HAVANA JAZZFEST
January 24 – February 1, 2027
Havana JazzFest 2027
A Once-in-a-Lifetime Women’s Journey to the Heart of Cuba
Limited to 8 Women | Single Occupancy | Boutique Hotel Exclusively for The Sisterhood
Get ready to soak up the soul of Havana during one of the most electrifying cultural events in the Caribbean: the Havana Jazz Festival 2027! This is not just a trip! It’s a transformative women-only travel experience designed for those who crave rhythm, sisterhood, and the magic of Cuba’s timeless charm. Over 9 unforgettable days, you’ll explore Havana’s cobblestone streets, vibrant art scene, and rich cultural history, all while enjoying VIP access to world-class jazz performances featuring legendary Cuban and international artists.
What makes this journey truly extraordinary? Our private, boutique hotel, exclusively reserved for our Sisterhood, is nestled in the elegant Vedado district, offering both tranquility and style just steps from the city’s heartbeat. With only 8 spots available (yes, just 8!), each woman enjoys her own room, allowing for comfort, connection, and a true sense of retreat. From hands-on mojito and cooking classes to rooftop dinners, classic car rides, private art tours, and curated local encounters, every detail has been crafted for immersion, ease, and unforgettable memories.
Join us as we celebrate culture, music, and Sisterhood in one of the most captivating cities on earth. Spaces are extremely limited—reserve yours before it’s gone!
Featured Highlights
- VIP Access to the Havana Jazz Festival
- Exclusivity: Only 8 Women + Private Boutique Hotel
- Authentic Cultural Immersion
- Walk in Hemingway’s Footsteps
- Savor Cuba’s Culinary Soul
Elegancia Suites Habana
Elegancia Suites Habana, an intimate eight-room boutique hotel nestled in Havana’s tony Vedado district. Built in the late 1940s, the property blends architectural charm with curated sophistication. Vedado’s leafy boulevards, gated residences, and stately mansions offer a serene counterpoint to Old Havana’s bustle.
An Entire Boutique Hotel, All Ours
Inside, you will find a private art collection woven throughout the space—an added delight for design and culture enthusiasts. Tropical Lounge Terrace is the ideal space to enjoy the benefits of our climate, relax, enjoy a cocktail or quell the Havanan heat a bit in the Jacuzzi. There is also a Panoramic Terrace on the roof.
OUR ITINERARY
January 24, 2027
¡Bienvenidas a La Habana! Welcome to the sultry rhythm of Havana! Once you’ve gone through Cuban customs, our friendly driver will be waiting to whisk you away to our chic boutique hotel, tucked away in the heart of Vedado, Havana’s elegant, tree-lined district where vintage charm meets modern flair. Take a little time to settle in, freshen up, and soak in your first glimpses of this captivating city. As the sun begins to dip, we’ll gather for a round of welcome refreshments and discussion of the week’s activities.
Tonight, we’re dining in style at Atelier, a beloved paladar set in a beautifully restored 1928 mansion. From its romantic rooftop terrace, you’ll savor a taste of Cuba’s nouvelle cuisine while soaking up the warm night breeze and city lights. But the night is just beginning! After dinner, we’ll head straight into the heart of the Havana Jazz Festival with a spectacular opening concert featuring some of Cuba’s most celebrated musicians alongside international jazz legends. The energy is electric, the music is soul-stirring, and this is just the beginning of our exciting adventure together! (Dinner included)
January 25, 2027
This morning we’ll begin our day with a hosted breakfast and an inspiring conversation with Marielle Rosemonde, co-founder of Elegancia Suites Habana. She’ll share her powerful journey from the Congo to Cuba, blending entrepreneurship, art, and spiritual traditions to create a soulful boutique experience.
Then, we’ll hop into vintage 1950s convertibles for a glamorous cruise along the Malecón, stopping at El Morro Fortress to shop for premium cigars, rum, and coffee with guidance from a local expert. Next, we’ll enjoy a vibrant seafood lunch with live music at El Rum Rum de la Habana, followed by a guided stroll through the historic plazas of Old Havana including San Francisco, Armas, and Plaza Vieja. Tonight, dine independently at a paladar of your choice, and then we’ll dive into the rhythms of the Havana Jazz Festival with your VIP pass. Remember, the night is yours to explore the venues and sounds that move you most. (Breakfast and Lunch included)
January 26, 2027
After breakfast, we’ll start our day at El Capitolio, Cuba’s grand National Capitol. Explore its opulent halls, the Chamber of Representatives, and the Tomb of the Unknown Soldier, all anchored by the glittering 24-carat diamond marking Cuba’s “kilometer zero.” Next, we’ll dive into four centuries of artistic expression at the Museo Nacional de Bellas Artes, where museum professionals guide us through a curated tour of Cuba’s most treasured works.
Then, we’ll visit the exterior exhibits of the Museum of the Revolution, including the legendary Granma boat and a display of vehicles and artifacts from Cuba’s revolutionary past. For lunch, we’ll unwind at 5 Esquinas Trattoria, a tucked-away Cuban-Italian gem known for its wood-fired pizza, hearty pastas, and Old Havana charm.
This evening, Havana’s rhythms are once again calling. With your VIP JazzFest pass, the night is yours to explore. Whether you’re craving a smooth saxophone solo in a tucked-away club or a bold brass ensemble under the stars, follow your musical instincts: you’re in one of the world’s greatest jazz cities, and every venue holds a new surprise. (Breakfast and Lunch included)
January 27, 2027
This morning, we’ll go behind the scenes at one of Cuba’s top dance companies, where you’ll watch an electrifying rehearsal and meet the talented performers shaping the future of Cuban dance. Then, we’ll enjoy a garden-side lunch at the elegant La Cocina de Liliam, a hidden gem blending Cuban flair with international cuisine, once visited by President Jimmy Carter himself.
The rest of the day is yours to explore Havana’s Jazz Festival at your own pace. From world-class concerts to intimate clubs, follow the music that moves you most. (Breakfast and Lunch included)
January 28, 2027
We’ll begin our day at the stunning Catedral de San Cristóbal, Havana’s iconic baroque landmark honoring Saint Christopher, protector of travelers and a symbol of the city’s spiritual legacy. Next, we’ll explore the historic Taller Experimental de Gráfica, Cuba’s oldest printmaking studio, where revolutionary art, lithography, and local creativity come to life. Meet the artists, learn the history, and perhaps pick up a meaningful print to take home.
Enjoy an independent lunch with your Sisters at a charming café near the cathedral. perfect for relaxing and people-watching in Old Havana. In the afternoon, raise a mojito at the legendary La Bodeguita del Medio, Hemingway’s favorite watering hole, and soak in the vibrant, bohemian spirit of Havana (graffiti walls and all).
As the sun sets, the city once again transforms into a playground for music lovers. With your VIP JazzFest pass, the night is yours to design, whether you want to catch a fiery trumpet solo in an intimate club, or feel the pulse of a big-band performance under the stars. Go solo or grab your Sisters – it’s your Havana, your soundtrack. (Breakfast included)
January 29, 2027
Today, we venture just outside the city to explore the life and legacy of one of Havana’s most famous residents: Ernest Hemingway. In the quiet town of San Francisco de Paula, you’ll step into Finca Vigía, the author’s cherished home and creative refuge for nearly two decades. This is where Papa found peace, inspiration, and a deep connection to Cuba and its people. Tour the estate, see his legendary boat Pilar, and enjoy live music, refreshments, and time to browse for souvenirs.
Next, we’ll enjoy a farm-to-table lunch at Divino, a countryside paladar on La Yoandra ranch, where your meal supports local programs. Stroll the grounds, meet artisans, and savor Cuba’s rural charm. Back in Havana, step into the glamorous past at the iconic Hotel Nacional. In a private salon, join Hemingway expert Gladys Rodríguez for a captivating talk on the writer’s life in Cuba, blending history, politics, and personal stories from his years on the island.
As the afternoon winds down, we’ll return to our hotel for some independent time for perhaps a quiet moment on the rooftop terrace or a sunset stroll along the Malecón. Tonight, the Jazz Festival once again beckons. With your VIP all-access pass, explore the Havana nightlife at your own pace. Follow the music that moves you whether it’s a sultry solo in a candlelit club or a full ensemble playing under the stars. (Breakfast and Lunch included).
January 30, 2027
We’ll begin our day at the Galería Raúl Corrales, where Fidel Castro’s former photographer captured the soul of the Revolution. Meet Claudia Corrales, the artist’s granddaughter, for a personal look at these powerful images and stories. Then, sip a daiquiri “Papa style” at El Floridita, Hemingway’s iconic hangout—complete with a photo op at his favorite barstool.
Enjoy lunch on your own with your Sisters in vibrant Central Havana and then step into Old Havana glamour at Sloppy Joe’s Bar, a restored gem with Hollywood roots and timeless charm.
Spend your afternoon with your Sisters strolling the Paseo del Prado, where local artists transform the promenade into a colorful open-air gallery. Wrap up with a rooftop refreshment at Hotel Parque Central, taking in panoramic views of El Capitolio, the Gran Teatro, and Havana’s historic skyline before returning to the Elegancia.
This evening, your VIP Jazz Festival pass gives you access to yet another dazzling array of performances. Let your heart (and ears) guide you—whether it’s an intimate trio in a tucked-away club or a bold ensemble playing under the Havana stars. (Breakfast included)
January 31, 2027
This morning, you’re in for a treat as we travel east to Cojímar, the seaside village that inspired The Old Man and the Sea. Visit the harbor where Hemingway’s Pilar once docked, see the bronze bust built by local fishermen, and stop at La Terraza, his favorite seaside bar.
Next, we’ll explore the lush organic garden of brothers Jesús and Julio, who grow produce for both their restaurant and local community programs. Then, get hands-on at beloved El Ajiaco with a cooking class and mojito-making lesson, followed by a hearty, flavor-packed Cuban lunch. On the way back to Havana, we’ll pause at Casablanca for panoramic views and a visit to the towering Christ of Havana statue.
After some afternoon downtime, we’ll reunite for a stunning Farewell Dinner at Paladar Vistamar, where ocean views, candlelight, and elevated cuisine set the tone for our final evening. Finally, we close out this unforgettable journey with a major JazzFest finale, celebrating Cuba’s world-class music, vibrant spirit, and the Sisterhood we’ve created together. (Breakfast, Lunch, and Dinner included)
February 1, 2027
After one last delicious breakfast together, we’ll bid farewell to our elegant home in Vedado and transfer to the Havana airport for our journeys home. As we leave the Pearl of the Antilles, we carry with us so much more than souvenirs. We take home the rhythm of the music, the flavor of the mojitos, the laughter shared over rooftop dinners, and the stories whispered through the streets of Old Havana. Most importantly, we take the bond we’ve built with each other: a Sisterhood strengthened by shared adventure, discovery, and joy. Until we meet again… ¡Hasta pronto, Cuba! (Breakfast included)
Trip Inclusions
- 8 nights/9 days single occupancy accommodations at Elegancia Suites Habana, exclusive only to our group
- 15 Meals (8 Breakfasts, 5 Lunches, and 2 Dinners)
- Round-trip airport transfers as specified in the itinerary
- Porterage at hotel
- Mandatory Cuban Visitor Visa
- Jazz Festival VIP Pass with premium seating at all festival venues and performances
- All sightseeing tours, exclusive experiences and excursions as listed within this itinerary which adhere to all U.S. government regulations for a legal visit to the Republic of Cuba
- WIFI at our hotel
- Deluxe, private transportation throughout the itinerary
- Private Tour Director
- Sisterhood Travels Group Leader
- Sisterhood Travels Swag
DEPOSITS & PAYMENTS
- Non-refundable deposit due at time of booking: $1000 per person
- 2nd Non-refundable payment due on or before March 24, 2026: $1000 per person
- 3rd Non-refundable payment due on or before June 24, 2026: $1500 per person
- Final payment due on or before October 24, 2026
PRICING
Single Occupancy with Shared Bathroom-
HAVANA JAZZFEST 2027
PRICING
Single Occupancy with Private Bathroom-
HAVANA JAZZFEST 2027
important information
PLEASE READ THIS INFORMATION CAREFULLY
- There will be a maximum of 8 Sisters including your Sisterhood Travels Group Leader. Single Occupancy only for all participants.
- Because of the nature of our Visa, this trip is only open to U.S. citizens holding a valid American passport.
- International airfare is not included in your pricing. You will fly roundtrip Havana (HAV). When you book your flights to Havana, you will be asked for the reason for your visit. You must select “Support of the Cuban People.”
- This is a legal tour that prohibits you from obtaining pre- or post-nights in Cuba.
- You should plan to arrive by mid-afternoon on January 24, 2027 so that you do not miss our Welcome Dinner and orientation, and you can depart at any time on February 1, 2027.
- Check-in time at our arrival hotel is at 3:00 pm.
- All international flight arrangements must be submitted to Sisterhood Travels on or before October 24, 2026. If you need help making flight arrangements, or to submit your independent flight arrangements, please click here for Airfare Information.
- You are required to have a Cuban Visitor Visa to enter Havana which is included in your pricing. We will provide you with what you need to present to Cuban immigration officials.
- Complete valid passport information is required on or before June 24, 2026. Your passport must be valid for at least 6 months beyond the dates of February 1, 2027. Failure to provide this information by the due date may result in our inability to secure your mandatory Cuban visa and any penalties incurred will be at your expense.
- Arrival transfers are provided only on January 24, 2027 from the Havana airport to our hotel. Departure transfers are only provided on February 1, 2027 from our hotel to the Havana airport. You are prohibited from making other arrangements on your own.
- Cuban Jazz Fest organizers historically do not release the program until just before the festival begins. Please be prepared to receive the program upon your arrival in Havana.
- You may NOT schedule any activities on your own. You are required to adhere to the itinerary provided to you at the start of our tour.
- Individual gratuities for your Tour Director, local guides, drivers and others are not included in your pricing. We will provide you with very detailed, expected tipping guidelines for your trip to Cuba. You must bring USD in cash to Cuba to pay for your gratuities as you will not be able to obtain cash from an ATM.
- U.S. credit cards are not generally accepted in Cuba. You should be prepared to pay for everything with USD in cash.
- Cuban Emergency Medical Insurance is included in the cost of flights originating in the United States. Your airline boarding pass is proof of this coverage and must be presented at a clinic or hospital should you need medical assistance. This emergency medical insurance DOES NOT include coverage for trip cancellation and other services such as repatriation back to the United States. Comprehensive Travel Insurance is strongly recommended for this trip and is not included in your pricing. We will send you a quote via email.
- We cannot accommodate wheelchairs, assistive devices, scooters, walkers or rollators, or Zimmer-frames. You must be able to ambulate independently with no assistance from devices or others on the trip. It is imperative that you read the activity level description below.
- There are no refunds for unused portions of this tour.
- Dates and times of itinerary as well as hotels listed are subject to change without notice due to operational, weather, or logistical reasons.
- Any optional expenses or expenses related to anything not specifically listed in this itinerary are not included.
- You will receive an invitation soon after you book your trip for our travel app, “Trip Plans”. You will need to download this app to your smart phone as this is where you will find the most up-to-date, accurate information regarding your itinerary in addition to all of the critical information you need to know.
Need a Roommate?
Cancellation & Refunds
Activity Level:
Moderate
This unforgettable journey through Havana during JazzFest week and the surrounding countryside is designed for women who are comfortable with a mix of cultural sightseeing, lively music-filled evenings, and immersive local experiences.
Walking & Standing:
Expect moderate walking most days, often along cobblestone streets, uneven sidewalks, and through historic districts. Guided tours of Old Havana’s plazas, museums, and cultural sites may require standing for extended periods. Some evenings include concerts or performances where you may be on your feet for part of the show. Vintage car rides and coach transfers reduce the amount of continuous walking, but participants should be prepared for up to 2–3 miles of walking on sightseeing days.
Terrain, Transport & Accommodations:
You’ll experience a variety of terrain, from polished marble halls of El Capitolio to uneven cobblestones in Old Havana and outdoor rural paths during our countryside excursions. Touring also includes visits to historic homes, cathedrals, and art studios, often with stairs and limited elevators. Our exclusive accommodations at Elegancia Suites Habana do not have an elevator, and some rooms are accessible only by stairs. Travelers should be prepared for stair use on a daily basis. Transportation throughout the itinerary includes private coach, vintage convertible cars, and short walking segments between attractions.
Jazz Festival Evenings:
Your VIP JazzFest pass allows you to attend world-class performances each night. While participation is optional, evenings can be late, and navigating between festival venues may require additional walking and standing in lively crowds. You may tailor your evenings to your own energy level—whether enjoying a single set in a cozy club or exploring multiple stages.
Pace & Considerations:
This program is best suited for travelers who are comfortable with full days of cultural engagement, paired with free time for independent exploration. The combination of music-filled nights and active sightseeing days requires good stamina, and travelers should be able to manage stairs at the hotel and at historic sites. Flexibility is built into the schedule to allow for rest as needed.
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.