Cuba 8 Day Tour


Dec 2-9, 2017

$5,989 – base price

This sublime itinerary packs many of Western Cuba’s most quintessential sites into one week, beginning with such iconic Havana landmarks as the H. Upmann cigar factory, Plaza de la Revolución, and Ernest Hemingway’s former home. Then head west through the mountains to Viñales—a stupendously beautiful valley in the heart of tobacco country. Another highlight is your ride through the Zapata swampland to the Bay of Pigs, site of the failed 1961 CIA-sponsored invasion and a chance to laze on a sugar-white beach. We’ll also visit the monument and mausoleum of Che Guevara in Santa Clara. Plus, we’ll savor a visit to the tranquil colonial city of Trinidad before heading back to Havana via the peaceful bayside city of Cienfuegos.


base price

What's Included?

  • Overnight stays in hotels/casas particulares
  • All breakfasts plus specific meals as listed
  • Motorcycle rental including unlimited kilometers
  • Motorcycle insurance (no deductible on damage)
  • Local Cuban guide on motorcycle acting as lead, plus Christopher P. Baker as Cuba expert and sweeper
  • Support bus for shuttle services and luggage transport, including driver
  • State-approved guide in support bus
8 Day Cuba Tour Map


Day 1

Arrive Havana

This afternoon we meet at our hotel, the Four Points by Sheraton. After our introductory briefing, we’ll mount our bikes for a get-acquainted ride around Havana, taking in such highlights as the Plaza de la Revolución and seafront Malecón boulevard. This evening we’ll dine at one of Havana’s most exclusive paladares (private restaurants).
Overnight: Four Points by Sheraton
Meals: D

**Travel to Havana is individual’s responsibility. PLEASE BE SURE TO ARRIVE AT LEAST ONE DAY PRIOR**

Day 2

Havana – Viñales

This morning we visit a cigar factory to watch torcedores hand-rolling such world-famous cigars as Montecristos, Romeo y Julietas, and Cohibas. Then head to the lovely mountain community of Las Terrazas, where we’ll learn about this remarkable sustainable community project and meet with Chris’ friend, world-renowned artist Lester Campa. Then continue along the Autopista for a delicious typical Cuban lunch at Finca Pinar San Luis, a tobacco farm outside San Luis y Martínez. Here Chris introduces us to his pal Hirochi Robaina, the most famous tobacco farmer in Cuba. We then follow a thrilling mountain route to to Viñales, boasting Cuba’s most exquisite scenery.
Overnight Casas particulares (private home B&Bs)
Meals: BL

Day 3


Today we’ll enjoy riding via the Costera Norte (north coast road) to Jaimanitas, on the western outskirts of Havana. Here enjoy a delicious family-style lunch at Fusterlandia—the remarkable studio-home of artist José Fuster. We’ll then head east along the Autopista (freeway) for Playa Larga (one of the Bay of Pigs invasion landing sites), where we’ll learn about Cuba’s conservation programs with Frank Medina, Director of Parque Nacional Zapata (Cuba’s largest national park, preserving the largest swamp in the Caribbean). This evening relax over beers beachside!
Overnight: Casas particulares
Meals: BD

Day 4


Another exciting day today as we head along the Caribbean shore to visit the excellent Museo Playa Girón telling the Cuban version of the failed CIA-sponsored Bay of Pigs invasion of 1961. Then through gorgeous farmland to El Nicho, a stunning waterfall at the base of the Sierra Escambray mountains. We’ll visit the Grupo Teatro de Los Elementos—a fascinating cultural program in a rural hamlet—then continue to Santa Clara to visit revolutionary icon Che Guevara’s mausoleum and museum.
Overnight: Villa Gaviota
Meals: BL

Day 5


Our route winds through lovely countryside and up through the rugged Alturas de Banao mountains. Emerging in the superbly scenic Valle de los Ingenios (Valley of the Sugar Mills), we’ll explore Sitio Histórico Guaimiro, a restored 18th-century sugar plantation home. We arrive in time for lunch in Trinidad—the perfectly-preserved crown jewel of Cuban colonial cities. You’ll have time to explore this UNESCO World Heritage Site at and dine at leisure, perhaps hosted by the local families with whom we overnight.
Overnight: Casas particulares (private homes)
Meals: BL

Day 6


Today we’ll head along the Caribbean shore to the lovely port city of Cienfuegos, where we’ll learn about baseball in Cuba from one of Chris’ friends—a former national team pitcher. We then head back to Havana via the Autopista, stopping en route to visit Museo Ernest Hemingway—the author’s former home on the southeast outskirts of Havana. Dinner is at leisure.
Overnight: Four Points by Sheraton
Meals: BL

Day 7


This morning we’ll ride to Habana Vieja, the city’s remarkable cobbled colonial quarter, which we’ll explore on foot, including a visit to the Taller Experimental de Gráfica—a superb graphic workshop. We’ll lunch at Azúcar, overlooking Plaza Vieja, then visit to a fascinating mechanic’s workshop. This afternoon drop off your bikes. This evening we’ll ride in classic convertible cars for final dinner at one of Havana’s finest private restaurants.
Overnight: Four Points by Sheraton
Meals: BD

Day 8

Depart Havana

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