
Cuba Bike Tour
Couples, Friends & Solos
6 days
5 nights
Activity Levels 2-4
Casual Hotels
Cuba Bike Tour
Couples, Friends & Solos
6 days
5 nights
Activity Levels 2-4
Casual Hotels
2025: Nov-Dec2026: Jan-Apr, Nov-Dec

Trinidad's Timeless Landscapes to Havana's Rhythms
Two wheels are your ticket way off the beaten path in this fascinating time warp of a country. Pedal through mangroves and sugarcane fields, beside dazzling beaches and down the thoroughfares of Old Havana.
Highlights
- Join Cuban pro cyclists from the Cuban Masters Cycling Club for six full days of riding with locals
- Tour a historical what’s-what of the island, including the site of the Bay of Pigs landing and no fewer than four World Heritage Sites
- Chat with journalists and artists, move to the sound of live Cuban rhythms and maybe even indulge in a cigar tasting
- Pedal through the sleepy green landscape of central Cuba, where lush fields and tropical groves are broken up by dome-shaped mountains
- Sit back and take advantage of our years of experience offering US-approved itineraries in Cuba under the “Support for the Cuban People” visiting license

Start/End Havana
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary

Days 1-2
From our meeting in Havana, head straight for the center of the island, where our first ride explores the Valley of the Sugar Mills • Marvel at the abandoned seven-story bell tower in the town of Manaca Iznaga, which once called workers in to lunch from the sugarcane fields • Enjoy some live music in this region considered the cradle of Cuban sounds • Dine alfresco on the sands of Playa Ancón and take to the crystal clear water with snorkels and masks • Tour the cobblestoned center of Trinidad de Cuba, a World Heritage Site.




Nights 1-2
Airy spaces full of boho-chic touches are your private oasis in the World Heritage Old Town of Trinidad.

Day 3
Spin across tropical wetlands and through flooded mangrove forests • Enjoy lunch beneath the trees of a botanical garden • In Cienfuegos, another colorful World Heritage town, the local fortress has stood for centuries as a defense against pirates • Join a tobacco farmer for a presentation on the art of Cuban cigars • Marvel at Cienfuegos’ eye-popping architecture, which mixes French colonial and neo-baroque styles.

Night 3
This rural guest house experience welcomes us into a collection of private Cuban residences with basic amenities such as ensuite bathrooms and air-conditioning—a hybrid somewhere between a homestay and a casual B&B unique to traveling in Cuba.

Days 4-6
Cycle along the coast through sleepy Caribbean fishing villages • Reflect on history when you visit Playa Girón, the site of the 1961 Bay of Pigs landing • Explore the outskirts of Havana, where fruit plantations and sugarcane fields still flourish • Try some of Cuba’s best seafood at a casual but locally beloved beachside eatery • Wander a wonderland of surrealist art at Fusterlandia and share a coffee and a chat with the artist’s family • A meet-and-greet with a local journalist and an urban dance performance bring us below the surface of dynamic Havana • Toast to our week together at an elegant rooftop restaurant overlooking Old Havana • Take a last spin around the city’s iconic landmarks, including the waterfront and the imposing Plaza de la Revolución.



Nights 4-5
An elegantly restored boutique oasis in Havana's modern and well-to-do Vedado neighborhood.
What's Included
See moreStraight Talk
We want to make sure you're on the trip that's right for you. Every Backroads trip is unique and this one is no exception.
In order to travel to Cuba without supporting the Cuban government in a way that would violate the American embargo, we follow an itinerary licensed by the United States Treasury Department’s Office of Foreign Assets Control (OFAC) under a category called “Support for the Cuban People.” The Support for the Cuban People license allows us to travel in Cuba with a planned schedule of meaningful interactions with Cubans. Qualifying for the license allows little room for deviation–especially compared to the flexibility we build into other Backroads itineraries.
When purchasing your flights to Cuba, select that you will be traveling under the OFAC category of “Support for the Cuban People.” You may be able to extend your stay in Cuba beyond the days of our trip depending on your legal status in the US. If you are not extending your stay before or after our Backroads trip, your flight to Cuba must arrive no earlier than the evening before the Backroads trip start and must depart no later than the morning after the trip end.
Cuban roads, especially in the countryside, are very poorly maintained. Come prepared for adventurous riding on gravel, potholes and rough road, which add an extra dimension of challenge to Cuba’s climbs and descents. This is a region for riders of all levels to take advantage of shuttles, to slow down, and to pace yourself and find your line. When in doubt, watch the Cuban Masters Cycling Club members who are riding with us—and bike like a Cuban!
When traveling abroad, things don’t always go according to plan and, particularly in Cuba, itinerary changes or shifts mid-trip are quite common. In the event of a last-minute change to scheduled activities, your leaders will find alternative activities. Expect the unexpected in this region—it’s all part of the adventure!
One of the most notable restrictions for American travelers in Cuba is the State Department’s prohibition on staying in state-associated businesses, which encompass nearly all hotels in Cuba. To respect this requirement, on this trip we stay in privately owned and operated casas particulares, a uniquely Cuban form of accommodation in which locals open up rooms to welcome visitors into their homes. While some casas particulares in Havana are practically indistinguishable from boutique hotels or bed and breakfasts, those in the Cuban countryside are much more basic–a uniquely rustic and local experience as compared to even the most Casual accommodations used by Backroads.
Hotels
Adventure-Ready Hotels
Ideally located with ready access to trip activities, our Casual hotels are also known for their character and charm.
Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.
Nights 1-2
Casual Hotel
Airy spaces full of boho-chic touches are your private oasis in the World Heritage Old Town of Trinidad.

Night 3
Casual Hotel
This rural guest house experience welcomes us into a collection of private Cuban residences with basic amenities such as ensuite bathrooms and air-conditioning—a hybrid somewhere between a homestay and a casual B&B unique to traveling in Cuba.
Nights 4-5
*Deluxe Hotel
An elegantly restored boutique oasis in Havana's modern and well-to-do Vedado neighborhood.
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Bikes
Ready to Ride
On this trip where Backroads custom titanium bikes are not available, we offer local bikes that are well suited for the terrain on our routes.

Included in your trip price
Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
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