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Prepare yourself for the rhythm of Cuba on this exclusive Wandering Earl Tour, an experience you won't find anywhere else!
Step into the heart of Cuba on a unique tour made possible only through our extensive local contacts. What sets this trip apart are the countless opportunities for genuine connections with local Cubans—experiences that few tourists ever have the chance to encounter. With exclusive access to local organizations, dance groups, art foundations, farms, and much more, the list of remarkable cross-cultural activities is long and diverse.
We’ll enjoy delicious home-cooked meals in local homes, spend time with communities of artists, students, fishermen, and farmers, and cruise the streets in classic convertible cars.
Our days will be filled with visits to Havana’s vibrant neighborhoods, the stunning natural beauty of Viñales Valley, and time spent in various towns and villages along the way.
We’ll wander through the lush Havana forest, explore art at the Fabrica de Arte Cubano, visit a circus school, and savor traditional Cuban cuisine at exceptional restaurants.
Additionally, we’ll discover the world of tobacco cultivation, visit coastal communities, immerse ourselves in Cuba’s rich musical heritage, and much more.
Each day offers a wealth of opportunities to connect with the Cuban people, marvel at breathtaking natural scenery, and dive deep into the country’s fascinating history.
All of this will unfold with the flexibility and relaxed style of a Wandering Earl Tour, allowing the journey to be enriched by surprises and spontaneous moments that arise along the way!
Price – Single room
$5990
Price – Shared room
$5530
Book with Confidence
To reserve your spot on a tour, a $500 deposit will be required. However, you can book with complete peace of mind as this deposit will be refundable – minus a 3% transaction fee – for 30 days. For our complete payment/refund policy, please READ HERE.
If you make a deposit for a tour within 90 days of the tour start date, the deposit is non-refundable.
Navigate the colorful streets of Havana in a classic car
Dine on traditional Cuban cuisine, prepared fresh at local farms and in local homes
Journey through the gorgeous Viñales Valley, known for its distinctive landscapes
Learn about the world of tobacco at a family-run farm
Experience the iconic Tropicana, Cuba's legendary cabaret show since 1939, for an unforgettable night
Stay in unique guesthouses (casas particulares), offering an authentic glimpse into local life
Capture the beauty of Havana at sunset with a photo shoot with professional ballerinas
Engage with Cuban artists in their studios, unveiling the depth of the island's creative spirit
Interact with a wide range of local Cubans, including dancers, students, authors, musicians and more!
Visit a fishing community where Hemingway found inspiration for "The Old Man and the Sea" Havana (arrival day)
Feb 24
Arrival day
Included: Dinner
Upon arrival, you'll be greeted at the airport and escorted to our hotel, situated right along the water. After settling in and perhaps enjoying a leisurely walk along the nearby "malecón" — the scenic seawall that runs along Havana's coast — we’ll start off with an evening orientation and a traditional Cuban dinner.
Havana
Feb 25
Highlights: Havana tour, circus school visit, art and culture immersion
Included: Breakfast, Lunch, Dinner
Today a fleet of classic convertible Chevys, Buicks, and Fords will pick us up for an orientation tour of the city, including some places rarely seen by tourists. We’ll navigate through Vedado, an area known for its vibrant streets, historic mansions, and cultural significance. Afterwards we'll head to the lush green Havana forest, brimming with ancient Banyan trees, where we'll have ample opportunities to capture some unique photos with our classic cars. Our journey will continue along the malecón before venturing into Old Havana, passing some of Havana’s most celebrated squares. Following lunch at a trendy rooftop restaurant, we'll digest over a presentation on Contemporary Cuban Photography from Nelson Ramirez de Arellano, the former Director of the Cuban National Center for Photography (Fototeca de Cuba) and presently, the Director of the Havana Biennial. This encounter will offer us a rare, personal glimpse into Cuban art and heritage. In the afternoon, we’ll have a moment to refresh at our hotel before visiting a Children’s Circus School in Old Havana, an inspiring project that trains young performers in the circus arts. Dinner will be at a famous rooftop restaurant near the banks of the Almendares River. Our evening will finish with a visit to Fabrica de Arte Cubano (FAC), Havana’s melting pot of art, music, and culture, acclaimed as one of Cuba’s most successful cultural projects and recognized by Time Magazine as a must-visit global destination.
Havana » Viñales
Feb 26
Highlights: Drive to Viñales, Mogote Arts dinner experience
Included: Breakfast, Lunch, Dinner
Following breakfast, we’ll get into our vans for a 3.5-hour drive towards the Valle de Viñales, known for its red soil and rich agricultural landscape. As we journey, it'll feel like stepping back in time with scenes of oxen pulling carts loaded with tobacco leaves. We’ll also pause at a viewpoint to marvel at the extraordinary mogotes—steep, rounded hills that rise abruptly from the valley floor, defining this UNESCO Heritage Site's skyline. Upon arrival, we'll settle into our comfortable 'casas particulares', private homes offering cozy, local lodging, and situated only a few blocks from Viñales village center. Later in the afternoon, we're off for a special dinner experience at Mogote Arts, the serene home, farm, and art studio of Luis Deulofeu. Luis is a local published author and true renaissance figure within the community. Much of our delicious dinner will be prepared using ingredients from a certified-organic farm.
Viñales
Feb 27
Highlights: Tobacco farm, lunch at a family-run farm, horse ride
Included: Breakfast, Lunch, Dinner
Today we'll delve deeper into the world of tobacco agriculture by visiting the family-run and owned Montesino Farm in Pinar del RÍo. As one of Cuba's most distinguished tobacco producers, the farm offers us an insightful look into the detailed process of turning a seed into a cigar. After our visit, we'll return to Viñales just in time to savor a late lunch alongside some local farmers at another multi-generational, family-run farm. Following lunch, there will be an optional horse ride through the verdant valleys of Viñales. We'll conclude the day with dinner in a charming restaurant nestled within the mogote hills.
Viñales
Feb 28
Highlights: Minas de Mathambre, visit to a small island, local sculptor
Included: Breakfast, Lunch, Dinner
After breakfast, we’ll hit the road and head north towards Cayo Jutia, a stunning coastal region. Along the way, we'll stop at Minas de Matahambre, a small rural town celebrated for its traditional copper mining. As we drive, we'll make stops in various villages to meet local families and experience their way of life. A private boat will then escort us to an island where we'll enjoy a simple, yet delicious lunch of fresh-caught seafood, charcoal-grilled right in front of us. Afterwards, we'll make our way back to Viñales for some free time at our accommodations before venturing out in the early evening. We'll visit a local sculptor, known for his wild creativity and natural tree carvings. Dinner will follow in one of Viñales most peaceful front porch restaurants.
Viñales » Havana
Mar 1
Highlights: Drive back to Havana, sunset photoshoot with ballerinas
Included: Breakfast, Lunch, Dinner
After a leisurely morning, we'll begin our 3.5-hour drive back to Havana, pausing to explore any interesting sights we encounter on our way back. Once we've settled back in Havana, we'll take a late afternoon drive across the bay for a sunset photo shoot that promises some of the best views of the city. During our tour we'll be accompanied by two of Havana’s skilled ballerinas, providing us not only with a stunning addition to our photos but also a unique opportunity to understand the revered art of ballet in Cuban culture straight from the source.
Havana
Mar 2
Highlights: Folk dances, University of Arts of Cuba, optional visit to Tropicana
Included: Breakfast, Lunch, Dinner
This morning we'll be amazed by a performance of the Compañia Ban Rarra, Cuban folkloric dancers from Guantanamo, showcasing their athletic prowess and choreography steeped in Haitian traditions. After lunch at a charming restaurant surrounded by beautiful gardens and some free time, we'll head to the University of Arts of Cuba (ISA). Founded in the mid-1970s with original structures dedicated to music, visual arts, and performing arts, we'll meet some of the students and enjoy a glimpse into their creative projects. Dinner will be a delightful experience at our local guide's house, where we'll indulge in traditional Cuban fare and the island's best canchanchara. Post-dinner, we'll have the option to visit the famous Tropicana, Cuba's quintessential cabaret show since 1939, for an unforgettable night of dance that captures the essence of Cuban culture.
Havana
Mar 3
Highlights: Cojimar fishing village, farewell dinner
Included: Breakfast, Lunch, Dinner
After breakfast, we'll head east towards the fishing base of Cojimar, famously frequented by Ernest Hemingway. It's well-known that Hemingway enjoyed playing dominoes here, and his time in Cojimar is said to have inspired his classic, "The Old Man and the Sea." We’ll dedicate some time to exploring the fishing village before lunch. The late afternoon will be yours to pack, rest, or perhaps make one last visit to Old Havana. We'll then conclude our day with a celebration of our journey’s highlights and a farewell Italian dinner at a renowned restaurant in the Miramar district of Havana.
Havana (departure day)
Mar 4
Departure day
Included: Breakfast
You will be picked up at the hotel by our private driver and transferred to the airport in time for your departing flight.
Wandering Earl Tours group leader
Small group (maximum 10 participants)
Accommodation (8 nights – boutique guesthouse and casas particulares)
Transportation within Cuba (private vans)
Local English-speaking guides in each destination
All included activities and entrance fees
Breakfast every day, 7 lunches and 8 dinners
Gratuities at hotels/included meals
All airport transfers 
Flights to/from Cuba
Passport/visa fees
Meals and activities not mentioned
Cuban travel insurance (mandatory)
Other gratuities 
Medium Physical Level
While the tour itself is not very strenuous, please note that it can involve the following: long days, walking for up to 2 hours at a time in the cities, walking on uneven terrain in the Viñales Valley, being in the sun in potentially hot temperatures, two 3.5-hour drives, a boat excursion to a secluded island, early morning wake-ups and other similar scenarios.
Accommodation
This trip includes a highly-rated boutique hotel in Havana, as well as quality casas particulares in Viñales. A casa particular is a private family residence transformed into a guesthouse. All rooms are comfortable and feature a private bathroom. * Please note: If you book a shared room and we cannot find another traveler to share that room, there will be an extra surcharge for having a single room.
Transport
During the trip, we'll travel in comfort in private vans in order to ensure flexibility, plenty of space for each guest and access to areas that larger vehicles simply can't go.
Meals
Breakfast every day, 7 lunches and 8 dinners are included. With included meals, some will be served family style and other times you will be able to order from a menu. All dietary restrictions can be accommodated although it might result in a limited menu.
Sustainability
As with all of our trips, we aim to offer as sustainable an experience as we can. Trash is recycled where possible and we avoid mass tourism activities that cause harm to the environment and/or do not benefit local communities.
Small Groups
This tour requires a minimum of 8 participants and has a maximum of 10 participants in order to ensure the best small group tour experience. With such a small group, you'll be able to enjoy unique, rewarding activities that would not be accessible with more people. That's the kind of trip we love to offer!
Rules for US Citizens Visiting Cuba
US citizens are legally allowed to visit Cuba through one of 12 authorized categories, including "People to People" tours and "support for the Cuban people," which perfectly matches our tour. Our Cuba tours strictly follow all required regulations.
Itinerary Changes
While we do our best to follow the itinerary, changes may be made to any aspect of the tour due to a variety of potential situations or unforeseen circumstances.
