Call us: (910) 742-5324
Call us: (910) 742-5324
Viva Cuba: Walk Through History, Feel the Soul. Step into a world few travelers ever truly see on Sisterhood Travels’ exclusive women-only tour of Cuba: an immersive, emotionally rich journey through the heart of the Cuban Revolution and the soul of modern Havana. This intimate experience is limited to just 12 Sisters, offering you an extraordinary opportunity to connect deeply with the island’s revolutionary past, vibrant culture, and with one another.
From Santa Clara to Trinidad and Havana, you’ll explore the exact locations where history was made, from Che Guevara’s final resting place to the site of the pivotal Bay of Pigs invasion. You’ll stand where Fidel Castro claimed victory, where Ernest Hemingway found his muse, and where everyday Cubans continue to preserve the spirit of their revolution with pride and purpose.
This itinerary isn’t just sightseeing—it’s a once-in-a-lifetime cultural experience, designed to meet U.S. legal travel guidelines under the “Support for the Cuban People” license. Every moment is meaningful: whether you’re listening to a retired Cuban ambassador unpack decades of U.S.–Cuba diplomacy, sharing farm-to-table meals with local families, or dancing under the stars in a centuries-old plaza.
Sisterhood Travels has intentionally limited this tour to just 12 women to ensure a slower, more thoughtful pace, allowing for real conversations with Cuban scholars and everyday citizens. You’ll not only explore Cuba: you’ll feel it, through music, through memory, and through the magic of shared experience. This is community. Sisterhood. Transformation.
This is more than a tour. It’s a rare chance to walk in the footsteps of revolutionaries, to sit in Hemingway’s writing room, to feel the resilience in every conversation, and to leave not just informed, but transformed. Spaces are extremely limited, and they will fill quickly. If you’ve ever dreamed of seeing Cuba beyond the guidebooks, this is your moment. Join Sisterhood Travels in November 2026 for an unforgettable, all-women journey through Cuba’s revolutionary past and its dynamic, colorful present.
Your Cuban adventure begins as you touch down in Santa Clara—an unfiltered, vibrant city steeped in revolutionary history. After clearing immigration and customs, you’ll be greeted by our warm and welcoming Cuban representative. From there, it’s a private ride into the heart of the Old City, where your hotel sits right on the edge of charming Leoncio Vidal Park. Take a moment to settle in, stretch your legs, and soak up the colonial architecture that surrounds you. This evening, get your first taste of Cuba at FUSIONe, a chic local paladar known for bold culinary creativity and friendly vibes. It’s the perfect way to kick off your journey! (Dinner included)
Hotel: Hotel Central Santa Clara
Today, we dive deep into the legacy of one of the most iconic and controversial figures of the 20th century: Che Guevara. You’ll begin the morning with a fascinating briefing that unpacks the life, ideology, and impact of this revolutionary legend. Then, we’ll head out to explore Santa Clara, a city forever tied to Che’s story.
After a relaxing farm-to-table lunch in the countryside, you’ll visit the Monument to the Armored Train, where Che and a small band of guerrillas pulled off a bold and pivotal victory that helped seal the fate of Batista’s regime. Then, stand in awe at the Che Guevara Mausoleum, a powerful memorial and museum honoring his life and legacy. The towering bronze statue, his final resting place, and the stories within the museum offer a poignant look at the man behind the myth.
This is a day rich in revolutionary history and emotional resonance – one you won’t soon forget. This evening is yours to dine and explore independently with your Sisters. (Breakfast and Lunch included)
Hotel: Hotel Central Santa Clara
Today, you’ll trade the revolutionary streets of Santa Clara for the stunning mountain roads of the Escambray range. As we wind through the lush highlands of Topes de Collantes, soak up breathtaking views and fresh mountain air, a scenic escape that feels like stepping into another world. A peaceful, rustic lunch in the heart of the forest gives you time to take it all in before heading toward the southern coast.
By afternoon, we’ll arrive in Trinidad, an absolute gem of a city and a UNESCO World Heritage Site. With its cobblestone streets, pastel-hued colonial homes, and timeless charm, this town feels like it’s frozen in history. Spend some free time with your Sisters wandering its romantic streets and plazas, camera in hand and curiosity wide open.
Dinner tonight is at Taberna La Botija, a lively spot where food, music, and revolutionary history come together. Sip a traditional canchánchara, the beloved local cocktail invented by guerrilla fighters right here in Trinidad. Served in clay cups and steeped in legend, it’s the perfect toast to Cuba’s resilient spirit.
As the night falls, join the locals on the iconic steps near Plaza Mayor for live music under the stars, an unforgettable slice of Cuban nightlife where dancing, laughter, and rhythm fill the air. (Breakfast, Lunch, and Dinner included)
Hotel: Iberostar Grand Trinidad
Our day begins with a gentle, guided stroll through the heart of Trinidad. As you wander its cobbled lanes and sun-drenched plazas, you’ll uncover the stories that shaped this colonial treasure, one pastel-colored building at a time. From its 16th-century roots to its golden age as a sugar trade hub, every corner holds a piece of Cuba’s layered past.
In the afternoon, you’ll step back even further in time with a visit to the Valle de los Ingenios, the once-thriving Valley of the Sugar Mills. This lush landscape was the beating heart of Cuba’s sugar empire in the 18th and 19th centuries. You’ll visit haunting landmarks like the towering Iznaga Tower, used to oversee enslaved workers, and the crumbling stone quarters where they once lived. It’s a powerful, sobering glimpse into the realities behind the region’s colonial wealth.
This evening, we’ll return to the serenity of Trinidad and to enjoy a memorable dinner at Casa Museo 1514. Set inside a stunningly preserved colonial mansion, this unique paladar surrounds you with antiques and ambiance as you dine. It’s the perfect blend of history, elegance, and Cuban hospitality to wrap up your day. (Breakfast and Dinner included)
Hotel: Iberostar Grand Trinidad
This morning, we’ll journey westward toward one of Cuba’s most storied shores, Playa Girón on the Bay of Pigs. As we travel across the Zapata Peninsula, roadside memorials honor the Cuban soldiers who defended their homeland during the dramatic 1961 invasion. At the Bay of Pigs Museum, you’ll dive into the gripping story of how a CIA-backed mission unraveled on these very beaches, forever changing Cuba’s place on the global stage.
Afterward, enjoy a peaceful stop at El Guajira, a family-run farm where tropical fruit trees flourish and fresh juice flows. If you’re lucky, you might even sip a smoothie made from the elusive mamey fruit, an island favorite. Time permitting, there’s also an optional visit to the small town of Australia, where Fidel Castro once led his counteroffensive from a sugar mill that now serves as a modest but moving museum.
Then it’s on to Havana, a city that defies definition and dances to its own rhythm. With its fading grandeur, fierce pride, and streets that pulse with music and memory, Havana seduces without trying. After checking in at our centrally located hotel, we’ll head to Plaza Vieja, a lively square once home to Havana’s aristocracy and now a hub for music, dining, and local life. Spend the evening at your own pace with your Sisters, exploring Havana’s café culture, chatting with locals, or just soaking in the sultry air of a city that’s survived, and thrived, against all odds. (Breakfast included)
Hotel: Iberostar Selection Parque Central Havana
This morning, you’ll step into the halls of Havana’s grand dame, the legendary Hotel Nacional. With sweeping views over the Malecón and a guestbook that once read like a who’s-who of Hollywood and organized crime, the Nacional has seen it all. From the infamous 1946 Mafia summit to Cold War tensions during the Cuban Missile Crisis, this storied hotel has quietly witnessed some of the 20th century’s most dramatic moments.
Next, you’ll take a front-row seat for a riveting talk by Professor Carlos Alzugaray, a former Cuban ambassador and expert on U.S.–Cuba relations. His insight weaves together decades of diplomacy, conflict, and cultural connection, offering a rare chance to understand this complex relationship from the inside out.
Our historical journey continues at the Hotel Habana Libre, once the glamorous Habana Hilton. Here, you’ll step inside Suite 2324, where Fidel Castro and his revolutionaries set up headquarters just days after toppling Batista. It’s a surreal contrast between revolutionary grit and Hilton-era glamour, and a powerful reminder of how Cuba redefined itself room by room.
After a cozy lunch at 5 Esquinas Trattoria, tucked away in Old Havana, you’ll visit the Museum of the Revolution to view its striking exterior exhibits, including the famous Granma yacht, which carried Fidel, Che, and 80 others on their daring 1956 mission to spark rebellion.
Then it’s on to El Capitolio, Havana’s awe-inspiring national Capitol building. Recently restored to its full glory, this architectural gem is once again home to the Cuban National Assembly, symbolizing both Cuba’s storied past and evolving present.
This evening, you’ll be treated to an elegant dinner at Fangio Habana, nestled in a beautifully restored mansion along Paseo Avenue. Fusing Mediterranean flair with Southeast Asian influences, the chef’s creations reflect Havana’s rich, cross-cultural soul. Every bite is a love letter to Cuba’s bounty: fresh, bold, and unforgettable. (Breakfast, Lunch, and Dinner included).
Hotel: Iberostar Selection Parque Central Havana
Today, we’ll start our morning in the company of one of Cuba’s most respected cultural voices: historian and Hemingway scholar Gladys Rodríguez. With warmth and wisdom, she’ll share stories of Hemingway’s deep connection to Cuba: the landscapes that inspired him, the characters he met, and the quiet strength he found here during two of his most prolific decades.
Afterward, we’ll journey to Finca Vigía, Hemingway’s beloved hilltop retreat just outside Havana. It’s where he wrote The Old Man and the Sea, accepted his Nobel Prize, and hunted marlin aboard his boat Pilar, still resting on the grounds. As you explore the rooms frozen in time, you’ll see Papa’s handwritten notes, well-worn typewriter, and the view that stirred some of his greatest prose. It’s a rare, intimate look at the writer behind the legend.
For lunch, we’ll head to Divino, a charming farm-to-table oasis nestled in the peaceful countryside. With food grown on-site and a mission that supports the local community, this family-run paladar serves up more than just a delicious meal: it offers a glimpse into Cuban resilience, creativity, and heart.
This evening, prepare to be swept off your feet. You’ll dine seaside at Paladar Vistamar in Havana’s chic Miramar neighborhood, where the waves kiss the terrace and an infinity pool blends seamlessly with the sea. With fresh seafood, fine wine, and Caribbean breezes, it’s an elegant farewell to Cuba’s culinary delights.
But the night isn’t over yet. Your grand finale? An unforgettable evening at Tropicana, Havana’s legendary open-air cabaret. Beneath the stars and amidst the palms, more than 200 dancers, singers, and acrobats dazzle in a whirlwind of rhythm, feathers, and flair. It’s old Havana glamour at its finest, where the spirit of Carmen Miranda and Nat King Cole lives on in every beat. So put on your casual elegance, sip your mojito, and let the magic carry you away. (Breakfast, Lunch, and Dinner included)
Hotel: Iberostar Selection Parque Central Havana
Our final day in Cuba begins in true Havana style: cruising through the city’s iconic streets in a classic 1950s American car. With the wind in your hair and the sea by your side, you’ll glide along the Malecón, Havana’s famed seaside boulevard, where pastel buildings, ocean spray, and vintage chrome create a picture-perfect farewell to the golden age of Cuban glamour.
Then, we’ll step into the present, and reflect on the past, with a visit to the Centro Fidel Castro Ruz. This sleek, modern museum offers a nuanced look at the life, philosophy, and legacy of Cuba’s most influential revolutionary. Through immersive exhibits and personal artifacts, you’ll explore Fidel’s complex role in shaping modern Cuba, both celebrated and contested. It’s a space that encourages thoughtful reflection and invites you to grapple with the weight of history, just as Cubans continue to do today.
To celebrate our journey, we’ll gather for a farewell lunch at Boutique Casa Italia, a refined hideaway tucked inside a beautifully restored 1920s mansion in Miramar. Surrounded by flowering gardens and timeless elegance, you’ll savor handmade pastas, fresh seafood, and a final glass of wine under the Cuban sun. It’s the perfect pause to relive the memories, friendships, and insights gathered along the way.
The afternoon is yours to enjoy however you choose with your Sisters. Perhaps you’ll take that one last wander through Old Havana, a quiet hour on the hotel’s rooftop, or a final stop at that favorite café where the music never stops. Dinner tonight is on your own, so feel free to let the rhythm of Havana guide you to one last delicious discovery. Whether you dance the night away or sip a quiet cocktail under the stars, this evening is your time to say goodbye in your own unforgettable way. Disfruta de la noche. Enjoy the night, and the memories you’ve made in a place unlike any other. (Breakfast and Lunch included)
Hotel: Iberostar Selection Parque Central Havana
After one last breakfast in Havana, it’s time to say farewell to this vibrant island that has shared so much history, heart, and soul with us. As we head to the airport for our flights home, we’ll carry with us the rhythm of the music, the warmth of the people, and the powerful stories that brought Cuba’s past and present to life.
More than just a destination, Cuba has been a journey: through revolutions, culture, cuisine, and connection. And while we may be leaving the Pearl of the Antilles, we take with us something even more lasting: the friendships we’ve made and the memories we’ll never forget.
Until next time—hasta luego, amigas. (Breakfast included)
PLEASE READ THIS INFORMATION CAREFULLY
ACTIVITY LEVEL: 3 – Moderate
This immersive cultural journey through Santa Clara, Trinidad, Havana, and historically significant sites like Playa Girón and Finca Vigía is ideal for women who are comfortable walking and standing for moderate periods and engaging in full days of enriching, scheduled activities. This thoughtfully curated experience blends walking tours, historical explorations, cultural conversations, music, cuisine, and reflection across multiple regions of Cuba.
Walking & Standing
Expect moderate walking on most days, often on cobblestone streets, uneven sidewalks, mountain roads, or within historic buildings, museums, and open-air sites. Guided walking tours will take place through Old Havana, colonial Trinidad, and significant revolutionary sites including Che Guevara’s mausoleum and the Bay of Pigs Museum. You’ll also explore gardens, memorials, and outdoor plazas that may require standing for extended periods. Seating may be limited at some cultural venues, and stairs may be present at heritage properties, restaurants, and museums.
Terrain, Transport & Accommodations
This itinerary includes a variety of terrain from the lush mountain roads of the Escambray range to the narrow, often uneven streets of Cuba’s colonial cities. While most walking is done at a relaxed pace, some rural and historical sites require light walking on gravel paths or through modest inclines. Long-distance transportation is provided by air-conditioned motorcoach, while short rides include vintage American cars. Hotels are comfortable, centrally located, and typically offer elevator access. However, some paladares and museums may involve climbing stairs or short uphill walks.
Cultural Experiences & Required Participation
In accordance with U.S. travel licensing regulations, participation in all scheduled group activities is required and non-optional. These experiences include educational briefings, visits to revolution-era landmarks, guided museum tours, interactions with artists and experts, music and dance performances, and time spent in rural communities. While not physically strenuous, these activities do require curiosity, attentiveness, and full-day engagement. Scheduled events may occur in warm weather or in open-air environments with minimal climate control.
Pacing & Free Time
This itinerary is full and immersive, with daily schedules typically beginning between 8:00–9:00 a.m. and extending into the evening, especially on days that include music or entertainment. Blocks of free time are included for personal rest, relaxation, or independent exploration. Please be prepared for sustained cultural and educational engagement throughout the trip in order to meet the legal requirements of your visa.
