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Enjoy Cuba's unique culture

Long Weekend In Havana

Land-Based Expeditions
Enjoy Cuba's unique culture

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Long Weekend In Havana

Allow yourself to be swept away by the profoundly original traditions of Havana! In just one long weekend, on International Expeditions’ new people-to-people Cuba tour, you can chat with artists in their studios, survey Hemingway’s former home and favorite bars, and discover the history of Cuba’s famed cigars and rum. Highlighting the journey are opportunities to mingle with Cuba’s new generation of entrepreneurs – restaurant owners. Family run paladars offer the best cuisine, plus chances to discuss the changing face of Cuba’s economy with private business owners.


Daily Itinerary

Long Weekend in Havana

  • Day

    Arrive Havana

    Fly to Havana, where we are met by our Cuban guide.  Discuss Havana’s past and future while en-route to lunch. Delve into the percussive rhythms of Afro-Cuban dance and music at Habana Compass Dance, a private school of dance, where we attend rehearsals and meet the director. Stop at Cementerio de Colon to see some of the vast array of monuments and works of art in architecture located here. Designed by Spanish architect Calixto de Loira in the mid-1800s, it is laid out in grids around a central chapel a short visit here gives a great sense of the history of Havana’s wealth and love of artistic expression over the centuries. Enjoy dinner in Old Havana before a guided evening stroll. Spend the next four nights in refined accommodations at the Melia Cohiba, just steps from the Malecon. (L,D)


  • Day

    Old Havana

    Discover 500 years of history and architecture while exploring Havana. Stroll along the meandering streets to Plaza de San Francisco, stopping to pay your respects to the bronze statue of El Caballero de Paris (the Gentleman of Paris) and learn about the interesting story of why he was immortalized. In Plaza de Armas, your local Cuba tour guide discusses the city, founded here in 1519. Continue a leisurely stroll through the main squares of Old Havana. See Hotel Ambos Mundos, where Ernest Hemingway kept a room for years. The hotel served as a refuge for writing and as a base for frequenting his favorite bars. From the City Museum to the street vendors trading authentic books and memorabilia that commemorate the Revolution, Plaza de Armas is one of Havana's greatest treasures. Our small group continues to Plaza de la Catedral, the fourth of Havana's wonderful squares. The picturesque plaza usually provides an opportunity to snap a photo with local Habaneros dressed in traditional costumes. Perhaps nothing is more symbolic of Cuba than cigars, and our afternoon is spent at a factory learning about the country's coveted tobacco and the artisanal process by which they are rolled one by one in a process that hasn't changed for centuries. Cap-off our day clowning around with the students and teachers at the Angeles del Futuro children's community project, an afterschool program teaching circus and acrobatic skills to area youth. After dinner at a trendy paladar, dance to the sounds of a Buena Vista Social Club revue. (B,L,D)

    Fishermen at sunset along Havana's malecon
  • Day

    Art of Havana

    Head to the outskirts of Havana to the interesting neighborhood of Jaministas. It was here where he grew up that distinguished artist Jose Fuster launched a community beautification project. The entire neighborhood is a living canvas and our conversations with both residents and local artists focus on the transformative power of art in the lives of ordinary Cubans. Board a ferry bound for the island of Regla, visiting Iglesia de Nuestra Señora de Regla (Church of Our Lady of Regla). Inside this tiny church is La Santísima Virgen de Regla. The virgin, represented by a black Madonna, is venerated in the Catholic faith and associated in the Santería religion with Yemayá, the orisha of the ocean and the patron of sailors. Delve into the modern history of Cuba’s classic cars at a local garage, learning how Cubans keep these classics on the road despite limited resources. Spend the afternoon mingling with locals at a market, where you’ll find artisan-crafted items ranging from modern art to hand-rolled cigars. Looking for an incredible night out in Havana? After dinner, your guide can make arrangements for you to experience the famed Tropicana (at your own experience). (B,L,D)

  • Day

    Classic Havana

    Pay homage to “Papa” Hemingway at his former home Finca Vigia, preserved as it was on the day of his death, and discuss his life with Cuban experts and researchers. Travelers can only peer through the open windows of this museum, but the inside is arranged almost as if the home was waiting for him to return with guests. Hemingway’s fishing boat, El Pilar, is still on the grounds. Back in Havana, Survey Cuban history at the Museum of the Revolution. Housed in the former presidential palace, this is also the site of a failed assassination attempt on Batista in 1957. Hop into vintage classic American cars. Cruise along the Paseo del Prado in Centro Habana passing a variety of landmarks, including the Bacardi Building, Central Park, the Grand Theater and Capitol. Enjoy a visit to iconic Plaza de la Revolucion before a festive farewell dinner. (B,L,D)

    Explore the streets of Havana
  • Day

    Depart Havana

    After breakfast, return to the airport for flights home. (B)


Things to Know

What are the physical requirements of this long weekend in Havana?

A trip to Cuba is an active one that calls for good health. You should be able to walk without assistive devices or the help of others a minimum of two hours at a somewhat brisk pace in order to participate in this expedition. The activities involve a great deal of walking on uneven terrain such as cobblestone streets or slippery trails, and standing, all of which will be in hot weather. You will occasionally have to climb/descend stairs and negotiate places where the footing is uncertain, often times without handrails. 

How much spending money do I need for this long weekend in Havana?

Cuba isn’t cheap for Americans. We recommend that you bring around $750 per person with you unless you know you will be shopping for art, for example, and will need more. While you may not spend this much, there is no way to get more money should you need it. Remember, you do not have the luxury of getting more from an ATM or using a credit card. The cost of your program already includes accommodations, sightseeing and group meals. You will need cash for shopping, bar tabs, items of a personal nature and some gratuities.

Other Expenses

Items of a personal nature such as phone calls, laundry, and some drinks are not included.

What does "People to People" Cuba travel mean?

Without a doubt, the most popular question International Expeditions’ Travel Planners receive has to do with the definition of people-to-people Cuba travel. What is it? What does it mean? How will this impact my experience in Cuba?

The people-to-people initiative allows Americans to travel to Cuba. Every program includes a full-time schedule of educational exchange activities, including interactions with Cuba’s musicians, artists, naturalists and new generation of entrepreneurs. As the name suggests, International Expeditions’ people-to-people travel means that our itinerary focuses on cultural exchanges that will be as educational for the Cubans we encounter as they will be for you! IE’s itinerary allows participants to visit a wide scope of organizations, institutions and community projects, which will provide a deeper understanding of Cuban culture through people and places that the average tourist rarely sees.

Remember: People-to-people travel is not tourist-oriented. There is no time allotted to skip an activity in favor of shopping or beache excursions. IE includes a full-schedule of engaging activities.
Have other questions about legal travel to Cuba? Our Travel Planners are happy to chat anytime.


Melia Cohiba

Meliá Cohíba

Located in Vedado, a modern district in Havana, just steps from the famed  Malecón, the Meliá Cohíba offers stunning views of the city and sea. Fully air conditioned, the hotel provides comfort and an elegant, modern design with Cuban marble and references to the world of cigars and the famous Cohíba brand.

From: $3,999 per person
5 Days, 4 Nights
Guest Capacity
20 Guests
Trip Type
Travel Style
Expedition Destinations

Trip Highlights

  • Discover the transformative power of art during in-studio discussions with Cuban artists & in the famed Fusterlandia neighborhood
  • Survey the atmospheric squares of Old Havana.
  • Channel your inner-Hemingway while visiting “Papa’s” haunts, including the places where he lived while penning The Old Man & the Sea & For Whom the Bell Tolls.
  • Mingle with artisans, craftsmen & private paladar owners.