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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, the cycling will be tough, with steep climbs and undulating terrain, but 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. Finishing our epic challenge at the Che Mausoleum in Santa Clara, we’ll toast our success with a Cuba Libre and a fantastic Celebration Meal.

As if this adventure couldn’t get any better, we'll end with a guided tour of Havana and a free morning to explore the extraordinary city some more.

Your itinerary

Day 1
UK – Havana

Our adventure 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 some time to freshen up, we enjoy a delicious Welcome Dinner and our local Challenge Leader gives us an exciting briefing for the cycle ahead.


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

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

After WW1 disrupted the US sugar supply, Hershey took advantage of the gap in the market and constructed a sugar mill of his own, building 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 lush, overgrown 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 agriculture 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 famous 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 very well-deserved picnic lunch just before we hit the main road to Matanzas. Then it’s back on our bikes to follow the main road, where the traffic grows more intense and the surface smoothens out again. It may feel a little like cycling back in time as we climb past a rainbow of colourful, classic cars. Upon reaching Matanzas, we regroup and cycle together through the centre and on to today’s finishing point at 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 too 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. Lush fields stretch either side of us, full of citrus fruits, sugar cane and cattle, grazing on 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 of the lush 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 majestic Escambray Mountains gazing down upon us from the left, while vibrant, green hills roll to our right.

The rest of the morning sees us conquering yet 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 are 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 ride to our hotel and finally relax with dinner and no doubt 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 awesome guided walking tour. This gives us fantastic insight into the history of the town, which was once 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 Mirardor. Here, our bikes await, and we waste no more time to gear 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 you’ll be pleased to know 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 all the way 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 defitting 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 the 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 some 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 own arrangements – a brilliant opportunity to 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 for a midday 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 own way home, ready to book your next Dream Challenge.

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Funding options

Self Funded

Pay your registration fee and your challenge costs yourself.


Pay the balance.

  • Your registration fee of £399 per person is used to secure your seats with the airline and pay deposits to local suppliers.
  • 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. £350) 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 (approx. £350).
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Pay your registration fee and raise the minimum target for your chosen charity.


Minimum sponsorship target

  • Your registration fee of £399 per person is used to secure your seats with the airline and pay deposits to local suppliers.
  • 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, approx. £350) 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 (approx. £350).
  • 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.
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Cycle Cuba 2023

This cycle is not designed for Olympic athletes – it is designed for people looking for an amazing goal 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 will be tackling a lot of steep climbs and long cycling days on this challenge, so we strongly recommend you train. Once you sign up, we'll send you a fantastic 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 in one of the world's most incredible places is the perfect motivation to get fit, while raising vital funds for the heart charity or cardiac ward that means the most to you.

Please don't be! The majority of people will sign up on their own and our Dream Challenges are renowned for the amazing camaraderie and lifelong friendships made as our groups take on 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 feel free to use this space to swap questions, advice and updates with your fellow cyclists on your training and fundraising.

You may also want to reach out to the other participants in this group to see if there's anyone in your local area you can meet up to train and fundraise with.

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 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 events@dream-challenges.com 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, approx. £350).
  • 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 events@dream-challenges.com or on 01590 646410 (Mon - Fri, 9am - 5pm) at least 14 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 at events@dream-challenges.com or by calling us on 01590 646410 (Monday - Friday, 9am - 5pm) and we can discuss this.

A cycle helmet is essential and must be worn at all times. Cycling shorts are also recommended and everyone will need their own water bottles or a camel back-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 (approx. £350).
  • 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 is here to help you achieve your challenge and will support you all the way.

We are on hand from the minute you sign up to answer any questions that you may have about your training or the challenge itself.

Once you have registered, we will send you a realistic training programme to help you get fit for the challenge. The programme builds up gradually as the event gets closer.

During the cycle, we'll have a UK doctor with expedition medicine training accompanying the group from the get-go and at all times throughout the challenge, along with a team of experienced, 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 14 weeks before departure and we can arrange a single supplement for you at an additional price.

We will cycle mostly on road throughout this challenge and encounter well-surfaced roads through towns, mountains and the countryside to rougher roads with some potholes and rural lanes.

We will tackle quite a few hills on this challenge, including some steep sections, so please take this into account when training for the challenge. Don't let this deter you, though - the breathtaking views across the island will be more than worth the climbs!

There will be around 30-35 participants in our group on this challenge. You will no doubt make a group of fab new friends.

Travel Insurance
You will need to take out your own personal travel insurance covering health, accident, loss and repatriation.

Dream Challenges has a policy that provides appropriate cover for this type of activity and also covers you for cancellation due to medically diagnosed COVID-19. We will send you the details once you have registered.

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

You can, however, take out your own insurance providing it covers you for a charity cycle ride in Cuba.

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. 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 events@dream-challenges.com or by calling us on 01590 646410 (Monday - Friday, 9am - 5pm) and we can discuss your travel card arrangements.

We’ll have an event leader, plus a UK doctor with expedition medicine training, who will be with you the whole time. We'll also have a team of outdoor remote first aid trained challenge guides.

No, your main luggage will be transported 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 two litres) and phone/camera, along with any other personal items you want to have on hand.

Any extra items you may need during the day can be carried on 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, please let us know at least 14 weeks before our departure date and we can arrange this for you.

The easiest way to get in touch is by emailing us at events@dream-challenges.com or calling us on 01590 646410 (9am - 5pm 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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