For most of us, a cycling holiday takes a lot of planning: Where are the best roads? Do I rent a bike or take my own? What will the weather be like? We spoke to the co-founder of a cycling tour company to ask him where his bucket-list rides were. We said forget the logistics. If you could ride anywhere in the world, purely for the love of the ride, the landscape, and the adventure, where would you go? Here’s what he had to say.
For Damian Hancock, co-founder of boutique Italian cycling tour company A’qto, whether he’s developing a ride for himself or creating a tour itinerary for A’qto, the overarching principle is always the same: how can I create the perfect day, day after day?
“Whenever I dream about where I’d ride next, it’s always a similar combination,” says Damian. “A challenging route, usually with mountains or hills to climb, a stunning landscape and then the final reward of the day, an immersive local food, wine and cultural experience of the region.”
Because for Damian, it’s never just about elevation or speed. Each destination is chosen not just for the physical challenge, but for the sensory one – the kind that stretches your perspective, not just your muscles.
“There’s a saying in Italy, ‘chi va piano, va lontano,’” he says. “‘He who goes slowly, goes far.’ It’s true on the bike and in life.”
Here Damian shares his top-five journeys on his bike bucket-list to complement his daily rides wound through the switchbacks of the Italian Alps and the sun-drenched hills of Sicily. And while he rides for a living, leading immersive cycling tours through some of Italy’s most beautiful regions, he’s still, at heart, a dreamer on two wheels. Because no matter how many peaks you’ve climbed or piazzas you’ve coasted into, there’s always another mountain calling, just for the joy of the ride.
1. Scottish Highlands, Scotland
For the rugged beauty, post-ride pints, and windswept solitude.
“Scotland draws me in for the drama of the land,” says Damian. “The wild, expansive highlands, the sense of isolation, and the slow roll into a village pub at the end of the day.”
Think quiet, narrow roads winding between lochs and peaks, where sheep outnumber cars and the air smells of peat and sea spray. The climbs are short but with sharp pinches, and the pay-off is always worth it, especially when it ends with a dram of local whisky by a fire. It’s the kind of ride that doesn’t just test your legs, but fills your spirit.
2. Copper Canyon, Mexico
For the raw challenge, gritty gravel, and spicy, flavoursome post-ride meals.
Imagine the Grand Canyon multiplied by four and threaded with remote dirt roads. That’s Copper Canyon. “This one’s for the pure challenge,” says Damian. “It’s tough riding on gravel, long distances, intense climbs, but with incredible cultural richness and depth.”
Riding here would mean remote gravel roads and a genuine connection to the land and its people. Meals would be hearty and homemade, and evenings would be shared with locals, over tamales, tequila, and stories. “It’s not polished or predictable. That’s what makes it magical.”
3. The French Alps in Autumn
For Tour de France legends and golden vineyard views.
There’s a reason riders obsess over Alpe d’Huez, Col du Galibier, and Col de la Croix-de-Fer. These climbs are hallowed ground, etched into cycling history by decades of Tour de France battles. “It’s not just the physical feat,” Damian explains. “It’s riding these iconic French climbs made famous by cycling legends.”
In his off season, Damian would spend a long weekend based in a tiny French village at the edge of the Rhone Valley, riding iconic cols in the crisp autumn air, and returning each afternoon for rustic meals and local wine tastings. “Autumn is when the crowds are gone, the leaves turn gold, and there’s a deep quiet.”
4. Hawai’i (Big Island)
For volcanoes, sea-level climbs, and elemental beauty.
Hawai’i might not be the first place that comes to mind for a cycling adventure, but for Damian, it’s the dramatic contrasts that make it so compelling. “The idea of starting at sea level and climbing over 3,300 metres up Mauna Kea, through the beautifully stark and desolate landscape of Hawai’i Volcanoes National Park, that’s what draws me in,” he says.
It’s a ride that begins beside the ocean and ends above the clouds, moving through black lava fields, misty rainforest, and raw volcanic terrain. Then, to balance the intensity of the climb, Damian would switch gears entirely and sea kayak the island’s crystal-clear waters, diving in for a swim, and ending the day with a simple, whole grilled fish by the water’s edge.
“It’s the combination of extremes, from summit to sea, that makes it unforgettable.”
5. Abruzzo, Italy
For forgotten mountains, quiet climbs, and rustic indulgence.
Of course, Italy had to make the list. But rather than the amazing roads of Tuscany or the Dolomites which Damian rides as part of A’qto tours, Damian’s pick is the underrated Abruzzo region.
“It’s one of Italy’s best-kept secrets,” he says. “The central Apennines are wild and steeped in history, with quiet climbs like Blockhaus, Campo Imperatore, Passo Lanciano, Prati di Tivo, and Vado di Sole, and villages where time seems to stand still.”
Riding here means encountering more goats than tourists, long climbs through beech forests, and hearty mountain fare like arrosticini, wild boar ragù, and handmade pasta such as maccheroni alla chitarra, all shared with locals who treat you like family.
Bonus – Dream Ride Already Ticked off the Bucket List: L’Eroica, Tuscany
Vintage bikes, woollen jerseys, gravel roads, and a piazza party.
One dream ride Damian has already experienced and returned to a whopping ten times, is L’Eroica, the iconic vintage bike ride in Gaiole in Chianti, Tuscany.
“It’s 8,000 like-minded cyclists from across the globe, who are happy and friendly, with a great sense of camaraderie,” he says. “We ride pre-1987 steel bikes on Tuscan gravel roads in woollen jerseys.”
At the end of the ride, a beautiful party spills into the piazza, complete with food, music, and celebration. “After completing 10 editions, I truly believe it’s the best ride of the year, every year. It brings together challenge, reward and connection – the perfect cycling experience.”
The Essentials: Packing and Preparing for a Dream Ride
When asked what he never leaves behind, Damian is quick to answer: preparation.
“Of course packing is important, I always make sure I’ve got the right gear for the conditions, especially spare cleats and derailleur hangers, and the right kit for cold and wet weather, even in summer. But training is the most important thing.”
He varies his approach. “Sometimes it’s a gradual build, sometimes it’s a block of back-to-back rides, but the goal is always the same: to be physically and mentally ready for the ride. For the kind of riding we do in Italy, there’s a point where it’s going to hurt. You can choose whether that discomfort happens at home during your training, or mid-tour when you’re trying to enjoy the experience.”
His advice? “Train beforehand, even if it’s tough, that way you’ll have the energy to look up, soak in the scenery, and enjoy everything off the bike too.”
If you’re dreaming of your next great ride, Damian’s advice is simple:
Choose challenge. Choose culture. Choose connection.
“Don’t just look at the distance or elevation. Think about the whole experience. What will the food be like? Who will you meet? Will you be moved by the landscape?”
Because the best rides, he says, aren’t just measured in kilometres, they’re measured in moments.
