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*Includes bike rental*
Buzzing and indescribable Havana
The famous tobacco region of Viñales
Boat ride across beautiful Lake Hanabanilla
Ride the coastal highway from Trinidad
Snorkel in secluded beach cove
Stay in hotels and locals’ homes
Pedal through the Las Terrazas eco-village
Visit the Che Guevara Mausoleum
Legal for Americans as a People to People experience

8 Days – $2,499

Mixed Riding Tour

Dates (Sat > Sat):
October 7 – 14
November 11 – 18
December 9 – 16
January 20 – 27
February 17 – 24
April 21 – 28

*Private groups of 6 or more select their own dates*

11 Days – $3,099

Mixed Riding Tour

Dates (Sat > Tues):
October 7 – 17
November 11 – 21
December 9 – 19
January 20 – 30
February 17 – 27
April 21 – May 1

*Private groups of 6 or more select their own dates*

Guaranteed Departures

No more worrying about whether or not a trip will run due to group size. If you book, you go.

Traveling as an American citizen? It’s still legal.

We’ve got you covered. Learn more about what makes this trip compliant with the requirements for a “People-to-People” license and what you need to know to travel to Cuba as an American.

Daily Itinerary

Live music on every street corner, famously empty roads, and a culture that doesn’t sit still. Ride along stunning beaches and into the mountains of the revolution itself. Seeing Cuba any other way is simply not seeing Cuba.

*In order to qualify as a People-to-People experience, this itinerary features a lot of daily cultural activities.*

Days 1 & 2: Arrival to Havana

¡Welcome to vibrant and buzzing Havana! Once everyone gets to Havana, we’ll go out for dinner and orientation, followed by an evening stroll through Old Havana. The next day we take a ferry out to east Havana for our first ride. An evening cruise in classic American cars is a great way to end the day.

Day 3: Hanabanilla

After a transfer to Santa Marta, we’ll prep the bikes while you get a guided tour of the famous Che Guevara mausoleum. Then, a beautiful rolling ride to Lake Hanabanilla. Take a dip to cool off after what is definitely a highlight cycling stage.

Day 4: Trinidad

After a boat ride across the lake, we come down from the mountains and head to the incredibly well-preserved city of Trinidad, a UNESCO World Heritage Site. Coastline on one side, big green mountains on the other.

Day 5: Guajimico

Nothing more than a tiny fishing village, Guajimico has become one of our favorite stops of the entire trip. Individual cabinas, an amazing pool overlooking the bay, and a private boat ride to do some snorkeling. This place is pretty special.

Day 6: Playa Larga

Today we get off the main highways and ride along a quiet unpaved road through farms and fishing communities. Our lunch stop is impossible to beat: a local family cooks us fresh seafood over an open fire. And it is every bit as good as it sounds. Then on to the famous Bay of Pigs where we stay for the night.

Day 7: Soroa

Tonight we stay in an intentional eco-village where locals have teamed up to protect their UNESCO Biosphere Reserve status. A fantastic twilight ride takes us along rolling hills and into the forested area known for its coffee. *We arrange a shuttle for the 8-day riders to transfer back to Havana so they can fly out the following day.

Days 8 & 9: Viñales

The Viñales Valley is a special place with lots of options for activities. Home to some of the best tobacco farms in the world, we’ll visit one and learn about the importance of the crop in Cuba. An extra day for exploring nearby caves, rock climbing, or riding along quiet back roads. An early start on day 10 gets us back to Havana with time to enjoy our final night.

Day 10: Havana

Our final ride take us up to the classic town of Sumidero where locals hang out in the park playing dominoes and offer to take pictures with us. A wonderful family prepares us lunch on their farm before transferring back to Havana. A final dinner and of course, a night out to celebrate the end of a great trip.

Day 11: Departure from Havana

¡Hasta luego! If you’ve got time before your flight you can head back to Old Havana or stroll along the malecon seawall. Either way, we’ve organized your shuttle to the airport.

315 Total Cycling Miles (210 for 8-Day)

Avg. miles/day 35
Cycling days (6 for 8-day) 9
% Paved Roads 80
% Unpaved Roads 20

Empty highways and obsessively scouted routes make the cycling for this trip hard to beat. Feel free to rent one of our quality hardtail mountain bikes (Cannondale, Trek, and Haro) or bring your own. Regardless, the support vehicle carries luggage and gear…or you in case you decide to skip a certain section. Terrain is roughly 3/4 paved and 1/4 non-technical off road.

Everything from rustic riverside cabins to classic hotels. Not to mention, casas particulares – Cuban families open their homes to guests all over the country and we’ve selected the best of the best. Rooms are booked as double occupancy but you can pay extra for an individual room at checkout.

We take advantage of the best restaurants in each city and provide some excellent roadside picnics to keep us fueled. Expect fresh seafood and vegetarian options throughout and of course, slow-roasted Cuban pork. Local lagers are cold and refreshing and the rum: legendary.

For all trips, Day 1 is the arrival date and the last day is the departure date. Please note that we do not book international flights.
Both 8-day and 11-day: Arrive HAV > Depart HAV


*Bike rental*
All accommodations
All in-country transportation, including airport transfers
All breakfasts, most lunches, and most dinners
Support vehicle w/snacks & water
Bilingual guide and professional mechanic
Entrance to Cueva del Indio
City tours of Havana & Trinidad
Cruise in classic American cars
Boat ride across Lake Hanabanilla
Tobacco farm tour w/cigar sampling
Private boat trip + snorkeling with local captain

Not Included

Airfare to/from Cuba
Travel/medical insurance (required)
Trip cancellation insurance (recommended)
Single supplement for individual rooms ($300)
Tips for guides

Difficulty Level: Moderate – Challenging

Although there aren’t any massive mountains in Cuba, we do ride through some hilly parts of the country so coming prepared will definitely help. We make regular water/fruit stops and the support vehicle allows us to accommodate a very wide range of speeds. Want more info? Contact us and we’ll send you the elevation profiles for each day.

Questions? Let’s talk it out…

Feeling like you need to talk to someone before booking? Never done anything like this before? Worried about flights or just curious to hear more about our approach to designing trips?

Call or email with ANY question and we’ll gladly help. Seriously, there’s a lot going on here so don’t hesitate.

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