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April 22 – April 29, 2025

Newsweek Readers Choice Best Women's Travel Club

Unforgettable Havana:
A Women-Only Journey of Culture and Connection

Join Us for a Unique Adventure Filled with Art, History, and New Friendships

Join Stacey Ray, our founder and CEO, for Sisterhood Travels’ exclusive women-only tour to Havana in 2025, a journey “In Support of the Cuban People” fully licensed by the U.S. and Cuban governments. This unique adventure offers American citizens a rare chance to explore Cuba’s vibrant culture, meet its people, and immerse themselves in the island’s rich artistic and historical heritage. These once-in-a-lifetime experiences have been specially created for our Sisters, creating magical moments of camaraderie and connection with like-minded women and new best friends.

Arrive in Havana and enjoy welcome refreshments on the rooftop of our hotel, Palacio De Los Corrredores overlooking Plaza San Francisco and the Bay of Havana, followed by dinner at Atelier. The next day, wander the cobblestone streets of Old Havana, a UNESCO World Heritage Site, and visit landmarks like the Taller Experimental de Grafica and the Floridita, Hemingway’s favorite bar. Cruise the city in classic 1950s American cars and experience the El Canonazo ceremony at the Fortress of San Carlos de la Cabana, sharing the joy and excitement with your new Sisters.

Bay of Havana

Delve into Hemingway’s world with a visit to Finca Vigía and enjoy lunch at Divino, a farm-to-table paladar. Discover Havana’s car culture at a classic car restoration workshop and explore Fusterlandia, a mosaic-filled neighborhood. Relax at a private beach retreat at the Tribe Caribe Beach House, complete with a sunset string serenade. Savor a farewell dinner at La Guarida, an iconic restaurant with stunning rooftop views, and cap off your nights with vibrant performances at the legendary Tropicana cabaret and Fabrica de Arte Cubano.

This meticulously curated tour offers an unforgettable blend of relaxation, history, and cultural exchange. Share these extraordinary experiences with your Sisters, forging lifelong bonds and creating cherished memories as you connect deeply with the heart and soul of Cuba.

Trip Highlights

Activity Level

Activity Level 4

Please note that the activity level of 4 “BUSY” is due to the number of planned activities, not because of strenuous physical activity.


April 22, 2025

Today, you should plan to arrive in Havana by early-afternoon. Your guide will have your flight information and will be monitoring your flight arrival in case there is a delay.

You will be met at the airport and transferred to our hotel where you’ll have some free time to get settled. We’ll meet on the Rooftop for welcome refreshments and a tour briefing while enjoying the beautiful view of Plaza San Francisco and the Bay of Havana.

This evening, we’ll enjoy our Welcome Dinner at Atelier, a private restaurant in a home built in 1928. In fact, when President and Mrs. Obama visited Cuba, this restaurant is where the First Lady hosted lunch for Cuban businesswomen. (Dinner is included today)

Hotel: Palacio De Los Corrredores

Plaza San Francisco

April 23, 2025

Start your day with a hearty breakfast at the hotel, fueling up for a journey through the vibrant heart of Havana—Old Habana.

We’ll begin by wandering through the cobblestone streets of La Habana Vieja, a UNESCO World Heritage Site brimming with history and charm. Admire the stunning colonial architecture and lively plazas, each with its own unique story.

From the baroque beauty of the Catedral de San Cristóbal in Cathedral Square to the historic military grounds of Plaza de Armas, every corner of Old Havana offers a glimpse into Cuba’s rich past.

We’ll visit the Taller Experimental de Grafica, the oldest printmaking studio in Cuba, where you can witness the art of lithography up close.

Next, take some time to shop for unique souvenirs at the Cultural Center Old San Jose Warehouses and then visit a premium cigar shop at the historic Castle of the Three Magi Kings of Morro.

Later, we’ll enjoy a seafood lunch together with live music at El Rum Rum de la Habana, before cruising the city in classic 1950s American cars.

We’ll end the day with visits to contemporary art studios, a photography gallery, and a daiquiri at the famous Floridita, Hemingway’s favorite bar.

Finally, we’ll return to our hotel to freshen up before you venture out with your Sisters for dinner and then together, experiencing the traditional El Canonazo ceremony at the Fortress of San Carlos de Cabana. (Breakfast and Lunch included today)

Catedral de San Cristóbal Pano

April 24, 2025

Start your day with a hearty breakfast at the hotel before heading to a rooftop presentation at 9:00 am by a renowned Hemingway scholar, offering deep insights into his Cuban life and works.

Next, we visit Finca Vigía, Hemingway’s cherished Cuban residence, where you’ll explore his personal memorabilia and the iconic boat, Pilar. Lunch awaits at Divino, a family-run paladar on La Yoandra ranch, supporting local community programs. In the afternoon, delve into Havana’s car culture at a classic car restoration workshop, followed by a vibrant visit to Fusterlandia, a mosaic-filled neighborhood.

Discover the ceramic artistry of Beatriz Santacana in her Miramar studio before returning to the hotel. Dinner will be a culinary delight at Café Laurent, offering Cuban-Spanish-Mediterranean fusion with stunning penthouse views. Cap off the evening with a mesmerizing jazz performance at La Zorra y El Cuervo, a top Havana jazz club. (Breakfast, Lunch, and Dinner included today)

April 25, 2025

Today is our Private Beach Retreat! After breakfast at the hotel, we’ll escape to a hidden gem just 25 minutes east of Havana. At the restored 1950s Tribe Caribe Beach House, our private beach retreat on Tara Beach offers us luxurious private cabanas with plush towels and lounge chairs. Beer, wine, or fresh juice, and cold water will be available throughout the day.

Immerse yourself in the serene atmosphere filled with locally sourced furniture, fresh plants, and original Cuban artwork. We’ll enjoy a lunch of grilled chicken, seafood, and vegetables prepared by private chefs on a built-in BBQ grill in our private courtyard, which also features a badminton court and a cozy lounge area.

As the sun sets over the turquoise Caribbean, savor the view from the Grand viewing deck. Our magnificent day will end with a sunset string serenade by a sextet of island musicians, creating an unforgettable soundtrack for our retreat. Dinner is on your own with your Sisters, with several private restaurants within walking distance of our hotel. (Breakfast and Lunch included)

April 26, 2025

We’ll start our day with breakfast at the hotel before heading to Cojimar, a charming fishing village east of Havana that inspired Hemingway’s “The Old Man and the Sea.” Here, we’ll explore the harbor where Hemingway’s boat, Pilar.

Next, discover the organic garden tended by brothers Jesus and Julio, who grow produce for their restaurant and the local senior center. Enjoy a hands-on cooking and mojito-making class at the renowned paladar El Ajiaco, where you’ll create and savor traditional Cuban dishes.

On our return to Havana, we’ll stop at Casablanca to admire the Christ of Havana statue and its panoramic views.

After a break at the hotel, we’ll cap off the night at Fabrica de Arte Cubano (FAC), a vibrant art gallery and nightclub featuring live performances, exhibitions, and tapas. (Breakfast and Lunch included today)

April 27, 2025

We’ll begin our day with breakfast at the hotel before a rooftop presentation by a University professor on “Empowering Women in Cuba,” highlighting progress, challenges, and opportunities.

Then, visit a local produce market to explore the Cuban food ration system and understand the country’s agricultural dynamics. Enjoy lunch at La Cocina de Liliam, a charming paladar known for its Cuban and international cuisine.

Return to the hotel briefly before visiting the historic Hotel Nacional de Cuba. Sip a cocktail and delve into its storied past, from mafia meetings to nuclear brinkmanship.

End the day with dinner at the seaside paladar Vistamar, followed by a spectacular night at the Tropicana, a legendary cabaret showcasing vibrant Cuban culture with dazzling performances under the stars. (Breakfast, Lunch, and Dinner included today)

Local Market

April 28, 2025

Begin your day with breakfast at the hotel, followed by a 9:00 am rooftop presentation on “The Revolution and Cuban Society Today” led by a University of Havana professor, offering insights into the Revolution’s 65-year impact and future prospects.

Next, visit the Museum of the Revolution to see the historic Granma boat and various revolutionary artifacts. Enjoy lunch at Ivan Chefs Justo, a private restaurant with eclectic decor and a rich history.

After some free time at the hotel, conclude your Cuban adventure with a farewell dinner at La Guarida, the iconic setting of “Strawberry and Chocolate,” known for its celebrity visitors and stunning rooftop views.

Disfruta de la noche—enjoy your last night in Cuba! (Breakfast, Lunch, and Dinner included today)

April 29, 2025

Today, our time together sadly comes to a close. We’ll be transferred to the Havana airport for our return flights home. (Breakfast included)

Trip Inclusions


Are you ready for an unforgettable adventure? This trip might be perfect for you! We encourage you to read through the entire itinerary, watch the following video, and carefully review the important information below. While we aim to offer enriching and exciting experiences, it’s essential to ensure this Havana journey aligns with your travel preferences and expectations. Let’s discover together if this trip is your ideal fit!



Double Occupancy
$ 4999
per person


Single Occupancy
$ 5999
per person

important information


  • There will be a maximum of 24 Sisters including your Sisterhood Travels Group Leader. Roommate matching is available.
  • You will be 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.
  • Your passport must be valid through at least six months from the date of April 29, 2025. You will need to present it frequently in Havana.
  • International airfare is not included in your pricing. You will fly roundtrip Havana (HAV). WHEN YOU BOOK YOUR FLIGHT TO CUBA, you will be asked for the reason of your visit. You should select “Support of the Cuban People”.
  • We strongly recommend that you arrive by early-afternoon on April 22, 2025, so as not to miss our Welcome Dinner. You may depart at any time on April 29, 2025.
  • Check-in time at our arrival hotel is at 3:00 pm.
  • This is a legal tour that prohibits you from obtaining pre- or post-nights in Cuba.
  • All international flight arrangements must be submitted to Sisterhood Travels on or before January 15, 2025. If you need help making flight arrangements, or to submit your independent flight arrangements, please click here for Airfare Information.
  • Included arrival and departure transfers are provided only on April 22 and April 29 between our hotel and the Havana airport. You may NOT make other arrangements on your own.
  • You may NOT schedule any activities on your own. You are required to adhere to the itinerary provided to you at the start of your tour.
  • Individual gratuities for your Tour Director, local guides, and drivers 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 tips.
  • 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. We will send you a quote for comprehensive coverage.
  • We cannot accommodate wheelchairs or assistive mobility devices on this trip.
  • 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 4

Activity Level:


This is a consistently robust itinerary that is likely to be filled with a combination of long, active days, several early hotel departures and some long journeys by coach. There may be limited time for rest and rejuvenation as you explore these amazing destinations. There may be multiple flights and travel by non-traditional means such as safari vehicles, rickshaws/pedicabs, etc. Guests should have reasonable health and mobility and be capable of walking 1-2 miles over time over potentially difficult terrain which may include hills. Guests should be comfortable with standing for longer periods of time with no difficulty.