Cuba creates legends and imbues folklore. Everyday items such as a rolled cigar, a glass of rum spiked with sugarcane juice, a colorful classic car become more—gain a near-mythical status and a story that endured in the American consciousness even when Cuba’s doors were closed. With its pulsating physicality, soulful music, and evocative landscapes, it’s not surprising that Hemingway, Graham Greene, Sinatra, and Churchill—legends in their own right—were drawn to Cuba.
Join us on our new Cuba cycling tour and see for yourself why Cuba is not only breathtaking, but legendary. Explore vivacious Havana and its streets paved in revolution. Peddle through spring green fields of tobacco plants where the haunting sounds of vagueros harmonize with the rustling leaves. Stand in front of caves whose eroded faces tell stories of former indigenous inhabitants hiding from invaders. Cycle along white-sand beaches, by crumbling but lavish buildings, and through verdant biospheres on a trip that might leave you speechless even as it turns you into a storyteller.
Please note: this itinerary and activities are subject to change due to factors such as weather, transportation schedules and availability of guest speakers. We always attempt to replace missed activities with similar opportunities that maintain the same spirit of the tour as well as our focus on People-to-People exchanges. This tour is run in partnership with Cuba Aventuras, a local Cuban outfitter.
Havana's bright culture
Valley de Viñales
Alejandro Robaina Tobacco
Museo de Ernesto Hemingway
Pinar del Rio Hotel
or similar accommodation
Day 1: Bienvenido a Cuba! Once we’ve all gathered at the Havana airport, we travel deeper into Havana for our first day of Cuban adventure. Once we’ve satisfied our appetites at a local paladar, or private restaurant, we begin our walking tour of the city. The highlight of our afternoon is Habana Vieja, or Colonial/Old Habana.
Day 2: Havana to Las Terrazas. Our peaceful ride today takes us past Vereda, Caimito, Guayabal and Cayajabos. The undulating path is fairly smooth as we travel along verdant citrus plantations and plots of various other crops. Today is our first People-to-People experience with the manager of a local cooperative. Our trail concludes in Las Terrazas, where we will dine together and have time to enjoy the town.
Day 3: Las Terrazas to Viñales. We set off early today. Our meandering path takes us through La Sierra del Rosario Biosphere Reserve to Bahía Honda, where we stop for lunch. We pass through several beautiful towns such as Cabañas, Palma Rubia, and La Palma as we make our way to Viñales. When we arrive explore some nearby paths and take in the immersive scenery before we get some well-deserved R&R with dinner and a drink before bed.
Day 4: Puerto Esperanza and Viñales. We enjoy a hearty breakfast before once again climbing onto our bikes to explore more of the sprawling karst landscape. Around lunchtime we land in the Puerto Esperanza, a fishing village which serves as a primary port for Viñales. Lodging is in Viñales again this evening, and we return with plenty of time to explore.
Day 5: Viñales to Pinar del Río. Our cycle today takes us through the San Carlos Valley and Cuba’s tobacco mecca San Juan y Martínez. There, we take to our feet and visit the Alejandro Robaina Tobacco Plantation. After our tour, we continue our Cuba cycling tour to Pinar del Río. Check into your hotel before meeting for dinner at a local restaurant.
Day 6: Cycle Pinar del Río to San Diego de Los Banos and shuttle to Havana. We continue our travels through rural Cuba as our cycle today take us along the La Carretera Central highway passing through Herradura, Capilla, and Paseo Real de San Diego until we arrive in Fierro. There we enjoy another People-to-People interaction with local beekeepers. We shuttle back to Havana and enjoy dinner and dancing together.
Day 7: A Day in Havana. In the morning we drive a short distance west to Jaimanitas where we find the fantasy-world of artist José Rodriguez Fuster. After out tour, the next stop is the the Museo de Ernesto Hemingway located in his former home at Finca Vigía. In the afternoon we have time to explore more of old Havana on foot. Late in the day, we start our final night out on the town with classic car tours and a farewell Cuban feast! Today there is an optional ride for those who wish to ride.
Day 8: Enjoy breakfast together, then shuttle to the Havana Airport.
8 Breakfasts | 7 Lunches | 7 Dinners
PP Double Occupancy
Single Supplement fee*
*This is required if you are traveling solo or if you are traveling with someone but require separate beds.