Call us: (910) 742-5324
Call us: (910) 742-5324
Join Sisterhood Travels for an unforgettable, women-only cultural immersion in Havana, Cuba, crafted specifically for American women who want to experience Cuba legally, authentically, and meaningfully. This intimate journey offers a rare opportunity to connect directly with Cuban artists, dancers, historians, entrepreneurs, and families—giving you access to the real stories behind the headlines.
You’ll explore the vibrant streets of Old Havana, ride in classic 1950s American cars, dine in family-run paladares, and engage in exclusive cultural experiences that most travelers never get to see. From hands-on cooking lessons to powerful conversations with community leaders and local women, this is more than a tour—it’s an invitation into everyday Cuban life.
The only way to truly understand Cuba, its beauty, complexity, and resilience, is to meet her people. No filters. No headlines. Just heart-to-heart connection. You’ll witness the resilience, humor, and heart of the Cuban people—something no amount of outside commentary or propaganda can truly convey.
This is legal travel to Cuba under the In Support of the Cuban People license, designed to comply fully with U.S. travel restrictions—while offering you a deeper, richer, and more truthful perspective on Cuban culture.
Reserve your spot now—space is extremely limited.
Architecture, culture and history come together in this unique hotel located in Old Havana and designed for the most curious travellers to enjoy a fantastic urban experience. Surrender to the charms of a city that vibrates day and night, and discover with INNSiDE the most emblematic corners of the capital of Cuba.
Welcome to Havana! Upon arrival at the Havana airport, proceed through Cuban Immigration where your carry-on bags will be scanned. Collect your checked bags and go through Customs. Our representative will meet you after Customs and transfer you to our beautiful hotel where you’ll have free time to settle in and get oriented. This evening, we’ll begin our adventure with Tapas & Talk, an elegant Welcome Dinner featuring a self-serve tapas buffet at the rooftop pool of our hotel, overlooking the Bay of Havana. This will be your opportunity to meet your Group Leader and new Sisters. We’ll also meet our Tour Director who will provide us with a tour briefing and orientation. (Dinner included)
After breakfast, we’ll embark on a morning stroll in Old Habana as we visit each of the four colonial plazas: Plaza de San Francisco, Plaza de Armas, Plaza Vieja, and Cathedral Square. Each is full of color and personality, with a mix of palatial buildings, monuments, museums, galleries, churches, lively entertainment, restaurants and bars. Attending Sunday mass at the Cathedral of Havana is a unique experience and offered in Spanish: you are welcome to attend all or parts of the service. Those who choose not to attend, can return to the hotel which is only one block away.
Next, we’ll be joining Cuban families for a pizza lunch to talk about day-to-day life in Havana. Caring for children, schooling, grocery shopping, and elder care are all open for discussion.
After free time at our hotel this afternoon, we’ll enjoy a delightful rooftop dinner at Atelier, a private restaurant set in a charming home built in 1928. When President Barack and Michelle Obama visited Cuba, the First Lady hosted a lunch at the paladar for Cuban businesswomen. (Breakfast, Lunch, and Dinner included)
This morning, we’ll take a road trip in 1950’s Vintage American cars, a nostalgic experience. We’ll cruise the Malecon, El Bosque, Revolution Square and stop for photos.
Next, we’ll stop at a premium cigar shop in the Castle of the Three Magi Kings of El Morro, near the lighthouse which was built in 1845. This official shop has a broad selection of cigars, rum, and coffee. After, we’ll head for our lunch at El Rum Rum de la Habana, a private restaurant with wonderful seafood in the heart of Old Habana where we’ll be treated to live music and a welcoming staff, with an exclusive opportunity to chat with the musicians after lunch.
Later, we’ll visit the Galeria Raul Corrales, which displays the photography works of Raul Corrales, Fidel Castro’s official photographer from 1959 to 1961. Our private gallery visit will be hosted by Claudia Corrales, his granddaughter. An accomplished photographer in her own right, Claudia serves as a resource person for National Geographic Photographic Expeditions in Cuba. Gallery Limited Edition prints of Raul Corrales’ works are available and come with the Gallery Stamp and a Certificate of Authenticity. Also, available are works by contemporary Cuban photographers.
Next, we’ll offer an optional drop-in at the Floridita, perhaps the most famous bar in Cuba. It’s the cradle of the Daquiri and homage to Nobel Prize winner, Ernest Hemingway. Tonight, we’ll dine together in Havana’s sophisticated Miramar neighborhood at Toros & Tapas, a celebrated Spanish paladar known for its exquisite cochinillo (sucking pig). The menu showcases a fusion of Spanish, Caribbean, and Mediterranean flavors with options to suit vegetarian diners. (Breakfast, Lunch, and Dinner included)
Ballet holds an esteemed place in Cuban culture, with the country acclaimed for producing some of the world’s most outstanding dancers. Founded in 1948 by the legendary Alicia Alonso, the Cuban National Ballet stands as a global symbol of excellence, celebrated for its rigorous training and distinctive artistry. This morning, we will spend time at one of Cuba’s top ballet schools, where we’ll observe the intensive training that shapes these future stars. Following the session, we’ll have the rare opportunity to engage in a conversation with students, gaining insight into their passion for ballet and their aspirations in the world of dance.
Prepare to be amazed when we head to Santy Pescador, one of the best paladars for seafood in Cuba. The distinctive Japanese-Caribbean fusion sets this private restaurant apart, and the sushi is a must. After, you’ll have the opportunity to shop for souvenirs at the Old San Jose Warehouses, a large craft market in an old maritime warehouse by the Bay. You’ll have some down-time before we head to dinner at the unsigned Café Laurent, a sophisticated fine-dining restaurant encased, incongruously, in a glaringly ugly 1950s apartment block. Starched white tablecloths, polished glasses and lacy drapes furnish the bright modernist interior where we’ll enjoy excellent Cuban-Spanish-Mediterranean fusion, with the specialty being dishes of the sea.
After dinner, we’ll head to one of the best jazz clubs in Havana. The La Zorra y El Cuervo (the Fox & Raven) is small and intimate, and you’ll enter this underground club through a British telephone booth. You won’t want to miss this celebration of the jazz that pulses through the veins of Cuba. (Breakfast, Lunch, and Dinner included)
This morning after breakfast, we’ll enjoy a fascinating presentation by Professor Carlos Alzugaray, former Cuban Ambassador to the European Union on U.S.-Cuban relations. He’ll provide an insightful analysis, tracing the relationship from the Cuban Revolution to today’s political landscape.
Next, we’ll visit the Museum of the Revolution where we’ll visit the exterior exhibits before heading to lunch at Ivan Chefs Justo, a private restaurant with wonderful décor and ambiance. Chef Ivan studied in Montréal and was once Fidel Castro’s chef. This afternoon is yours at leisure to relax and enjoy with your Sisters – perhaps at the rooftop pool?
Tonight, we’ll dine together at La Cocina de Liliam, a charming paladar boasting an impressive selection of international cuisines. Over the years, it has welcomed notable figures, including former U.S. President Jimmy Carter during his visit in 2002. (Breakfast, Lunch, and Dinner included)
This morning after breakfast, we’ll make our way to the iconic Hotel Nacional de Cuba, the site of the infamous Havana Conference in 1946, where U.S. mob mastermind Meyer Lansky and legendary crime boss Lucky Luciano gathered top Mafia figures to discuss their business interests. This pivotal meeting, later depicted in The Godfather Part II, shaped the operations of organized crime in the U.S. for decades.
We’ll meet with Dr. Marta Nunez, a Cuban sociologist and retired professor at the University of Havana, on Empowering Women in Cuba: the progress, challenges, and opportunities. Before lunch, we’ll have the opportunity to socialize with the Professor at a private outdoor bar, offering fresh fruit juice and Cuban coffee. We’ve also invited a female attorney, doctor, athlete and Cuban “notorio” who will join us for extended conversations at a specially curated tropical lunch in the picturesque gardens of Hotel Nacional at La Barraca.
This evening, you’re in for a treat! First, we’ll dine together at the paladar Vistamar, on the sea. The wonderful food and airy atmosphere make for a special evening overlooking the infinity pool to the ocean. After, we’ll head to The Tropicana, a Cuban international icon, where we’ll enjoy a glimpse of pre-revolution Cuba, where Carmen Miranda, Josephine Baker, Nat King Cole, and others dazzled wealthy guests with Latin dance numbers and women with 10-pound headdresses performed. (Breakfast, Lunch, and Dinner included)
Today, we’ll escape to a hidden gem 25 minutes east of Havana, where island bliss and tranquility await us. Our exclusive Sisterhood retreat day on the Atlantic Ocean is at the beautifully restored 1950s Tribe Caribe Beach House where our oasis allows us to sink into the soft sands and soul-soothing Tara Beach. Our private beach house features a private courtyard where you can relax while waiting for our private chef and his team prepare our fresh-grilled lobster, chicken, and vegetable lunch. Later in the afternoon, a charcuterie board and fresh tropical fruit will be served as private musicians entertain us. Our air-conditioned beach house will offer unlimited bar service, including soda, wine, rum drinks, beer, and bottled water. To top it all off, you’ll be able to pre-book a relaxing massage – and yes, you can enjoy it on the beach if you’d like. (Breakfast and Lunch included)
This morning, we’ll meet with historian, Gladys Rodriguez, museologist, guardian of Cuba’s artistic heritage, and a renowned Hemingway scholar focused on his enduring legacy in Cuba. Next, we’ll enjoy lunch together at Divino, a farm to table family-run paladar. The proceeds from our meal helps support social programs for the elderly and children in the community.
After lunch, we’ll visit Finca Vigia, Ernest Hemingway’s home and farm, where he accepted the Nobel Prize for Literature and wrote portions of A Moveable Feast, For Whom the Bell Tolls, Islands in the Stream, and much of The Old Man and The Sea.
Next, we’ll visit Proyectongo, a community project focused on art education and opportunities for children. The project is supported by the sale of art by local artists, not the children. It is an excellent place to donate art and school supplies.
Further out of Havana you will have an ‘under the hood’ experience by visiting the workshop of a family-owned and operated business dedicated to the restoration of 1950’s American classic cars. You will meet Julio, the owner, and enjoy his stories. In addition, you will have the opportunity to engage with the mechanics and pose behind the wheel with the likes of Lola (a pink 1956 Chevrolet Bel Air), Nadine (a blue 1955 Chevrolet Bel Air), or Benny (a black 1959 Chevrolet Impala convertible). Tonight is yours for independent dining with your Sisters. (Breakfast and Lunch included)
Today, we’ll travel a short distance to Cojimar, a charming fishing village east of Havana. We’ll make a stop at the water’s edge where Hemingway’s legendary boat, Pilar, was once moored and where a metal bust of Hemingway stands against the backdrop of the 17th-century Spanish Lookout Fort.
Next, we’ll explore the charming organic garden tended to by brothers Jesus and Julio. Here, they unveil the art of cultivating herbs, vegetables, and fruits, most destined for the private restaurant you will soon be and to the local senior center. Notably, herbal medicine is widely used in Cuba, both as a traditional practice and as an integral part of the country’s healthcare system. Due to shortages of conventional medicines, many Cubans turn to natural remedies derived from plants, herbs, and roots. You will have the opportunity to discuss with ‘abuela’ (grandmother) her personal use of organic herbs and plants for medicine for her family.
In this picturesque fishing village, just a few blocks from the bay, we will go to the paladar El Ajiaco. The private restaurant wears its humble charm with pride, a place where flavors matter more than frills. Food networks from around the world have visited its unassuming warmth, and notable celebrities like Kevin Bacon and Sigourney Weaver have stepped through the doors.
Our cooking and mojito-making lessons takes center stage. You will work side by side with humorous and talented Cuban chefs, shaping multiple dishes that celebrate the island’s flavors: Lobster, succulent and brimming with ocean essence, Ropa Vieja, the tender shredded beef stewed in aromatic spices, and Ajiaco soup, a hearty blend of root vegetables and herbs. But there’s more—the barkeep beckons. You will craft yourself a special Cuban mojito, balancing mint, lime, honey, and rum. Savor the moment. Roll up your sleeves, stir the pots, and raise your glass. This experience isn’t just about food; it’s about connecting with Cuba’s soul, one delicious bite at a time.
Enroute back to Havana, we’ll pause to take in the breathtaking panoramic view of Havana and the bay, where we’ll stop for photos at the Christ of Havana, a colossal statue with a tale of its own. The rest of the afternoon and evening is yours to enjoy with your Sisters. It’s our last evening in Cuba – Disfruta de la noche (enjoy the night)! (Breakfast and Lunch included)
After breakfast, we’ll transfer to the Havana airport for our departures home, carrying with us unforgettable memories of our wonderful adventure together in the Pearl of the Antilles, and of course, each other. (Breakfast included)
PLEASE READ THIS INFORMATION CAREFULLY
This immersive cultural journey through Havana and its surrounding gems is perfect for women who are comfortable walking and standing for moderate periods and engaging in full days of scheduled activities. In accordance with U.S. travel regulations for “In Support of the Cuban People”, participation in all itinerary experiences is mandatory. This enriching experience blends walking tours, educational site visits, meaningful conversations with locals, music, art, and cuisine, with plenty of opportunities for cultural connection and reflection.
Walking & Standing
Expect moderate walking most days, often on cobblestone streets, uneven sidewalks, or within historical buildings and outdoor plazas. Daily sightseeing includes guided walking tours through Old Havana’s colonial plazas, gallery and museum visits, market browsing, and cultural interactions that may require standing for extended periods. Some venues have stairs or minimal seating. Optional activities such as visiting the Floridita bar or dancing at jazz clubs require additional walking or standing but are not physically strenuous.
Terrain, Transport & Accommodations
While Havana is relatively flat, many streets are worn, uneven, or cobbled, and curb heights can vary. Most walking will be done at a leisurely pace. All transportation is provided, including air-conditioned coaches and vintage American cars. Hotels are comfortable, centrally located, and equipped with elevators, though some boutique venues or restaurants may require climbing short flights of stairs. Some days include longer durations on foot, with breaks throughout the day to rest or return to the hotel.
Cultural Experiences & Required Participation
Under U.S. government licensing for legal travel to Cuba, participation in all group activities is required and non-optional. The itinerary includes visits to artists, academics, entrepreneurs, and community leaders, hands-on cultural activities (such as cooking classes and dance or music engagements), and talks with experts in Cuban society. Every day is designed to deepen your understanding of Cuba’s vibrant culture, history, and people. While not physically strenuous, these experiences require an open mind, attentiveness, and full-day engagement.
Pacing & Free Time
This itinerary is full but thoughtfully balanced, with blocks of free time built in for rest or personal exploration. Days typically begin around 8:00–9:00 a.m. and conclude after dinner or late-evening entertainment. While there is time to recharge at the hotel or rooftop pool, please be prepared for sustained engagement throughout the trip to meet the legal requirements of your visa.
