Cuba| Motorcycle Diaries

Join Cuba expert and moto-journalist, Christopher P.  Baker, on a motorcycle tour of Western & Central Cuba


Map of itinerary

Trip Summary:

Acclaimed Cuba expert and moto-journalist Christopher P. Baker has designed the perfect 12-day motorcycling itinerary of Western & Central Cuba. The “Motorcycle Diaries” redux program includes the Bay of Pigs, plus Santa Clara–with its close association to iconic revolutionary (and motorcyclist) Ernesto ‘Che’ Guevara. We’ll even visit the Comandancia de Che (his former headquarters), plus Cuevas de los Portales (a giant cave where Che headquartered during the Cuban Missile Crisis), along with the enchanting colonial city of Trinidad and the snow-white beaches of Cayo Santa María. We will visit the capital city of Havana and head to tobacco growing country of Viñales and Matanzas.


With two decades experience motorcycling in Cuba, no one knows motorcycling around the island like Christopher. In 1996 he shipped his BMW R100GS motorcycle to Cuba and rode 7,000 miles during a three-month journey to research the Moon Cuba guidebook. His literary travel book–Mi Moto Fidel: Motorcycling Through Castro’s Cuba–describing the journey was published by National Geographic Adventure Press and is a two-time national book award winner.


Seventeen years later, in 2012, Christopher secured a “people-to-people” (P2P) license from the US Department of Treasury’s Office of Foreign Assets Control to offer the first-ever group motorcycle travel of Cuba for U.S. citizens… and a year later finally fulfilled his dream of leading the first-ever such tour of Cuba end-to-end since the Revolution. He has since led numerous group motorcycle tours of Cuba, plus more than 70 “people-to-people” trips to Cuba on behalf of National Geographic Expeditions and other leading international tour companies.

Christopher has authored four other books about Cuba… written feature articles on Cuba for magazines from Motorcyclist to National Geographic Traveler and Playboy… and appears frequently on CNN, MSNBC, NPR and other radio & TV outlets.


Christopher guarantees that joining one of his group motorcycle tours will be immensely rewarding and memorable as he shares with you his intimate knowledge of Cuba.


Your itinerary will include activities that provide a fascinating overview of the history and culture of the country while maximizing interaction with Cubans from all walks of life… from artists, baseball players, and classic car owners to local harlistas (owners of pre-revolutionary Harley-Davidsons).

  • Choice of Harley-Davidson, or Suzuki
  • Approx. 1,000 miles of riding
  • Easily navigated by any experienced touring enthusiast, we’ll travel primarily on paved roads with occasional unpaved sections.

Map of itinerary

Daily Itinerary:

Day 1 | Sunday, October 22 | Havana Begin your journey by checking in mid-afternoon at your hotel. Here, meet your tour leader, Cuban motorcycle guide, and Havanatur tour guide for a welcome orientation. From the airport we will head to El Ajibe for special welcome lunch. Then we will match you with your motorcycle and head out for get-acquainted ride, which will include the Plaza de la Revolución, with its iconic five-story wall mural of Che Guevara. In the evening we have the opportunity to go back in time in convertible classic cars on our way to dinner at La Guarida, considered to be Cuba’s top paladar. A paladar is a small family-run restaurant licensed to provide meals in a private home. Havana Accommodation (L/D)


Day 2 | Monday, October 23 | Havana This morning we enjoy an entertaining presentation about Havana’s history and urban dilemmas by Chris’ personal friend, architect and restoration consultant Pedro Vásquez. Then we’ll ride to Habana Vieja to explore on foot the main colonial plazas. Lunch will be at Restaurante Azucar, a loud, funky restaurant with has one of the most envious views of the Plaza Vieja. We’ll visit the Taller Experimental de Gráfica, a graphic workshop and artists’ cooperative, for an exchange with the printmaking artists, before lunch at a motorcycle-culture-themed restaurant. This afternoon, explore the 20th-century Vedado district, including a visit to a workshop where a prominent harlista (owner of pre-revolutionary Harley-Davidsons) maintains his collection of more than a dozen antique Harleys and other bikes. Dinner will be at Restaurante 1958, with a mixture of  French and Mediterranean cuisine. Havana Accommodation (B/L/D)


VALLE DE VINALES, the lush green UNESCO World Heritage site is arguably one of Cuba's most magnificent natural settings. Besides sweeping valley and rocky landscapes, Viñales offers its visitors glimpses into the rural Cuban farmer. One will see the slow movement of the traditional farmer in the distance, leading his oxen and plough through the many crops of fruit, vegetable, coffee and tobacco plantations. With its traditional single-story farmhouses and warm, friendly people, Viñales is a true gateway into the real Cuba.


Day 3 | Tuesday, October 24 | Las Terrazas / Viñales After breakfast, we depart the city this morning for the most beautiful part of the country; the Viñales Valley. En route we stop at Las Terrazas, an UNESCO Biosphere Reserve and ecological planned community created after the Revolution as a model sustainable community. A guided walking tour includes a visit to the studio-home of Chris’ long-time friend Lester Campa, a renowned artist who will discuss Cuba’s highly successful arts education system. After a superb country lunch at La Fondita de Mercedes, we continue to Viñales, the heart of the Cuban tobacco industry. Before descending into the valley, we stop at the hilltop visitor center for a park ranger’s presentation of Viñales Valley National Park, known for its pine trees and bulbous limestone cliffs. Dinner tonight is at Paladar D’ Olivo. Viñales Accommodation (B/L/D)


Day 4 | Wednesday, October 25 | Viñales Today we ride the twists of the Sierra de Guanguánico as we head into the heart of tobacco country. We’ll meet Chris’s friend Hiroshi Robaina (owner of the most famous and successful tobacco farm in Cuba) to learn about tobacco growing and private farming. We’ll lunch in the peaceful town of Pinar del Río before returning to Viñales for a gathering with local hunters to learn about gun and hunting culture in Cuba. Dinner is on your own. Viñales Accommodation (B/L)


MATANZAS, sometimes called the Venice of Cuba, is home to seventeen bridges that cross its three rivers.  It is also affectionately called the Athens of Cuba, due to it reputation as a center for for poets, culture, and Afro-Cuban folklore.


Day 5 | Thursday, October 26 | Matanzas This morning we head east along the Autopista and wind through the breadbasket of Cuba, to the town of San Antonio de los Baños for an engaging meeting with teachers and young children at the provincial music school. We stop for lunch at Il Divino, a divine paladar on the outskirts of Havana, before continuing along the old Carretera Central to Matanzas. This port city is renowned as a center of African musical culture. This is the focus of our afternoon. Dinner is at Paladar La Mallorca. Matanzas Accommodation (B/L/D)


SANTA CLARA was the site of the last battle of the Cuban Revolution and is where Ernesto “Che” Guevara is buried. There is a mausoleum that houses his remains along with the 16 fellow soldiers, all killed while fighting in Bolivia. 


Day 6 | Friday, October 27 | Santa Clara We will start the day by riding the Circuito Norte, the North Coast Road and en route to Santa Clara, stop for a meeting with the tránsitos (traffic police). We will stop for lunch on your own. We arrive in Santa Clara, a delightful industrial/university city offering a wide range of options for our fascinating afternoon activities. We’ll spend the night and dine at the pleasant Hotel Villa La Granjita. Santa Clara Accommodation (B/D)


Day 7 | Saturday, October 28 | Cayos de Villa Clara Santa Clara is intimately associated with Che Guevara, who led his guerrilla army out of the nearby mountains on December 29, 1959, to capture the city and seal the fate of dictator General Fulgencio Batista. We begin today with a private guided tour at the Museo de Ernesto Che Guevara. Lunch will be on your own, then we ride to the charming colonial city of Remedios and on to the Museo de Agroindustria Azucarera for a presentation on the history of the sugarcane industry and sugar production. Finally we ride over the 30-kilometer-long pedraplen (causeway) that leads over the ocean to Cayos de Villa Clara. Dinner will be at the hotel. Cayos de Villa Clara Accommodation (B/D)


TRINIDAD, in central Cuba, is one of the best-preserved cities in the Caribbean. Dating back to a time when sugar trade was the main industry in the region, it offers exquisite Spanish colonial architecture and warm, friendly people. A day spent within Trinidad’s streets is essential to experiencing the full extent of the Cuban spirit.


Day 8 | Sunday, October 29 | Trinidad Returning along the pedraplen, we ride to Sancti Spíritus, where you’ll have a chance to ride Cuba’s only motocross course with the national motocross champion! After passing through the Valley de los Ingenios (Valley of the Sugar Mills) we arrive in Trinidad, a UNESCO World Heritage City and true colonial gem. Here you’ll spend two nights overnight at a Casa Particular (B&B) with a Cuban family, a true highlight of your journey. Dinner tonight will be at Sol Ananda, the best paladar in town. Casas Particulares (B/L)


Day 9 | Monday, October 30 | Trinidad Chris and our Havanatur guide will lead a walking tour of the colonial core, with visits to Chris’ friend Lázaro Niebla (an astounding artist) and his wife Leanys Hernández (leader of a women’s linen cooperative). We lunch at the breeze-swept hilltop Vista Gourmet paladar before riding to a working cattle ranch this afternoon for a meeting with “horse whisperer” Julio Muñoz, another of Chris’ close friends. Dinner will be on your own. Casas Particulares (B/L)


Day 10 | Tuesday, October 31 | Bay of Pigs – Havana After breakfast, we set out along the Caribbean coast for the city of Cienfuegos. A brief sojourn here includes a private meeting with a former Cuban national baseball team pitcher. Continuing on, we arrive at the Bay of Pigs. Here we visit the excellent museum dedicated to the failed CIA sponsored invasion of Cuba, by Cuban American exiles. Then we have lunch on the beach and enjoy a presentation on environmental issues by the Director of the Zapata Swamp National Park. After relaxing by the sands, we’ll pause briefly at the local crocodile breeding farm, time permitting, before heading back along the Autopista (freeway) to Havana. Dinner on your own. Havana Accommodation (B/L)


Day 11 | Wednesday, November 1 | Havana Your final morning ride will be to the western outskirts of the city to the community of Jaimanitas, nicknamed “Fusterlandia,” and the studio-home of Chris’ close friend José Fuster, known as the “Picasso of the Caribbean.” We’ll even enjoy lunch here! Finally, it’s time to drop off our bikes. The rest of the afternoon is free to shop for cigars and rum, relax or explore Havana. Our farewell dinner will be at Restaurante Le Chansonier—another sensational paladar. Havana Accommodation (B/L/D)


Day 12 | Thursday, November 2 | Havana After one last Cuban breakfast, we bid Cuba farewell. Transfer to the airport for flights home. (B)

Journey Leader

CHRISTOPHER P BAKER Christopher P. Baker has made a career as a professional travel writer, photographer, lecturer, tour escort and moto-journalist since 1983. Christopher—the Lowell Thomas Award 2008 ‘Travel Journalist of the Year’—has been honored by National Geographic as: “One of the world’s leading Cuba travel experts.” His more than two dozen books include six books about Cuba, including his coffee-table book Cuba Classics: A Celebration of Vintage American Automobiles. His many feature articles on Cuba include for magazines from Motorcyclist to National Geographic Traveler and Playboy. He appears frequently on CNN, MSNBC, NPR and other radio and television talk shows. His personal website can be found at

Christopher BakerWS

Journey Details


NOTE: This itinerary is subject to change to take advantage of the serendipity of the moment when we are in Cuba... to meet someone special, to engage in an activity that might occur unexpectedly, or to accommodate circumstances beyond our control. Restaurants or hotels may change in similar category.


INCLUDED: In country transportation per itinerary; eleven night’s accommodations (double occupancy) in premium hotels or casa particulares; Motorcycle rental (tour price varies according to model of motorcycle selected): full breakfast daily plus 9 lunches and 7 dinners (B/L/D per itinerary); Cuban motorcycle guide; expertise of Christopher P. Baker as trip leader, guest speakers; all entrance fees to ventures on itinerary; preparation materials; tips for bellman


NOT INCLUDED: Airfare to and from Cuba; Cuban visa; Cuba airport departure tax, and Cuba medical insurance policy (should be included as part of your air reservation); meals not on itinerary, 4 dinners and 2 lunches (B/L/D per itinerary); alcoholic drinks; excursions not on the itinerary; tips for local guide and staff (optional, yet customary); and Travel Protection.

TRAVEL PROTECTION: For more information on the recommended travel protection plans or to enroll, contact Travelex Insurance Services at 800-228-9792 and reference location number 47-0272.

Please advise Travelex that Cross Cultural Journeys is the travel company for this trip.

Upon request for enrollment Travelex will collect the following information for the traveler(s):

    1. Dates of travel
    2. Name of traveler
    3. Date of Birth
    4. Traveler’s phone number, address, city, state, zip
    5. Reason for travel: Educational: People to People
    6. Name of Travel Agency (Cross Cultural Journeys)

Please note: Insurance for this trip may differ from previous insurance purchases and follows a different process given the destination. In addition, this is a process we must follow as regulated by the Office of Foreign Asset Control for any travel to Cuba.

For a summary of plan details on benefits, coverages, limitations and exclusions, please refer to the applicable Description of Coverage. Travel Insurance is underwritten by Transamerica Casualty Insurance Company, Columbus, Ohio; NAIC #10952. 1308294

Medical and Evacuation insurance is required for this trip. We recommend:

Medjet Assist




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