Cycle Cuba

10 days


6 days





2025 & 2026

Explore the Pearl of the Caribbean by bike

An action packed cycle challenge exploring Cuba’s lush green countryside, colonial towns and revolutionary history. Experience the vibrant culture and stunning landscapes of Cuba on this unique cycling adventure. Highlights include exploring Havana, cycling through the Escambray mountains, visiting the Che Guevara Mausoleum, and relaxing on Santa Maria Island.

The Challenge

Cycle across captivating cuba

Embark on an unforgettable cycling adventure through the heart of Cuba, where vibrant culture, breathtaking landscapes, and rich history await. Start your journey in the iconic city of Havana, then cycle through picturesque towns, lush forests, and rolling farmlands. Experience the thrill of riding through the Escambray mountains, with stunning views and challenging climbs that reward your efforts. Visit the historic Che Guevara Mausoleum in Santa Clara, and enjoy the serene beauty of Lake Hanabanilla. Finally, relax on the pristine beaches of Santa Maria Island, soaking in the Caribbean sun.

Throughout the trip, enjoy top-notch service, comfortable accommodations, and delicious Cuban cuisine. Our expert guides will ensure your safety and provide fascinating insights into Cuba’s culture and history. This unique cycling adventure offers a perfect blend of physical challenge and cultural immersion, making it an ideal way to explore the diverse and enchanting island of Cuba.

The Experience

Life on the Cycle

On an Action Challenge trip, you’ll be part of a team which takes on an adventure together – and that’s what makes the experience so special. Getting to know others, supporting each other when the going gets tough, laughing together & the new friendships that will stay with you for many years. Led by a UK Leader and supported by a Medic overseeing the group’s wellbeing – you’ll be in safe hands, and our expert local logistics team & guides will ensure it all runs like clockwork. These are ‘fully inclusive’ trips – leaving you to focus on your challenge and enjoy it!

An Action Challenge trip is much more than a holiday! It brings like-minded people together in fantastic landscapes, provides the best support, and enables the group to take on a tough & unforgettable challenge which forges new friendships, broadens horizons, and leaves you wanting more of life’s adventures!

The blueprint for the Action Challenge trip is based on delivering a high-quality enjoyable experience – and doing it all safely. An experienced UK Leader, ensures that all aspects of the challenge run to plan – and one of our UK Medics with an expedition med kit is on hand to look after the group’s wellbeing – enabling everyone to have the best chance of completing their challenge.

We go to great lengths to ensure that we only use the best local organisations to supply the all-important ground logistics and the on-challenge support, catering, and hospitality teams – with experienced guides leading the way on the trails guided by their deep local knowledge and authentic style.

We appeal to like-minded people with a similar sense of adventure – but often from very different backgrounds, and with a wide range of experience, ages, levels of fitness, and personal ambitions. Our trips are perfect for individuals, couples, and small groups of friends to join –to take on a unique challenge as part of a larger group which shapes & bonds as the adventure unfolds!

Whether it’s the hotels, restaurants & transfers before & after the main challenge – or the challenge accommodation & meals whilst out on the trails – our all-inclusive packages mean that you will get a top-quality experience at a great value price! Flights are generally included, but there’s a ‘land only’ option if you’d prefer to book your own – and single supplement accommodation upgrades are available.

Visas- You must organise your tourist card yourself prior to arrival in Cuba. Advice on how to apply for this will be provided to you once booked onto the challenge in the App. 

The group comes together – takes on a tough challenge together – and then celebrates its achievements in style on the final night of the trip in a local restaurant or hotel, with medals, awards, and a bit of a party! Many of our participants make new special friends on our trips – and quite a few come back together for another challenge in the following years!

A successful challenge starts with good preparation. The better prepared you are the more confident you’ll be, and the more you’ll enjoy it! Our ‘Challenge App’ will have all the info & details of what to expect on your challenge – and how to prepare for it – and we have optional training walks, training weekends, and a 50km place on one of our UK Ultra Challenge events to get out on the trails and test your fitness, kit, & equipment.

Itinerary & Route

Please note that some details of the itinerary may change, you will be provided with a detailed itinerary once you are signed up to the challenge.

We depart London for a day flight to Havana and transfer directly to our comfortable central hotel in Old Havana.   


Meals: D inflight Accom: Hotel

This morning, we visit the cultural and historical heart of old Havana before we have an early lunch and then transfer 3hrs to Playa Larga on the south coast by the Bay of Pigs. This is stunning with beautiful beaches and a relaxed atmosphere. It was here that the CIA-backed invasion of Cuba landed in 1961 and led to the humiliating failure. As the sun sets, we will have a bike fitting and briefing on the challenge with the full team, before sitting down to a welcome dinner and beer overlooking the Caribbean.

Meals: B, L, D Accom: Hotel

We will wake early for breakfast to make the most of the cooler morning, as we have a long tough ride on mostly flat roads for our first cycling day. We then head northeast through rural areas, arriving for lunch in Rodas. This afternoon, we will head south past the Damuji Lake, Ariza and El Salata villages and rolling farmland, to end the day at the UNESCO town of Cienfuegos. We have a chance to discover its incredible colonial centre before relaxing back at our hotel. This evening will conclude with an evening meal before getting some much-needed rest.

Meals: B, L, D   Accom: Hotel

Today brings no relief to the legs, as we begin with a short stretch of hills after breakfast. Once over this rollercoaster of a ride, the rest of the day is flat roads in rural settings with nature all around us. At midday, we will stop to enjoy some lunch and soak up the stunning landscape whilst we recuperate before we continue with our adventure into the afternoon. We will then ride into the World Heritage town of Trinidad, famous for its summer carnivals when the city explodes to the sound of salsa and meringue. Our ride ends on the coast at Playa Ancon, where we are once again cooled by the sea breeze and sit with our feet up after a good day’s ride, watching the sunset with a classic Cuban cocktail and evening meal.

Meals: B, L, D   Accom: Hotel

Today is one of the highlights of the challenge, especially for those who love the hills. As we head north out of Trinidad after breakfast, we are soon in the cooler climates of the Escambray mountains. This area is covered in good tropical forest and the hills should have us fighting for breath as we tackle the tough climb to the lookout point at 500m. At a suitable point along the route, we will stop for some lunch and a rest. As we enter the afternoon, we will descend into the centre of the mountain range for lunch at Topes Des Collantes and then continue north to arrive at Jibacoa where we drop down to the port for a stunning ferry trip over Lake Hanabanilla. In the evening, we will then check into our hotel here, a great place to relax after a tough cycling day.

Meals: B, L, D   Accom: Hotel

Following breakfast, our day today is much easier as we start with a great 280m descent out of the Escambray mountains. The rest of the morning ride is through rolling farmland, but we should reach Santa Clara for lunch, a vibrant metropolis with lots of street life. This is yet another Cuban town that is great for people-watching and soaking up the atmosphere. This afternoon we visit the mausoleum of Che Guevara, the iconic rebel leader that fought so bravely against the American invasion, before going to our hotel to relax.


Meals: B, L, D   Accom: Hotel

Our final day of cycling is quite special as is the destination: the island of Santa Maria which is off the north coast of Cuba. Our route starts with 65km of good fast cycling to the town of Caibarien where we have lunch. This afternoon, we have 40km of riding on the incredible road that has been built into the sea, which takes us to the island of Santa Maria. Once at our hotel by mid-afternoon, we have time to relax and take in the scenery on one of the most beautiful beaches of the island. The perfect opportunity to rest our aching legs! Tonight, we will celebrate the end of our challenge in style.  Time to party!

Meals: B, L, D   Accom: Hotel

Today, after breakfast we will have a full free day at our resort hotel and on the beaches of Santa Maria.

Meals: B, L, D   Accom: Hotel

This morning, following breakfast, we will have an early transfer back to Havana and depending on our flight time we have free time to discover more of the city. We meet again later and transfer to the airport in time for our overnight flight back to the UK.


Meals: B

Landing back in the U.K. reflecting on the incredible memories you have made.

Costs & Fundraising

We’ve three payment & fundraising options for you to take on this challenge.

Self Funding

Sign up with a £395 online deposit & balance payment due 12 weeks before, with no fundraising target.

Fundraise for Charity

Sign up with a £395 online deposit & fundraise for a charity of your choice, with different target options.

Our Brochure

The Challenge brochure details the full itinerary, inclusions, and more – download for a full run down of the challenge details. 

Dates & Prices


Enquire with us below or if you want to speak to one of the team call on +44 (0)207 6695

About You
Trip Enquiry

How it works...


It’s like paying for an all-inclusive holiday.

You pay the registration deposit. The final balance for the trip cost will be due no later than 10 weeks before your departure date

If you want to fundraise for charity, you may still do this separately – either on or offline. All fundraising will be a direct donation to your chosen charity. Please contact them for more information.

How it works...


Take on one of our challenges and support a charity of your choice. You can choose how much of the trip cost you want to pay, and support your charity by fundraising the rest.

You pay the registration deposit, then fundraise double the remaining trip cost for a charity of your choice.

Action Challenge will invoice your charity for your final balance 12 weeks before departure.

You must complete 80% of your fundraising by 12 weeks before departure, with the remaining 20% completed 4 weeks after departure.

Let us know what charity you want to support when registering so that we can set up your challenge agreement.