Wander Across Cuba

Sold Out!
Feb 25 — Mar 05, 2025
9 days
12/12 spots booked
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. [Deposits are non-refundable within 90 days of the tour start date, even if 30 days have not yet passed since the payment date.]
Prepare yourself for the rhythm of Cuba on this exclusive Wandering Earl Tour, an experience you won't find anywhere else!
Navigate the colorful streets of Havana in a classic car
Interact with a wide range of local Cubans, including dancers, students, authors, musicians and more!
Journey through the gorgeous Vinales Valley, known for its distinctive landscapes
Learn about the world of tobacco at a family-run farm
Meet with local people amidst the impressive nature of Cayo Jutia
Stay in unique guesthouses and 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
Dine on traditional Cuban cuisine, prepared fresh at local farms and in local homes
Visit a fishing community where Hemingway found inspiration for "The Old Man and the Sea"

Step into the heart of Cuba on a tour like no other, made possible only through our extensive local contacts. What sets this trip apart are the endless opportunities for genuine connections with local Cubans, in a way that few tourists will ever have a chance to experience. With rare access to local organizations, dance groups, art foundations, local farms and much more, the list of unique cross-cultural activities is long and remarkable.

We’ll enjoy delicious home-cooked meals in local homes, spending time with communities of artists, students, fishermen and farmers and cruising the streets in classic convertible cars.

Days will be filled visiting the colorful and various neighborhoods of Havana and the spectacular and tranquil nature of Vinales Valley, as well as spending time in a variety of towns and villages in between.

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 excellent restaurants.

In addition, time will be spent discovering the world of tobacco cultivation, visiting coastal communities, immersing ourselves in Cuba’s rich musical heritage, and much more.

Each day promises a wealth of opportunities to connect with the Cuban people, marvel at the stunning natural scenery, and learn all about the rich history of this country.

And it will all be done with the flexibility and relaxed style of a Wandering Earl Tour, allowing for the journey to be enhanced through surprises and unpredictable moments that arise along the way!

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Pay a deposit of $500 per person
  • 1
    Feb 25Havana (arrival day)
    Havana (arrival day)
    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.
  • 2
    Feb 26Havana
    Havana
    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.
  • 3
    Feb 27Havana » Viñales
    Havana » Viñales
    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.
  • 4
    Feb 28Viñales
    Viñales
    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 Rio. 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.
  • 5
    Mar 1Viñales
    Viñales
    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 embrace good fortune, making 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.
  • 6
    Mar 2Viñales » Havana
    Viñales » Havana
    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.
  • 7
    Mar 3Havana
    Havana
    Highlights: Folk dances, University of Arts of Cuba, home-made dinner, 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.
  • 8
    Mar 4Havana
    Havana
    Highlights: Cojimar fishing village, free afternoon, 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.
  • 9
    Mar 5Havana (departure day)
    Havana (departure day)
    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.

Tour Essentials

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.

What's included

Included
  • Wandering Earl Tours group leader
  • Small group (maximum 10 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
Not Included
  • Flights to/from Cuba
  • Passport/visa fees
  • Meals and activities not mentioned
  • Cuban travel insurance (mandatory)
  • Other gratuities