on cafe con leche – this isn’t a Starbucks, this is Cuba, and the java here is as exquisite as the old baristas who serve it. Find any local cafe and take a seat where you can watch the world whirl by. As you sip, Cuban omelets and sweet guava pastries will grace your table, balancing the bittersweetness of your morning mug.

Step 2: Strolling Through Time in Old Havana

No trip to Havana is complete without a thorough exploration of its historical heart, Old Havana. This is where centuries-old stories are etched into the very walls of the colonial architecture. I’m talking palaces that once held the sway of Spain, cobblestone streets that whisper the names of forgotten poets, and the kind of faded grandeur that’s so cinematic, it feels like you just stepped into a vintage film reel.

Make sure you don’t just see Old Havana—experience it. Engage with the locals. Everywhere you turn, you’ll find little slices of Cuban life that are as vibrant and multi-layered as the city’s culture. 

Lunch at Plaza Vieja – The Old Square that Feels New

Plaza Vieja’s got a story to tell—one of centuries and square footage. Once called Plaza Nueva, it boasts a sprinkling of neo-classic and baroque architecture that’s cooler than the other side of the pillow. 

Plaza de San Francisco de Asís: The Cultural Convergence

Welcome to Plaza de San Francisco—where the past and present collide in a chorus of colors and aromas. This iconic plaza is more than just a pretty picture. It’s a living entity, pulsating with energy from the lively markets, echoing historical anecdotes shared by the architecture, and the rhythmic beats of local musicians.Have an awesome lunch at one of many restaurants on the plaza or vicinity.

The Artistic Artery of Havana

Paseo del Prado: An Artistic Interlude

Belly full? Awesome, now stroll down Paseo del Prado (A short walk from Plaza de San Francisco is). Paseo del Prado is a broad boulevard shaded by the verdant canopy of spreading trees. It’s a natural haven from the Caribbean sun. The Paseo is not just a beautiful street, but a living art gallery. Here, you’ll find a mix of architectural styles that offer a crash course in Cuban art history. And the savvy traveler knows that art is not just confined to galleries but lines these streets in myriad forms.

Keep your eyes peeled for the murals scattered throughout the city, for every brushstroke tells a different story. And if you crave a live performance, the lively rumba dancers at Callejon de Hamel on Sundays are not to be missed!

Havana travel itinerary:Malecon, Late Night with the Locals

Don’t even think about bedtime. Not here. You’re in Havana, and the night has promises to keep. Follow the locals to the Malecón, where dreams and waves collide.

The Malecón is Havana’s soul laid bare, daring you to understand and appreciate its complexity. 

Bonus: The 3 fortresses

La Fuerza fortress

La Fuerza fortress, easily reachable from Old Havana. Locals might puff up and call it the Castle of Royal Power, and who are we to argue? This ancient behemoth doesn’t have a peer in age in both Americas.

What’s a fortress without a moat? Yep, La Fuerza still rocks its water-filled ditch. Inside, tour guides spill tales of pirate sieges that Havana scoffed at. Oh, and there’s a museum packed with boat models and a treasure room straight out of your pirate fantasies.

Complex La Cabaña

Leaving La Fuerza, wave down a cab because, honey, we’re tunneling under water next, heading to the La Cabaña fortress complex. This baby spans 700 meters and is strutting its 240-year-old stuff. Every time you hear the age of anything in Cuba, it’s a jaw-drop moment – how is it all still so darn majestic?

Visit in the AM to dodge the tourist jam. Find a perch, sip some air, and contemplate life or what’s for lunch. The view’s a knockout – ocean vistas wrapped in the embrace of La Cabana’s robust arms.

Last Fortress Standing: El Morro 

Feel refreshed? Onward to the lighthouse at El Morro fortress we go – still working, by the way. Brace for the view at the top: a swoon-worthy blend of azure waves and the sun-kissed stone of neighboring rooftops. Bust out that camera, ’cause this scene’s begging to be Instagrammed. El Morro, a Havana icon, has been playing gatekeeper to the harbor for 384 years, flaunting evening cannon firings for the touristy crowd.

Havana Things to do to Add to Your Havana Travel Itinerary

1. Cruise in Style 🚗

First up, imagine yourself cruising in a glossy convertible classic – a 1950s gem that’s more than just a ride; it’s your time machine to Havana’s golden era. Sure, it screams tourist, but guess what? It’s the kind of touristy you won’t regret.

2. Cheers to the Cuban Way 🍹

Next, dive into the heart of Cuba with a mojito in hand, or perhaps a Canchanchara if you’re feeling adventurous. These aren’t just drinks; they’re your first salsa lesson in liquid form. And boy, do they know how to get the party started!

3. Sunset Views for the Soul 🌇

Ever watched a sunset that makes you want to write poetry? Havana’s rooftops offer you that soul-stirring spectacle. It’s not just a visual treat; it’s a reminder to pause and soak in the beauty of the moment.

4. A Walk to Remember 🚶‍♂️

Take a stroll through Havana’s colorful streets, where every corner tells a story, and every dilapidated facade holds the whispers of the past. This place isn’t just photogenic; it’s a photographer’s love affair with history and charm.

5. Connect with the Heartbeat of Havana ❤️

What’s Havana without its people? They aren’t just the city’s heartbeat; they’re your guide to the real Cuba. Share a smile, a story, or a dance move. Who knows? You might just leave with friends for life

6. Lobster on a Budget? Yes, Please! 🦞

Havana offers a rare luxury – the chance to indulge in the freshest, juiciest lobsters without breaking the bank. It’s not just a meal; it’s a feast for your taste buds.

7. Smoke it like Hemingway

Whether you’re a smoker or not, witnessing the art of Cuban cigar making is a must. It’s not about the smoke; it’s about the craft, the tradition, and if you’re lucky, a moment of zen.

8. Market Madness 🍉

Immerse yourself in the local scene with a trip to the markets. This isn’t your usual grocery run; it’s a cultural deep-dive. Engage, taste, and maybe even haggle a little. It’s all part of the experience