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Classic Car in Havana in Cuba

The Caribbean Dream Cycle 2021

Challenge level: 4 out of 5

When can I go?

12 November - 20 November 2021 On Sale
Duration 9 days

What does it cost?

Registration fee (payable today) Info $75
Remaining amount
Total commitment Info

The Caribbean Dream Cycle 2021

The Challenge

Live the Caribbean dream on this exquisite cycling challenge around its largest island.

Kicking off in Havana, we’ll explore every part of Cuba, from the white-sand beaches and wildlife-packed wetlands to a time-warped town and the Escambray Mountains.

We’ll work up a sweat cycling through rolling countryside by day and freshen up by night at our luxury accommodation. Get ready to make cocktails, play dominoes, taste amazing Caribbean feasts and kick back at the beach after a day in the saddle!

With stops at the famous Bay of Pigs, the Plaza de la Revolución and the stunning Cienfuegos waterfront, 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. We’ll look out for hummingbirds and flamingos, take a dip in a serene mountain lake, ride alongside mango trees and gaze out across the sparkling Caribbean Sea.

As if our adventure couldn’t get any better, we finish with a classic car tour of Havana.

What's different about our Platinum Series Challenges?

You'll still conquer great distances, gain all the fitness benefits and donate to your favourite charity, but you'll relax in style. Travelling in small groups, you'll stay in top-rated hotels, board luxury vehicles for our transfers, relax with daily warm-up rubs and optional massages from a travelling physio. And that's not all... See all the perks of our Platinum Series challenges here.

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 magical 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 guide greets us at the airport and we transfer to our five-star hotel in the city to settle down for the night.

*You may also opt for our platinum door-to-door transfer service and we'll drive you from your doorstep to the airport in plenty of time for our departure. Simply get in touch and we can arrange this for you at an additional price.

 

Day 2
Havana | approx. 40km

We begin our day with a bike fitting and then set off on beautiful panoramic bike tour of Cuba’s capital city.

Taking in a fantastic array of areas, including Cubanacán, Siboney, Miramar, Parque Metropolitano de la Habana and Nuevo Vedado, we take a break at 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.

Hopping back on our bikes, we cycle through Vedado, past the Hotel Nacional, to visit the spectacular 1920s El Capitolio, Cuba’s National Capitol Building. We then continue down Prado Promenade, pass the remains of the Old City Wall and finally reach the impressive Arms Square.

After a delicious lunch at a restaurant in Old Havana, we cycle back to our hotel, admiring the brightly coloured Cuban cars as we go.

This afternoon, we have organised a complimentary massage for you to recover from the long flight. You then have free time to freshen up and relax, before heading out this evening for dinner and a cocktail making class at a fabulous Asian-Cuban fusion restaurant.

Day 3
Havana – Cienfuegos | approx. 70km

We leave our hotel early to transfer (approx. 2 hours) to the south of the island, we kick off in the Zapata Wetlands National Park, the largest wetlands in the Caribbean, declared a Biosphere Reserve by UNESCO in 2001.

Keep your eyes peeled for flamingos, manatees, the Cuban alligator and hummingbirds, plus a staggering range of plant-life, as we cycle to the Bay of Pigs. Infamous for the 1961 failed invasion by Cuban exiles, the Bay of Pigs may have a grizzly past, but the scenery is idyllic! We cycle alongside the sparkling Caribbean sea and past sleepy villages, stopping in a shady spot for lunch.

We finish our flat and fast day’s ride at Caleta Buena, a natural sea pool, where blue shores invite us for a swim. Of course, if you would rather stay dry, you can kick back on the waterfront with a cold beer.

From here, we transfer a short way 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. We find our charming hotel in the city and have a chance to freshen up for our dinner at the waterfront.

Day 4
Cienfuegos | 64km

After a big breakfast at our hotel, we cycle along the Trinidad Road past the city hospital and baseball stadium, to the serene outskirts of the city. Away from the hustle and bustle, our next 15km stretch takes us through the rolling Caribbean countryside, past colourful mango groves and lush, open fields.

We turn sharply and encounter several steep hills, which are murder for the thighs but Heaven for the eyes, as we enjoy exquisite views over the tropical vegetation.

Our challenging route evens out and we catch our breath cycling along a quiet country road lined with mango trees.

We pass Cienfuegos’ botanical gardens and a series of small villages and get a feel for the local lifestyle, before we come to today’s biggest climb. With unending idyllic vistas to encourage us, we ascend for the last few kilometres, tackle some steep sections and at last, reach the exquisite Hanabanilla Lake.

It may have been a tough cycle, but the views are more than worth it and we’ve saved the best until last. Tucked amidst the forested Escambray Mountains, Hanabanilla Lake (or Lago Hanabanilla) stretches over a breath-taking 26 square kilometres and snakes along the northern fringes of the Sierra del Escambray. Here, with views befitting of paradise, we enjoy our well-deserved lunch at a paladar.

We then return by bus to Cienfuegos and tonight, we tuck into a traditional Cuban feast of roast pork (veggie option available) and rum at Casa de Lily, with a game of dominoes to end the day.

Day 5
Cienfuegos – Trinidad | approx. 80km

Leaving our hotel after breakfast, we have another chance to take in some of the views we passed yesterday as we head out of the city and undulate through rolling fields.

Tackling a tough ten kilometres of hills, we veer 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 through the gorgeous Cuban countryside, stopping for refreshment breaks in the shade along the way.

We find our lunch stop in the small town 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 thirty kilometres 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 as we ride to our five-star hotel. Tonight, we dine in the town and kick back with rum and Cuban cigars.

Day 6
Trinidad – Varadero | approx. 80km

Rise and shine to our last day of cycling. After breakfast at our hotel, we bid Trinidad goodbye and transfer to our spectacular starting point, high in the Escambray Mountains.

From here, we cycle the sublime first half of our day’s ride, as we descend from enchanting pine forests into the tropical valley of Jibacoa. Along the way, we’re treated to views of beautiful waterfalls and can look out for all sorts of birdlife.

The scenery changes when we reach Jibacoa and gives us more fantastic insight into the local culture, as we undulate past palm trees, pretty, wooden cottages and small rural villages. As we approach Santa Clara, the road becomes busier, but it’s still a pleasant ride, with fields of sugar cane, tranquil rural towns and plenty of horses and carts to admire.

Stopping for a shady picnic lunch along the way, we press on up and down gentle hills, until we reach the outskirts of Santa Clara. Here, we regroup for our last stretch of cycling to our awesome finish line at the iconic Che Mausoleum, one of Cuba’s most important revolutionary monuments.

After an exquisite five days of cycling, we toast our success with a traditional Cubra Libre, de-fit our bikes and transfer to our hotel in Varadero. No doubt brimming with an epic sense of achievement, we tuck into dinner and enjoy a great night’s sleep at the stunning five-star hotel.

Day 7
Varadero – Havana

Today is free for you to spend as you please in the paradise resort town of Varadero. You can explore the local shops and pick up some souvenirs and/or kick back at the white-sand beach with a mojito or two!

Today, we also have the chance to explore the area further on a two-hour classic car tour, included in your challenge costs – the perfect way to end our Cuban adventure!

We then transfer back to our luxury hotel in Havana for a delicious dinner and our last night in the Caribbean.

Days 8 & 9
Havana – UK

Today after a final Cuban breakfast, we transfer to the airport and catch our overnight flight home.

Touching down in London on Day 9, we part ways and you make your own way home.

Again, you can opt for our platinum door-to-door transfer services and we'll drive you in our luxury coach right to your doorstep (not included in challenge costs).

Book my place

Funding options

Self Funded

Pay your registration fee and your challenge costs yourself.

$5,550

Pay the balance.

  • Your registration fee of £499 per person is used to secure your seats with the airline and to secure rooms at the luxury hotels we will stay at throughout.
  • Pay your challenge cost of £3,700 yourself 12 weeks before the challenge starts.
  • The challenge costs cover flights with a premium airline, including airport taxes and the fuel surcharge, your food, luxury accommodation, a Classic Car tour of Havana, high-spec bike hire and mechanical support, transfers in luxury transport, daily physio and massages, entry fees, pro cocktail-making class, guides, a bespoke cycling jersey, medal and medical support.
  • Choose to fundraise as much as you can or make a personal donation to the charity of your choice.
Book my place

FAQs
The Caribbean Dream Cycle 2021

You'll still conquer great distances, gain all the fitness benefits and donate to your favourite charity, but you'll relax in style.

Travelling in small groups, you'll stay in top-rated hotels, board luxury vehicles for our transfers, relax with daily warm-up rubs and optional massages from a travelling physio. And that's not all... See all the perks of our Platinum Series challenges here.

As we hope you know, the health and safety of our participants is always - and has always been - our highest priority.

Our team of experts here at Dream Challenges has created a brilliant 14-step initiative, to minimise the risk of coronavirus and maximise your safety. Please click here to see our ground-breaking plan and rest assured that you're safe booking with us.

If the challenge can’t happen on the planned date because of COVID-19, we would postpone the challenge until next year. We would, of course, let you know as soon as possible and give you the full details so that you can mark the date in your diary.

A challenge must meet the following criteria to go ahead:

  • The UK government, including the Foreign Commonwealth Office and the authorities of the destination country, must be allowing travel and events of this type at the time of departure.
  • There must be no general requirement for isolation or quarantine on arrival in the destination country or on the return to the UK at the time of departure.
  • The challenge must meet all the relevant parts of our 14-step COVID-19 action plan.
  • There must be enough participants wanting to travel to make the group viable.
  • The challenge must be an enjoyable and memorable experience within any actions that need to be taken.

The Dream Caribbean Cycle 2021 is not designed for Olympic athletes – it's designed for people looking for an amazing goal to train and get fit for.

A number of the people who take part on this challenge will have a low level of fitness when they sign up. Our cycle around the exotic island of Cuba is the perfect motivation to get fit and have the experience of your lifetime.

Once you have registered for the challenge, we'll send you a realistic and achievable training plan, which builds up gradually as the event gets closer. If you can't make it outside to train due to coronavirus restrictions, try out our ten fab indoor training ideas here

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 breath-taking views across the island will be more than worth the climbs!

You need to be 18 years old or over to take part in The Dream Caribbean Cycle 2021. 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 the event organisers. Please get in touch with us to discuss this. Simply email events@dream-challenges.com and we'll be happy to help.

Absolutely! As part of our amazing 14-step initiative to minimise the risk of coronavirus and maximise your safety on all our challenges, we're delighted to have found a fantastic travel insurance policy, which covers you for cancellation due to medically diagnosed COVID-19. 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 see the insurance policy here or click here to check out the full 14 actions we're taking to keep you safe.

Your non-refundable registration fee of £499 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 £3,700 cover:

  • Your economy flights on a premium airline, including airport taxes and the fuel surcharge, approx. £350*
  • Exquisite meals and snacks throughout the challenge with restaurant lunches (excluding free days, e.g. Day 7)
  • Accommodation at 4 to 5 star hotels*
  • All transfers in Cuba. This will be in luxury vehicles
  • High-spec bike hire
  • Cocktail making class in Havana on Day 2
  • Classic car tour of Havana on Day 7
  • Entry fees where required
  • A team of first-aid and COVID-19-trained challenge guides and Dream Challenges staff
  • Full support from the Dream Challenges office in the lead up to and during your challenge
  • Medical and mechanical support, including at least one UK doctor with expedition medicine training
  • Complimentary Travel Kits, including eco-friendly toiletries and sweet treats
  • Post-flight massage and daily warm-up rubs from our pro travelling physio in the mornings and at our lunch stops
  • Your Caribbean Dream Cycle 2021 medal and bespoke Scimitar cycling Jersey
  • Extra protocols taken to protect you from COVID-19 - please see our ground-breaking 14-step action plan here.

*Economy flights are included in the challenge costs. However, if you would like to upgrade to a business class or first class seat, please get in touch and we can arrange this for you at an additional price.

**Accommodation is included for all participants on a twin-sharing basis. If you would like to have a room to yourself, we can arrange a single supplement for you at an additional price. Please get in touch at least 14 weeks before our departure by emailing events@dream-challenges.com or calling 01590 646410 (Mon - Fri, 9am - 5pm).

A cycling helmet is essential. 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 pack before you go. Cyclists will have the use of high-specification 18 or 21-gear bikes and we recommend you bring the saddle or gel cover you are used to riding on, so you feel right at home on your bike.

Of course, if you're rather attached to your own, you're welcome to bring that instead. Please email us at events@dream-challenges.com if you would like to do this at least fourteen weeks before the challenge starts.

We'll also send all participants a free Travel Safety Kit ahead of the challenge and it's essential you bring this with you to minimise both your own and your fellow participants' risk of COVID-19.

Your Travel Safety Kit will include hand sanitiser, anti-bac wipes and face masks for each day of the challenge. Please note, you do not have to wear face masks while cycling.

In addition to paying your registration fee (£499) and your challenge costs (£3,700), you'll need to budget for your:

  • Tourist visa for Cuba (currently £25)
  • Travel to and from the airport in the UK. You can arrange this for yourself or book our fantastic platinum door-to-door transfers services. We'll drive you to and from the airport in our luxury vehicles.
  • Personal travel insurance.
  • Gratuities.
  • Personal expenses.
  • Your lunch on Day 7.
  • Economy seats with a premium airline are included in your challenge costs, but you may opt to upgrade to business/first class seats for an additional price. 

We will stay in stunning, four to five-star hotels throughout this platinum challenge.

Luxury 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.

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)

Our Dream Challenges are renowned for their camaraderie, but we find that the strongest bonds are formed in smaller groups. We'll travel in a group of around 20 people or fewer and you're likely to make friends for life! What's more, a small group means no queues!

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

We're delighted to have found a fantastic travel insurance policy, which covers you for this type of activity and also for cancellation due to medically diagnosed COVID-19. 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.

British passport holders require a tourist visa/travel card for Cuba. We will send you information and an application form to apply for your visa (currently £25 for British Citizens but subject to change).

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

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 free Travel Safety Kit, 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.

We will encounter all sorts of terrains as we cycle around Cuba, from smooth, well-surfaced roads through towns, mountains and the countryside to forest and coastal paths.

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 breath-taking views across the island will be more than worth the climbs!

Yes, you are welcome to bring your own bike, providing it is a mountain bike and suitable for the conditions. Please let us know if you would like to do this at least 14 weeks before the challenge starts and we can arrange this with the airline for you.

Yes, luxury 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.

Absolutely! We are delighted to offer all Platinum Series Challenge participants an optional door-to-door transport service for an additional price.

Instead of meeting at the airport in London, you can opt for us to drive you from your doorstep in luxury transport to the airport and drop you off at the end of our challenge as well. Please get in touch at least 14 weeks before departure to find out more and request this service for an additional price.

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