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.