How To Spend A Weekend In Cuba

A 72-hour sojourn in Havana presents a delightful abundance of possibilities, ensuring that every moment is filled with enriching experiences. The allure of this captivating city lies in its ability to seamlessly blend diverse passions. Whether your heart yearns for delving into the depths of history, immersing yourself in the vibrant world of art and architecture, or indulging in the pleasures of fine dining, savoring exquisite cigars, and admiring the timeless elegance of classic cars, Havana effortlessly caters to your desires. In the heart of the Cuban capital, you’ll discover experiences that offer a profound and vivid sense of what makes Cuba so uniquely enchanting. Embark on a journey with us as we present five distinct itineraries, each promising an unforgettable weekend in Havana, tailored to different interests and tastes.

#1 Havana Highlights

This itinerary provides a comprehensive and delightful taste of Havana’s multifaceted charm. It meticulously focuses on the most captivating sightseeing opportunities, the most delectable culinary experiences, and the most enriching cultural highlights, ensuring a well-rounded exploration of the city. Furthermore, it thoughtfully allows ample time for you to unwind and let your hair down in the evenings, embracing the vibrant nightlife that Havana has to offer. Prepare to be swept away by the energy and vibrancy of this extraordinary city.

Upon your arrival at José Martí International Airport, begin your Havana adventure with a classic Cuban lunch at El Aljibe. Savor the traditional flavors before checking into your accommodation. Subsequently, immerse yourself in a comprehensive sightseeing overview aboard the HabanaBusTour, which gracefully circles the entire city, making convenient stops at all the must-see highlights. From the iconic Plaza de la Revolución, a site of historical significance, to the majestic Castillo Los Tres del Morro, a formidable fortress steeped in history, and the whimsical community art project known as Fusterlandia, where creativity knows no bounds, the bus tour offers a captivating introduction to Havana’s landmarks. Alternatively, elevate your experience by hiring a classic convertible car, accompanied by a knowledgeable chofer (driver), to follow the same itinerary. This personalized approach allows you to soak in the sights and sounds of Havana at your own pace. Continue your journey to the Museo Ernest Hemingway, the former estate of the Nobel Prize-winning author. Step into his world as you explore the grounds and learn about his life in Cuba. As the day comes to a close, indulge in a memorable dinner at the incomparable La Guarida, a paladar renowned for its exquisite cuisine and unique ambiance.

Dedicate your second day to exploring Habana Vieja (Old Havana), the city’s captivating colonial quarter. Make an early start to maximize your time in this UNESCO World Heritage Site, ensuring you witness as much of its splendor as possible. Concentrate your exploration around the main squares, starting with Plaza de Armas, where history comes alive amidst stunning architecture. Next, visit the Plaza de la Catedral, home to the magnificent Havana Cathedral, a masterpiece of Baroque architecture. Finally, immerse yourself in the vibrant atmosphere of Plaza Vieja, a beautifully restored square boasting an array of excellent paladares (private restaurants), offering authentic Cuban cuisine. Refresh yourself with freshly brewed suds at Fáctoria de la Plaza Vieja, a local brewery that captures the essence of the city. In the afternoon, venture to Parque Central, a bustling hub where the top draw is the Capitolio, the recently restored former Congress building. Marvel at its grandeur and architectural details before taking a leisurely walk along the sloping, tree-lined Prado (main boulevard), the city’s iconic promenade. Enhance your cultural immersion with a guided tour of either the Museo de la Revolución (Museum of the Revolution) or the Museo de Bellas Artes (Fine Arts Museum), two of Cuba’s most esteemed museums, each offering a unique perspective on the nation’s history and artistic heritage. As night descends, head to the Jazz Café to enjoy live jazz music, or experience the world-famous Tropicana cabaret, a dazzling spectacle of music, dance, and vibrant costumes.

On your final morning, take a leisurely stroll along the seafront Malecón boulevard, a historic esplanade that stretches along the coast of Havana. Soak in the breathtaking views of the ocean and the city skyline as you make your way to the iconic 1930s-era Hotel Nacional. Here, take time to savor a premium Cuban cigar and a refreshing cocktail at the patio bar, immersing yourself in the hotel’s timeless elegance and vibrant ambiance. Finally, bid farewell to Havana as you head back to José Martí International Airport for your departure flight, carrying with you cherished memories of your unforgettable weekend.

#2 Say You Want a Revolution!

Contemporary Cuba has been shaped inseparably by the Revolution, marking a pivotal chapter in the nation’s history. This period extends beyond the 1959 toppling of dictator-president Fulgencio Batista, encompassing the ongoing building of a new society. Regardless of your political stance, embarking on a pilgrimage of the revolutionary trail in Havana offers a fascinating journey through history. Witness firsthand the transformation of a nation and gain a deeper understanding of Cuba’s revolutionary spirit.

Fidel Castro, the iconic leader of the Cuban Revolution, claimed that the Revolution was profoundly inspired by Cuba’s National Hero, José Martí, a prominent figure in the 19th-century independence movement. Embark on your revolutionary tour in Habana Vieja at his birthplace: Museo Casa-Natal José Martí. This museum offers a glimpse into the early life and intellectual development of José Martí, allowing you to appreciate his profound influence on Cuban history. Then head to the nearby Museo de la Revolución, housed in Batista’s former Palacio Presidencial, for a complete profile on revolutionary history. Immerse yourself in the captivating narrative of the Revolution as you explore the museum’s exhibits, which showcase artifacts, documents, and photographs that bring the era to life. Don’t miss the Granma—the vessel that brought Fidel, Che Guevara & Co. from Mexico to launch the revolution. This iconic ship stands as a symbol of the Revolution’s audacious spirit and unwavering determination.

Day two is dedicated to exploring the Vedado district, a neighborhood that holds significant revolutionary landmarks. Your first stop is the Universidad de la Habana, where Fidel Castro pursued his studies and honed his intellectual prowess. Explore the university’s historic grounds and imagine the atmosphere of revolutionary fervor that once permeated its halls. Next, visit Museo Abel Santamaría, located in an apartment that served as a secret headquarters for Fidel’s revolutionary movement. Discover the clandestine operations and strategic planning that took place within these walls, gaining insights into the inner workings of the Revolution. There’s also the Hotel Habana Libre (the former Havana Hilton), a landmark that played a significant role in the Revolution. It was here that Fidel Castro established his headquarters after Batista fled, marking a symbolic shift in power. In the afternoon head to Plaza de la Revolución—the seat of government—to photograph the mural of Che Guevara, the iconic revolutionary figure whose image has become synonymous with the Cuban Revolution. Pay your respects to this legendary figure and contemplate his enduring legacy. Then, visit the Centro de Estudios Che Guevara, located opposite Che’s former home. This research center is dedicated to studying Che Guevara’s life, ideology, and contributions to the Revolution. End your day exploring Necropolis Cristóbal Colón, the sensational cemetery that serves as the final resting place for many revolutionaries. Marvel at the elaborate mausoleums and monuments that pay tribute to these individuals who shaped the course of Cuban history.

On your last day, explore Fortaleza de San Carlos de la Cabaña, a formidable fortress that stands as a testament to Havana’s rich military history. The forecourt outside this 18th-century fortress has displays from the 1962 Cuban Missile Crisis, a pivotal moment in the Cold War that brought the world to the brink of nuclear conflict. Reflect on the historical significance of this site and contemplate the delicate balance of power that shaped the era. Nearby is Casa-Museo del Che, the comandante’s former headquarters. This museum offers a glimpse into Che Guevara’s life and work, showcasing his personal belongings, documents, and photographs.

#3 Cars, Cigars, and Cabarets

To kick off this itinerary, you’ll be met on arrival at Havana’s José Martí International Airport by a pre-arranged classic convertible car with chofer, which you’ll use throughout your visit. This personalized service ensures a seamless and stylish arrival, setting the tone for an unforgettable Havana experience. Begin your culinary exploration with a lunch of roast chicken in orange-garlic sauce, with rice, black beans and all the trimmings at El Aljibe, then follow the highlights tour in Itinerary #1, including the Museo Ernest Hemingway. In the evening savor a cigar and fine añejo (aged) rum on the patio bar at the Hotel Nacional. This elegant setting provides the perfect ambiance to unwind and enjoy the finer things in life, while soaking in the hotel’s historic charm.

Start your second day with a guided visit to a cigar factory—Fábrica de Tabaco H. Upmann is the best. Immerse yourself in the world of Cuban cigars as you witness the intricate process of tobacco cultivation, curing, and rolling. Learn about the different types of cigars and the unique characteristics of each blend. Stock up on your favorite smokes here, taking advantage of the opportunity to purchase authentic Cuban cigars directly from the source. Then spend time around Parque Central, a vibrant hub where you can chat with the owners of dozens of restored classic cars that they rent out to visitors. Admire these automotive masterpieces and learn about their history and restoration. If you want to know how locals travel, hop into a colectivo taxi at the corner of Neptuno and Prado. Experience the city like a true Habanero as you navigate the streets in these shared taxis, which offer a unique glimpse into the local way of life. In the afternoon, visit the Museo de Ron, a museum dedicated to the history and production of Cuban rum. Learn about the different types of rum, the distillation process, and the aging techniques that contribute to their unique flavors. Savor mojitos next door at Bar Dos Hermanos—Hemingway’s favorite dockside bar. Follow in the footsteps of the legendary author and indulge in this refreshing Cuban cocktail, while enjoying the bar’s lively atmosphere and waterfront views. After dinner at La Guarida, head to Tropicana for a sensational ‘50s-style cabaret alfresco. Be mesmerized by the dazzling performances, vibrant costumes, and infectious music that capture the essence of Havana’s golden age.

Before heading back to the airport, visit the Nostalgicar workshop to learn how this private business restores old clunkers. Witness the dedication and craftsmanship that goes into preserving these automotive treasures, and gain a deeper appreciation for Havana’s unique car culture.

#4 Architecture Appreciation

The buildings in Havana come in a spectacular amalgam of styles—from classical colonial mansions to Art Deco, Art Nouveau, and Modernist stunners in various states of repair. This itinerary focuses on the best examples in every genre, providing an immersive exploration of Havana’s architectural diversity.

Upon arrival head to Habana Vieja. The colonial quarter is chock-full of astonishing heritage sites, concentrated around the four main plazas. Immerse yourself in the rich history and architectural splendor of this UNESCO World Heritage Site, as you explore the beautifully preserved buildings and squares. Don’t miss the Hotel Raquel, its jaw-dropping façade dripping with Art Nouveau adornment. Marvel at the intricate details and elegant curves of this architectural masterpiece, which stands as a testament to Havana’s artistic heritage. It’s hard to tear yourself away from the old quarter, but spend the afternoon walking the Prado—a true journey back in time—and end by exploring around Parque Central, taking in the Edificio Bacardi (Cuba’s finest Art Deco exemplar) and the baroque Gran Teatro. At night savor cocktails, and perhaps a cigar, atop the Gran Hotel Manzana Kempinski, with its astounding view of the park and its floodlit architectural stunners. This rooftop bar offers a breathtaking panorama of Havana’s cityscape, allowing you to appreciate the architectural beauty of the city from a unique perspective.

Dedicate day two to Vedado, developed in the 20th century as an upscale neighborhood boasting grandiose mansions. Any stroll here is an architectural adventure in serendipity, but Calle 17 unfurls west past one astounding building after another. Lose yourself in the architectural tapestry of this neighborhood, as you discover hidden gems and marvel at the diverse styles that define its character. Turn right at Paseo for the Hotel Riviera—a superb example of mid-century Modernism courtesy the Mob. This iconic hotel stands as a testament to Havana’s glamorous past, offering a glimpse into the city’s rich history and cultural heritage. Cool off in the late afternoon with ice cream at Coppelia, built in 1966 with flying-saucer inspired architecture. This whimsical ice cream parlor is a beloved institution in Havana, offering a unique architectural experience and a refreshing treat. Dine at La Casa, a paladar in a superb Modernist home in Nuevo Vedado, then end with cocktails and a cigar at the Hotel Nacional, with its Moorish interior.

On day three, head back to José Martí International Airport for your departure flight via 5ta Avenida through the tony Miramar and Cubanacán districts, which display lavish mansions. Don’t miss the outlandish Russian Embassy, an architectural statement that reflects the unique relationship between Cuba and Russia.

#5 Culinary Cuba

“New Cuba” is experiencing a gastronomic revolution led by owner-chefs of the city’s paladar private restaurants. In the morning, head to Habana Vieja, where the area between Cinco Esquinas and Calle O’Reilly—between Parque Central and Plaza de Armas—is an epicenter for these exciting new paladares. These culinary hotspots offer a diverse range of flavors and dining experiences, showcasing the creativity and innovation of Cuba’s new generation of chefs. Lunch at El del Frente on superb ceviche or tuna tataki, washed down with rooftop cocktails. Enjoy the fresh flavors of the sea and the vibrant atmosphere of this rooftop paladar, which offers stunning views of Old Havana. After feeding your soul on the sights, break for a pick-me-up cappuccino at Azúcar, on the Plaza Vieja; it serves delicious lobster in criolla sauce and has live music at night. Or head to nearby Mama Inés, where Fidel’s former private chef conjures up a divine octopus with garlic and pepper appetizer, and the best ropa vieja (marinated braised beef prepared with garlic, onions, and sweet peppers) in town.

The next day experience food like a local. Visit a bodega (ration store), head to a produce market such as Agropecuario Egido, then learn to cook a lo cubano with Niurys Higueras at her paladar Atelier, in Vedado. This hands-on cooking class offers a unique opportunity to learn about Cuban cuisine and cooking techniques, while immersing yourself in the local culture. Mix up your day with some sightseeing. Then, having been sure to make reservations well ahead, take a sunset tour in a classic convertible car that will drop you at restaurant La Guarida—truly a stand-out dining experience!

On day three, head to the nearby community of Alamar for a fascinating guided tour of Organipónico Alamar—Cuba’s preeminent private organic farm—before heading to the airport for your departure flight.