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Group of cyclists celebrate in Havana, smiling and holding a Cuban flag.

Cycle Cuba 2023

Challenge level: 4 out of 5

When can I go?

5 May - 12 May 2023 On Sale
Duration 8 days

What does it cost?

Registration fee (payable today) Info $598
Remaining amount
Total commitment Info

Cycle Cuba 2023

Live the Caribbean dream on this exquisite cycling challenge around its largest island. Together, we’ll explore every part of Cuba, from the turquoise coast to the lush Escambray Mountains.

Kicking off in Hershey, founded to produce chocolate for the US chocolate brand, our unbeatable route takes us up and down through time-warped towns and sugar plantations, citrus farms and forested mountains.

We’ll work up a sweat cycling through rolling countryside and share the road with the vintage traffic Cuba is renowned for. With stops in the old-fashioned town of Trinidad, Cienfuegos, widely known as the “Pearl of the South”, and at the stunning seaside resort of Varadero, we’ll get a feel for the culture and history, while experiencing the paradise we all dream about.

Don’t be fooled, this cycling challenge will be tough. Prepare for steep climbs and undulating terrain. Yet, every pedal will be beautiful, with vibrant green hills, palm trees lining the roads, and colourful colonial towns, full of Cuba’s iconic Classic Cars.

We'll finish our epic challenge at the Che Mausoleum in Santa Clara, with a Cuba Libre and a fantastic Celebration Meal.

Then, we'll head to Havana for an exclusive guided tour and a free morning to relax at the beach or explore the city.

Your itinerary

Day 1
UK – Havana

Our overseas challenge starts at the airport in London, where we meet as a group and catch our flight to the vibrant Caribbean island of Cuba. Stretching to a stunning 766 miles, Cuba is the largest island in the Caribbean and so the best to explore by bike!

Touching down in Havana in the evening, our local team greets us at the airport and we transfer to our hotel in the city to settle down for the night.

After time to freshen up, we enjoy a delicious Welcome Dinner and our local Challenge Leader gives us an exciting briefing for the charity bike ride ahead.


Day 2
Havana – Hershey – Matanzas – Varadero | approx. 56km

Waking to an early breakfast at our hotel, we transfer (approx. 1.5 hours) to the famous village of Hershey, founded by the chocolate tycoon Milton Hershey.

After WW1 disrupted the US sugar supply, Hershey constructed a sugar mill and built the town around it for his workers, plus one of Cuba’s only electric railway stations to transport his sugar all across the country.

Arriving in the Jardines de Hershey, we start our challenge with a bike fitting and set off on a short, uphill cycle over a quiet country lane to Comino.

After a short break, we undulate gently for approx. 28km through sleepy, agricultural villages and sugar cane farms. Then, we turn towards the hills and our challenge picks up.

The road grows steeper, and its surface becomes rougher with broken tarmac and potholes to watch out for. But this tough stretch is definitely worth the workout, as it rewards us with awesome views of the hills and gives us a fantastic first glimpse of Cuba’s old-fashioned traffic, with local farmers passing by on their ox-drawn carts. It’s a steady climb, but the lush vegetation and forest help to keep us cool in their shade.

We stop for a well-deserved picnic lunch. Then, it’s back on our bikes to follow the main road to Matanzas. The surface smoothens out again and we pass a rainbow of colourful, classic cars, as the traffic grows more intense. Upon reaching the city, we regroup and cycle together through the city centre and on to the beautiful Bay of Matanzas.

Cycling done for the day, we transfer by coach to our seaside accommodation in the paradise resort town of Varadero (approx. 45mins).

Day 3
Matanzas – Jaguey Grande – Cienfuegos | approx. 85km

Kicking off after breakfast at the hotel, we start the day cycling along the turquoise coast and across the Varadero bridge with panoramic views of the sparkling, Caribbean Sea. Our route then takes us inland towards the small country city of Cardenas, where Havana Club rum was founded in 1934.

It’s a bit early in the day to taste the local specialty, so we cycle on through the town and join the single lane Carretera Central road, once the main Havana to Santiago route.

Following the road for approx. 40km, we’ll see more vintage traffic, like Soviet tractors, colourful classic cars, horses and carts and other cyclists. Citrus, sugar cane and cattle farms stretch either side of us, enjoying the rich pastureland that had once boasted acres of sugar cane in the height of Cuba’s sugar trade.

Finally, we arrive at Finca Coincidencia, a stunning ecological farm with a ceramic studio owned by Hector Correa and his arty family, who spend their days growing tropical crops and making ceramics from the land’s clay.

We enjoy lunch surrounded by mango and guava trees and then jump back on our bikes for our final approx. 25km stretch to Jaguey Grande in the Zapata Peninsula.

This is where today’s ride ends, and we rest our legs on an approx. 1.5hrs bus transfer to Cienfuegos, aka. 'The Pearl of the South'. With a UNESCO World Heritage Site city centre, Cienfuegos owes its eclectic mix of architecture to the French migrants that founded the city in the 19th century.

If time permits, we may be treated to a short orientation tour of Cienfuegos, before we head to our hotel in the city and settle down for dinner and a good night’s rest.

Day 4
Cienfuegos – Trinidad | approx. 91km

After fuelling up with a big breakfast for one of our most challenging days, we cycle out of the city and into more pastureland. Our route takes us undulating through rolling hills for approx. 12km and then veers right onto the main road to Trinidad.

We now enjoy a spectacular ride along a smooth road lined with palm trees, the Escambray Mountains gazing down upon us from the left, while vibrant hills roll to our right.

The rest of the morning sees us conquering more hills, as we cycle up and down on smooth tarmac through the sublime countryside, stopping for refreshment breaks in the shade along the way.

After approx. 50km, we reach our lunch stop in the tiny village of La Vega, where we tuck into a tasty Cuban country lunch. Then, we're back in our saddles to ride the relatively flat final 30km to Trinidad.

We know we’re almost at today’s finish line when we encounter some short hills, which take us through the outskirts and into the World Heritage town of Trinidad.

A jewel of colonial architecture, Trinidad’s traditional methods of transport and cobbled streets give us a sense of entering a time warp. We cycle to our hotel and finally relax with dinner and a great night’s sleep!

Day 5
Trinidad – El Mirardor – Sancti Spiritus | approx. 71.8km

Waking to an early breakfast, we start the day with a short transfer to the centre of Trinidad for an exclusive guided walking tour. This gives us great insight into the history of the town, which was a centre of the sugar trade in the 18th and 19th centuries.

Our tour ends in the pretty square of Plaza Sant’Ana, where we board our bus for a short drive to El Mirador. Here, our bikes await, and we waste no more time gearing up and set off for today’s cycle through a scenic valley of sugar mills and tobacco fields.

We see the infamous Manaca Iznaga tower a while before we reach it and stop for a break to take in the striking landmark. Erected in 1750 and owned by one of Cuba’s wealthiest families, the 44m tower was used to watch over the slaves working in the sugar cane fields, its bell used to summon them.

From here, we continue along the undulating road past field after field of sugar cane and stop for a picnic lunch along the way. As on most of the days of our challenge, we enjoy fairly smooth tarmac under our tyres, but our road route gives us quite a bit of traffic to look out for.

At last, our day of undulations comes to an end at our hotel in Sancti Spiritus, another beautiful town with colourful colonial architecture. Now it’s time to tuck into dinner and kick back for a restful night, ahead of our final day’s cycle.

Day 6
Sancti Spiritus – Santa Clara | approx. 82km

Rise and shine to our last day in the saddle, and it’s a little easier than our past couple of rides. We leave Sancti Spiritus after breakfast and share the road with a bit of heavy traffic on the outskirts of the town.

This quietens as we reach the Carretera Central, once the main road of Cuba, but now mainly used by agricultural vehicles, like horses and carts, tractors, and bicycles. We pedal on through more sugar cane plantations and sleepy, rural towns, tackling plenty of gentle undulations, much easier than the hills we’ve faced on other days.

This works us up an appetite for our final picnic lunch and then we continue following the road to Santa Clara. When we reach the outskirts of the city, we regroup and cycle our last stretch together through the centre as a peloton, with a spectacular finish at the Che Guevara Mausoleum.

Here, we toast our success with a Cuba Libre and take the opportunity to visit the Mausoleum, before de-fitting the bikes and transferring to our hotel for dinner.

Day 7
Santa Clara – Havana

We bid goodbye to Santa Clara after breakfast on a relaxing drive to Cuba’s amazing capital city of Havana.

Here, we’re treated to a brilliant guided tour of the city, including a walking tour of the old town and Revolution Square (Plaza de la Revolución). Dominated by the 109m memorial of the national hero, José Marti, the square has hosted many important political rallies and masses from the pope.

Heads full of fascinating political and historical insight, we check into our hotel and have free time to freshen up and relax. Tonight, we reunite and revel in our achievement some more with a mojito and a special Celebration Dinner with live music to entertain us.

Day 8
Havana – UK

This morning is free for you to spend as you please, relaxing at the hotel or exploring Havana. Breakfast is included, but lunch isn’t, so please make your arrangements and take your pick of the city’s many exquisite eating establishments.

You may want to visit the famous Museum of the Revolution (entrance not included) or take a stroll down the Malecon, the city’s broad sea wall, to make the most of the incredible views across the Caribbean Sea.

We meet back up at midday to check out of the hotel and transfer to the airport for our flight back to the UK. Touching down in London in the late evening, we part ways, and you make your way home, ready to book your next Dream Challenge.

Book my place

Funding options

Self Funded

Pay the registration fee (£399) and challenge costs (£1,995) + airport taxes/fuel surcharge (capped at £475).


Pay the balance.

  • Pay a non-refundable registration fee of £399 when you book, which is used to administer the challenge and secure your seats with the airline.
  • Pay your challenge cost of £1,995 yourself 12 weeks before the challenge starts.
  • The challenge costs cover flights (excluding airport taxes and the fuel surcharge, approx. £475) your food, accommodation, a guided walking tour of Havana, bike hire and mechanical support, all transfers and luggage transportation in Cuba, entry fees, your Cuban Tourist card (£20), outdoor remote first-aid trained challenge guides and medical support, including a UK doctor with expedition medicine training.
  • Choose to fundraise as much as you can or make a personal donation to the charity of your choice.
  • Please also remember to budget for your airport taxes and fuel surcharge (capped at £475).
Book my place


Pay the registration fee (£399) and airport taxes/fuel surcharge (capped at £475), and fundraise £3,990 or more for your chosen charity.


Minimum sponsorship target

  • Pay a non-refundable registration fee of £399 when you book, which is used to administer the challenge and secure your seats with the airline.
  • Fundraise the minimum sponsorship target of £3,990 for a charity, hospice or animal sanctuary of your choice at least 12 weeks before your challenge starts.
  • Providing you have raised the funds, the charity you are supporting will pay the challenge costs of £1,995 on your behalf.
  • The challenge costs cover flights (excluding airport taxes and the fuel surcharge, capped at £475) your food, accommodation, a guided walking tour of Havana, bike hire and mechanical support, all transfers and luggage transportation in Cuba, entry fees, your Cuban Tourist card (£20), outdoor remote first-aid trained challenge guides and medical support, including a UK doctor with expedition medicine training.
  • Please also remember to budget for your airport taxes and fuel surcharge (capped at £475).
  • Please note that not all charities are happy to commit to the minimum sponsorship option. If you choose this option, we contact the charity you want to support on your behalf. If they are not happy with the minimum sponsorship option, we’ll let you know as soon as possible.
Book my place

Cycle Cuba 2023

This charity bike ride is not designed for Olympic athletes – it is designed for people looking for an amazing overseas challenge to train and get fit for. A number of the people who will take part in this challenge will have a low level of fitness when they sign up.

We'll cycle up many steep hills in humid conditions, so we strongly recommend you train, and please try to incorporate hills in your training rides. Once you sign up, we'll send you a cycling training plan, which builds up over time and will set you up for success. Remember, the more you train, the more you'll enjoy the real deal!

This adventure is the perfect motivation to get fit, gain amazing insight into the culture and history of Cuba, and raise vital funds for charity.

Please don't be! The majority of people will sign up on their own. Our charity challenges are renowned for the amazing camaraderie and lifelong friendships made as our groups conquer these incredible feats together.

Once you've signed up for the challenge, we'll send you a link to a private Facebook group for everyone registered for Cycle Cuba 2023. Please use this space to swap questions, advice and updates with your fellow cyclists on your training and fundraising.

You may also want to see if any of your fellow participants would like to train and fundraise with you.

You need to be 18 years old or over to take part in Cycle Cuba 2023. There's no maximum age limit. One of the amazing things about this challenge is that it brings adults of all ages and from all cycles of life together for one amazing charity event.

16 and 17-year olds may participate if given permission by Dream Challenges. Please get in touch with us to discuss this. Simply email bookings@dream-challenges.com or call us on 01590 646410 at least 17 weeks before the challenge and we'll be happy to help.

Your non-refundable registration fee of £399 per person is used to secure your seats with the airline and secure rooms at the top-rated, luxury hotels we stay in throughout.

Your challenge costs of £1,995 cover:

  • Your flights (not including airport taxes and the fuel surcharge, capped at £475)
  • Meals throughout the challenge, except for your lunch and dinner on Day 8 in Havana
  • Accommodation*
  • Bike hire
  • All transfers and luggage transportation in Cuba
  • Cuba Tourist Card to enter Cuba**
  • Entry fees where applicable
  • A team of fantastic, outdoor remote first aid-trained local guides and Dream Challenges staff
  • Full support from the Dream Challenges office in the lead-up to and during your challenge
  • Medical support, including a UK doctor with expedition medicine training, who will accompany us throughout the challenge
  • Mechanical support
  • Your Cycle Cuba 2023 medal and t-shirt

*Accommodation is included on a twin-sharing basis. If you would rather pay for a single supplement and have a room to yourself, please get in touch with us at bookings@dream-challenges.com or on 01590 646410 (Mon - Fri, 9am - 5pm) at least 17 weeks before the challenge and we can arrange this for you for an additional cost.

**All participants will need a Cuban Tourist Card to enter Cuba and this is included in your challenge costs, provided you are a British or European passport holder. If you aren't, please get in touch using the details above.

A cycle helmet is essential and must be worn at all times. Cycling shorts are also recommended, and everyone will need their water bottles or a CamelBak-type hydration system.

Apart from that, no specialist equipment is required. We will supply you with a list of everything you will need to take before you go.

Cyclists will have the use of 18 or 21-gear bikes, and we suggest you bring the saddle or gel cover you are used to riding on.

In addition to paying your registration fee (£399) and either self funding your challenge costs (£1,995) or fundraising the minimum sponsorship target (£3,990), you'll need to budget for your:

  • Airport taxes and fuel surcharge (capped at £475)
  • Travel to and from the airport in the UK
  • Personal travel insurance
  • Gratuities
  • Personal expenses
  • Your lunch and dinner on Day 8
  • You may also choose to pay for a single supplement and have a room to yourself.

The Dream Challenges team will support you throughout your charity challenge, from the moment you register until the weeks after you return. We are always on hand to answer any questions that you may have about your training or the bike ride itself.

Once you have registered, we will send you a Welcome Pack with everything you need to know about your cycle in Cuba, including the itinerary, an example insurance policy, details about our destination and the weather we can expect on our cycle, the structure of an average cycling day, a full kit list, and a realistic training plan. The training programme builds up gradually as the challenge gets closer.

We'll also send you regular updates in the lead-up to departure, with important details and seasonal fundraising ideas. During the cycle, we'll have a UK doctor with expedition medicine training accompanying the group at all times, along with a team of outdoor remote first-aid trained challenge guides.

We will stay in comfortable hotels throughout the challenge.

Accommodation is included on a twin-sharing basis. However, if you would rather have a room to yourself, please get in touch with us at least 17 weeks before departure and we can arrange a single supplement for you at an additional price. You can call us at 01590 646410 during our office hours (9 am-5 pm, Monday-Friday) or email us at bookings@dream-challenges.com 

We will cycle mostly on road throughout our charity bike ride in Cuba. These will vary from well-surfaced roads through towns, the mountains and the countryside to rougher roads with potholes, and rural lanes.

We will also tackle steep climbs, so please try to include hills in your challenge training. Don't let the hills deter you, though - the breathtaking views across Cuba will be more than worth the climbs!

There will be around 30-35 participants in our group for Cycle Cuba. You will no doubt make loads of new friends.

Travel Insurance
You will need to take out your own personal travel insurance upon registering for this challenge, covering health, accident, loss and repatriation. We advise you to arrange personal travel insurance as soon as possible after you register to ensure you have coverage for your booking as well as the cycling challenge itself.

In your Welcome Pack, you will receive information about an insurance provider that specialises in our type of challenges and also covers you for cancellation due to medically-diagnosed COVID-19. You can, however, take arrange insurance with another provider, as long as it covers you for a charity bike ride in Cuba.

Please ask the insurer about the nature of the cover. It is your responsibility to ensure you have adequate cover for your challenge.

All participants will need a Cuban Tourist Card to enter Cuba. This is included in your challenge costs, provided you are a British or European passport holder. We will send you all the details closer to the challenge.

If you are not a British or European passport holder, please get in touch at bookings@dream-challenges.com or on 01590 646410 (Monday-Friday, 9 am-5 pm), and we can discuss your travel card arrangements.

We’ll have a UK doctor with expedition medicine training, who will be with you throughout the whole challenge in Cuba. We'll also have a team of outdoor remote first aid trained challenge guides and a local cycling challenge leader, who knows the area like the back of their hand.

No, your main luggage will be transported in vehicles each day by our support team. We advise you to pack light.

You will need a bag to go on your bike or a waist bag for things like your water bottle (ideally at least 2 litres) and phone/camera, along with any other personal items you want to have on hand.

Any extra items you may need during the cycling day can be carried in the support vehicle, which you will have access to at the snack stops and lunch.

Yes of course! If you wish to extend your stay in Cuba, please let us know at least 17 weeks before our departure date and we can arrange this for you.

You can email us at bookings@dream-challenges.com or call us on 01590 646410 (9 am - 5 pm Monday-Friday).

As we're not medically trained, we're afraid we can't offer you advice on this. We recommend you contact your GP or your local travel clinic, who will have the latest travel health advice.

We also recommend you visit the NHS Fit for Travel website here, to keep up to date with current travel health news and advice on staying healthy abroad.

NHS Fit for Travel website: https://www.fitfortravel.nhs.uk/home

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