The real and the imagined
Arriving in Cuba is like walking into an elusive myth, a land that seems to shift and change in response to imagination. When Columbus first arrived, he sailed to the southern coast and went back to Spain, convinced that he had reached the mainland. Only when the mariner Sebastian de Ocampo sailed along the southern coast and back north into the mixed waters of the Caribbean and Atlantic was Cuba revealed to be an island. Your stay here will take you back and forth between what the island is and what people think it is, a journey that will teach you as much about yourself as about Cuba.
Day 1: Arrival
After settling in at the Hotel Saratoga, you will head out with David, who will be your guide for the next few days. David is a bright, easygoing, and open companion who will help you savor Cuba’s remarkable heritage, a blend of Latin and African cultures.
You wanted to learn more about Cuba’s famous cigars, so your trip will start with a tour of the Cohiba factory. Founded in 1966 by Celia Sanchez Manduley, Castro’s secretary during the revolution, it is located in an expropriated mansion along Country Club Road. The lovely bones of the house are astonishing, and the surrounding gardens are well maintained. Inside, row upon row of workers sort, smooth and roll tobacco leaves by hand to make four types of cigars, their nimble fingers producing almost 2 million each year. Though the work is labor-intensive, the women smile and laugh easily, their unusual hairstyles, colorful nail polish, and casual clothing breaking the monotony of the scene.
Your day will end with a stylish dinner at El Cocinero, a four-story restaurant with an indoor and outdoor dining terrace and a sleek rooftop snack bar located in the old Cocinero oil factory. After that, I suggest you head to the neighboring Fabrica de Arte Cubano (FAC) for a fun-filled night with Cubans of all kinds. It’s an amazing space that could be in Tribeca—a converted industrial warehouse that serves as a nightclub and outdoor music venue. It also hosts fashion shows, photo exhibits, and contemporary art. Unwind with art, music, and culture in a crowd of chic young Cubans.
Day 2: Art in Cuba
Cuba’s history as a hub for Spanish exploration of the Caribbean made it a crossroads of people, ideas, material, and cultures, creating a rich cultural blend—the perfect incubator for thriving art. In the modern era, communist ideology erased the economic burden of being an artist, leading to a flowering of artistic talents.
Your day will start with a tour of Cuba’s National Museum of Fine Arts led by Luz, a lovely 60-year old lady who used to be the head of the museum. Located in a wonderful midcentury building that calls to mind NYC’s Guggenheim Museum, the National Museum houses the only all-Cuban collection of paintings and sculpture in the world. The collection spans over 100 years, sweeping from early pieces through the Modernist 1970s to provocative contemporary material that engages with current social and political issues.
Before lunch, you will take a short drive along Country Club Road to see more of the houses, fabulous remnants of a lost era. Lunch will be in one of Havana’s small, family-owned restaurants—known as apaladares—where you can enjoy delicious local cuisine. I suggest trying pork with tamales and nuggets of lobster, all washed down with a mild mojito.
Next, a visit to the Ludwig Foundation, a non-profit located in a beautifully restored penthouse that supports young contemporary artists. You will get an overview of their work by Alvaro, a Cuban involved with the foundation whose knowledge and passion for art are infectious. From there, you will go to Clandestino: Tienda de Diseno, a tiny shop that sells quirky t-shirts and bags, tucked away in a corner of old city.
Dinner will be at La Cocina de Lilliam, another family-run restaurant and a culinary gem. The owner, Lilliam, runs the kitchen with her daughter and brother and is always happy to greet guests. Be sure to try the delicious plantain chips and the grilled shrimp appetizer—which comes with a goldfish swimming in a bowl!
Day 3: Light and dark in the city
An early morning walk will give you a chance to enjoy Havana by dark. You will notice that most of the streets have little or no lighting, and very little light comes from the buildings. Enjoy the indrawn breath of this unique capital, the feeling of expansive emptiness and quiet, as though you’re walking past the uninhabited buildings of a forgotten city. As the city wakes up, wander through the crumbling, rambling streets of the old town, with bicycle rickshaws and classic car taxis weaving between scantily clad pedestrians, and feel the press of people as the day begins.
After the morning walk, you will travel to Castillo del Morro, a fort across the channel. From the lighthouse, you can look back at the city across the Havana channel. Visiting the highest point in a place not only gives you a sense of where you are but also of the larger patterns that shape the lives of the people there.
In the afternoon, you will visit the house of the artist Kodir Lopes-Nieves, who collects old industrial and business signs and paints social commentary on them—for example, he collaged a photo of 1950s gamblers around a casino table over a Wells Fargo sign. Lopes-Nieves has also revived the art of neon and possesses the only neon light maker in Cuba, which he uses to replace business signs on abandoned business buildings throughout the city. You can spend some time discussing Cuba’s art and history with him, getting to know the twins, pain and beauty, that have forged the soul of this island, his home.
Day 4: From the fifties to today
Per your request, you will visit Finca Vigia, the house Hemingway shared with Martha Gelhorn. This is where he wrote The Old Man and the Sea, and his boat, the Pilar, is still here, along with his books, typewriter, mounted animal heads, and Spanish bullfight posters—everything just as it was when he was in residence.
Before lunch, make a quick stop at the Hotel Nacional for a class in Mojito making and a chance to see this massive, venerable building. Lunch will be at a paladar called HM7, a restaurant offering an ocean view and an open kitchen, so you can see the cooking—the chef even wraps up the course at your table. I think you will like the lobster and octopus, but there’s also plenty to choose from on their multicultural menu.
Once satiated, head back to the hotel, where Fidel Castro’s deputy minister of foreign affairs, José Viera Raul Linares, will give a talk on Cuba-US relations from the ’50s to today. Linares is a charming man of great erudition, and his wife, Cecilia, is knowledgeable and wise. Meeting such people is what travel is all about, a transformative experience that creates a link between two worlds, two realities.
End the day with a jaunt in a classic car—a fabulous bubblegum-pink ’56 Chevy convertible with a catcall horn. Speed down the Malecón in this glorious old automobile, waves crashing over the wall as the sun sets in the distance.
Day 5: Old Havana
Start the day with a walking tour of Old Havana, a picturesque old town with wide, cobbled streets and extravagant houses. Most of the houses were built by Cuba’s wealthy during the island’s sugar boom, the ‘Fat Cow’ period after the First World War. The island was flush with cash, and the people lavished it on glorious houses built in the European style. You can amble along and enjoy the facades, pop into renovated courtyards, and pause for coffee in the old squares.
After a short rest at the Saratoga, out again for drinks at the studio of Esterio Segura, Cuba’s best-known contemporary artist. Segura, who looks almost Hawaiian, with a wide face, braided pigtails, a ready smile and bright eyes, produces work that is highly critical of Castro and the government’s policies; he’s a protest artist who delicately balances commentary and aesthetics. Despite his success, he remains a gentle, insightful man, comfortable in his own skin. I’m sure the two of you will have a memorable discussion.
Dinner will be at Ivan Chef Justo, famous for its succulent suckling pig.
Days 6 – 7: Beyond Havana
You will spend these two days traveling outside Havana, taking in the island’s remarkable beauty, culture, and history. The journey starts with a trip to Viñales, a wonderful karst landscape that has been incorporated into a national park. You will hike through this lush valley and have a chance to explore the caves or go horseback riding. At the bottom of the valley, you will visit the farm of a smallholding tobacco farmer, a cross between John Wayne and the Marlboro Man. Take the chance to run your fingers over a tobacco leaf—the sensation is surprisingly sensual!
From Viñales, you will head to Cuba’s pristine Puna Frances Marine National Park on Isla de la Jeventud, home to a spectacular reef and miles of white sand that never see a footprint. After a few hours scouting the area by boat, you will head back and cross to the island’s north, driving past horse carts and vintage trucks on a highway ribboning through rural countryside on the way to Cayo Santa Maria, one of 3000 islands strung out along the north coast. Cayo Santa Maria is connected to the mainland by a long causeway. Though it has an international airport for Canadian and European tourists, the area is still only lightly developed.
The next day, you will head back to explore Matanzas and Varadero, halfway between Santa Maria and Havana. At Matanzas, you will visit the Ermita de Monserrate, a church with a stunning view of the city and the bay, where there will be a concert by the Catalonian Chorus, a group of 16 youths who travel throughout Cuba and abroad, sharing their eclectic repertoire of music.
Back in Havana, you will visit the Museum of Ceramics, located in a wonderful house in the old city, which was built in 1840. Its two floors house a range of ceramics in gracious rooms surrounding an arched courtyard where classical guitar maestros often play. As darkness falls, savor the museum’s quiet glow, close your eyes and let the music envelop you.
Day 8: So close and yet so far
Travelling is as much a journey of the imagination as a journey through the world. Expectations are at the heart of every journey, but no expectations can anticipate what it feels like to travel through Cuba, a rich, nuanced country where every encounter is refracted through the prism of your life and your preconceptions. Every journey is shaped by your interior landscape, but few other places find travelers so unprepared for the reality that greets them. In the spirit of this sort of interpretive interaction with reality, you will wrap up your trip with a visit to the National Theatre of Cuba. There, you will have a chance to attend the morning class of the Contemporary Dance Troop. The energetic instructor leads 25 dancers through a session that starts with head rolls and progresses slowly through an array of movements, blending yoga with African dance. As the exercises pick up speed, bodies leap into the air, spinning and dropping onto the floor. When the music begins—congas, rattles, and singing—you will see the room erupt with spirit, filling with laughter as the dancers rumba, sway, stomp and howl. What a perfect note to end the trip on!
And that, Serge, is Cuba, an unusual island full of music, art, food, and culture, a blend to tempt any palate. It was a great pleasure to give you a taste of this extraordinary place. Keep exploring, and please give me a call if I can be of service.