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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
$5890
Price – Shared room
$5400
Book with Confidence
To reserve your spot, a deposit will be required. However, you can book with peace of mind as the deposit is refundable – minus a 3% transaction fee – for 30 days. Balance payments are due 90 days before the tour start date. For 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
Stay in unique guesthouses (casas particulares), offering an authentic glimpse into local life
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)
Nov 11
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
Nov 12
Highlights: Havana tour, 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. We'll then visit a local graphic design studio to meet artists and learn firsthand about Cuba's distinct design aesthetics and traditional printing processes before lunch at a trendy, privately owned rooftop restaurant. After a short break back at our hotel we'll take a leisurely walk along the Prado, Havana's elegant, tree-lined boulevard, where we'll stop to hear an informative overview of Cuba's complex history from a local historian. Dinner will be at one of Havana’s most celebrated restaurants, featuring both excellent food and panoramic views. We'll end the evening at Fabrica de Arte Cubano (FAC), an acclaimed cultural space combining art galleries, live music, and social life, recognized internationally as a leading creative venue.
Havana » Viñales
Nov 13
Highlights: Drive to Viñales, coffee and tobacco farms
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. Along the way we'll stop at Las Terrazas, a sustainable farming community where we'll discuss the local eco-friendly practices over coffee. Lunch will follow at a relaxed café, accompanied by live music. Continuing our drive we'll later visit a working fourth-generation tobacco farm, gaining firsthand insight into the careful process of growing and crafting some of Cuba’s finest cigars. Once we arrive in Viñales, we’ll check into our cozy, locally owned accommodations ('casas particulares'), just steps away from the village center. Our day will wrap up with an authentic Cuban dinner.
Viñales
Nov 14
Highlights: Cuban countryside
Included: Breakfast, Lunch, Dinner
This morning everyone will enjoy breakfast individually in their own casas particulares before we meet to start our day. We'll depart shortly after for a horse or car ride through the Viñales Valley, exploring the area’s stunning natural landscape, known for its distinctive mogote hills, rich farmland, and rural communities. Along the way we'll pause for a deeper discussion about daily life in the Cuban countryside, including local agricultural practices, community dynamics, and rural traditions. Afterwards we’ll head for lunch at a privately owned, multi-generational farm, enjoying fresh dishes prepared from locally sourced ingredients. In the afternoon we'll visit the studio of the "Artist of the Roots," known for creating sculptures carved intricately from tree roots, and learn directly from him about his creative process. The day wraps up with a special dinner experience at the farm home of a local author, where we'll share a meal while surrounded by the peaceful scenery of Viñales.
Viñales
Nov 15
Highlights: Visit to a small island
Included: Breakfast, Lunch, Dinner
After breakfast we’ll hit the road and head north towards the coast. On the way we'll pass through several small rural towns, where we'll get a feel for local life and see everyday Cuban countryside scenes. Once we reach the coast we'll board a boat to enjoy a scenic ride over crystal-clear blue waters to a private beach, where we'll savor a relaxed lunch of freshly caught seafood grilled right by the shore. After spending some leisurely time enjoying the beach, we'll return to Viñales for a late-afternoon rest at our accommodations. Our day will end with dinner together on a spectacular patio overlooking the beautiful, peaceful Cuajani Valley.
Viñales » Havana
Nov 16
Highlights: Drive back to Havana, farm-to-table experience, old Havana
Included: Breakfast, Lunch, Dinner
This morning we'll depart Viñales for our return drive to Havana, stopping en route for an authentic farm-to-table experience. Here we'll enjoy a delicious late brunch while learning about honey production and organic farming practices directly from local producers. Upon arrival in Havana we'll check into our accommodations with some free time to relax or settle in. Later we'll head out to explore the lively streets of downtown, soaking in the atmosphere of Old Havana before gathering for a casual pizza dinner in one of the neighborhood's lively spots.
Havana
Nov 17
Highlights: Folk dances, University of Arts of Cuba, optional visit to Tropicana, Children Circus School
Included: Breakfast, Lunch, Dinner
This morning we'll attend a powerful performance by a Cuban folkloric dance group, experiencing their impressive choreography and athletic skill up close, and we'll also spend some time learning about their daily lives and training. Afterwards, we'll visit the University of Arts of Cuba (ISA), established in the 1970s as a hub for music, visual arts, and performing arts. Here a professor will guide us through the campus, and we'll meet students actively engaged in creative projects. Lunch today will be at a privately owned restaurant specializing in Asian-fusion cuisine, offering an interesting twist on traditional Cuban ingredients. Following a short rest at the hotel, we'll visit an inspiring Children's Circus School, where young performers develop their talents in circus arts. Our day will conclude with dinner together at a popular local restaurant known for its authentic Cuban dishes.
Havana
Nov 18
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)
Nov 19
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 12 participants)
Accommodation (8 nights – boutique guesthouse and private casas particulares)
Transportation within Cuba (private vans and classic cars in Havana)
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. There is a maximum of 6 single rooms available on a first-come, first-served basis. Twin and double rooms are available as well where you may share your room with another traveler. These rooms are ideal for couples or friends.
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. Additionally, we'll enjoy a full-day tour in classic convertible cars in Havana.
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 9 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 "support for the Cuban people," which perfectly matches our tour. This approach emphasizes staying in casas particulares and supporting privately-owned businesses which is what our tour focuses on.
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.
