Cuba Multi-Adventure Tour
Cuba Multi-Adventure Tour
6 days
5 nights
Activity Levels 1-3
Casual & Deluxe Hotels
2025: Nov-Dec2026: Jan-May, Nov-Dec2027: Jan-Jun
Cultural Connections & Havana Highlights
Fields of sugar cane. White-sand beaches and turquoise waters.āÆHistoric Havana. See it on foot, by bike and side by side with the locals. No one immerses you like we do in thisāÆone-of-a-kind country.
Highlights
- Embark on this unique US-approved Multi-Adventure tripāBackroads was the first to launch a trip of this kind!
- Journey from pastoral ViƱales to bustling Havana, biking and hiking between domed karst hills and lush tobacco fields
- Meet farmers and ranchers who share a slice of their rural island worldāincluding a stay at a casa particular, an intimate hospitality experience that makes us guests in a Cuban home
- Hit the islandās best bike routes alongside the ultimate insider guides, the Cuban Masters Cycling Club
- Eye-popping urban art, dance lessons and Q&As with local entrepreneurs and journalists are just a few of the ways youāll immerse yourself in island culture

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

Days 1-2
Hike red-dirt trails amid fields of leafy tobacco and dramatic domed hills (mogotes) ⢠Visit a tobacco farm to learn how the leaves are rolled into cigars ⢠Our agricultural odyssey continues with a glimpse into the cultivation of Cuban coffee ⢠Get to know a family at their prize-winning farm and enjoy a farm-to-table feast ⢠Cycle through ViƱales National Park alongside members of the Cuban Masters Cycling Team, who show us the ropes of being a cyclist in Cuba ⢠Spin to the miles-long, white-sand beaches of Cayo JutĆas ⢠In the evening, join the locals for live Cuban music.

Nights 1-2
This rural guest house experience welcomes us into a collection of private Cuban residences with basic amenities such as ensuite bathrooms and air-conditioningāa hybrid somewhere between a homestay and a casual B&B unique to traveling in Cuba.

Days 3-6
Enjoy a fresh-caught seaside lunch before cycling into Havana ⢠Discuss art and its influence during a visit to the surreal community installation of JosĆ© Fuster, dubbed the Picasso of the Caribbean ⢠Ride into the pastureland surrounding the capital, where a farm-to-table lunch awaits among the sugarcane ⢠Join a local geopolitical professional for an informative Q&A session ⢠Explore vibrant Habana Viejaāending in the Plaza de Armas, Havanaās oldest squareāwith a local expert and witness the preservation efforts firsthand ⢠Entrepreneurs andāÆpaladar (restaurant) owners share their passions and stories of how they launched their businesses ⢠Meander through lively plazas and side streets and engage with community projects ⢠Weāre treated to a performance by the young Habana CompĆ”s dance group ⢠Stroll through a market, with a chance to test your bargaining skills.



Nights 3-5
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 Departmentās Office of Foreign Assets Control (OFAC) under a category called āSupport for the Cuban People.ā 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 deviationāespecially 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 āSupport for the Cuban People.ā 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 Cubaās 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 usāand bike like a Cuban!
When traveling abroad, things donāt 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 regionāitās all part of the adventure!
In Cuba weāre prohibited by the US State Department to support government-affiliated businesses, which include nearly all hotels in the country. To respect this requirement, we stay in privately owned and operated casas particulares, a uniquely Cuban form of accommodation in which locals open up rooms in their homes to welcome visitors.
While some casas particulares in Havana are practically indistinguishable from boutique hotels, those in the Cuban countryside are a rustic and local experience a far cry from our usual accommodations. The blackouts and fuel shortages which are the Cuban norm mean the very real possibility of periods without air-conditioning or hot water (though all our casas particulares are equipped with these amenities). While we hope you enjoy this behind-the-scenes immersion into Cuban life, we acknowledge that in order to do so you'll need patience, flexibility and appropriate expectations.
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
This rural guest house experience welcomes us into a collection of private Cuban residences with basic amenities such as ensuite bathrooms and air-conditioningāa hybrid somewhere between a homestay and a casual B&B unique to traveling in Cuba.
Nights 3-5
*Deluxe Hotel
An elegantly restored boutique oasis in Havana's modern and well-to-do Vedado neighborhood.
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Bikes
Choose Your Perfect Bike
Our bikes are designed and built with specific cyclists and riding styles in mind, so we can always offer you a perfect ride. Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Included in your trip price
- Suited for a wide range of cyclists
- Comfortable ergonomic seat
- Long wheel base adds to the bike's control and stability
- Upright handlebars only
Review Snapshot
by PowerReviews
Reviewed by 6 customers
Excellent learning experience
The leaders Mikra, Edwin and the support staff took care of all our needs and made the trip very enjoyable. This trip was very educational and things were what I expected and others, mainly the people, were thankful that we were visiting Cuba and seeing what it was really like. The biking and hiking was challenging with excellent views. The leaders had a couple surprises that made the experience much better, I won't ruin the surprise.
An adventure into history and culture, the "Backroads way"
Backroads provided an experience in Cuba in a way only they can. We met wonderful people and learned about Cuban history and culture from the people themselves. The relationships our leaders have created with the Cuban people are genuine and sincere; which gave us a very unique insight into their lives and all of Cuba. The caves, hikes, towns and bike routes we experienced were all beautiful. It was a typically fantastic Backroads trip with the added enjoyment of learning about a piece of recent, important world history.

Perfectly planned - amazing experience all around!
Verified Buyer
From the pre-departure details to the accommodations, dining, transportation, activities, surprises and amazing Cubans we were introduced to.... Backroads exceeded all expectations!


Backroads was fantastic and I would highly recommend it
Verified Buyer
Backroads was fantastic and I would highly recommend it to friends & family. Every moment was well-thought out and well executed
Wonderful Cuba
Verified Buyer
The Cuba trip was great. Toured caves, met with Cuban baseball players, young children studying music and dance, interesting art studios, biking with former members of Cuban baseball team who were generous with their time and support. All truly made for a memorable trip, almost forgot the rides in the old cars in Havana. What fun!
CUBA IS AMAZING
SO DIFFERENT OF EVERYTHING WE HEAR ABOUT AND BACKROADS LEADER WONDERFULL AS ALWAYS.
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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