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Three Friends Cycled Across Italy Through The Most Breathtaking Locations


Meet Jason Stirling and Dave Fletcher. Two friends from Melbourne, who started cycling together in college. Together, they’ve been on countless breathtaking bike adventures, from the highest road in the world in India, circumnavigating Iceland, Wales, France, Norway, Australia, New Zealand and most recently in Italy, cycling through Tuscany, the Amalfi Coast and the Dolomites. These are their words…

At that time it was really done as a form of procrastination, a good excuse to miss class, and soon enough it turned into a passion of ours. There’s something about a bike that gives you a sense of complete freedom. It’s such a simple machine but gives you the ability to explore such large distances, which makes it the perfect tool for travel. I also find the symbolism of the bike so perfect for life. It creates a sense of community, teamwork, adventure, freedom, simplicity and sustainability… all these beautiful qualities come out when you ride a bike, and that’s something I want to continue to live by. 


When somebody returns from a trip to Italy they will inevitably tell you about the perfect pasta they had in that old piazza, the beautiful architecture in Rome or the afternoon they spent drinking wine in the Tuscan hills. While all of these things make Italy an amazing place to visit, they can often overshadow the incredible natural beauty of this part of the world.

From the red-hued peaks of the Dolomites in the north to the precipitous crags of the Mediterranean coast in the south, there aren’t many other places in the world with such geological diversity. Having been lucky enough to visit Italy once before without my bike, I knew that if the opportunity ever presented itself again, I’d be crazy not to take my bike and ride to all of those mountains and coastal towns I’d glimpsed from the train window.

So earlier this year, when I found out we would be travelling to Italy for work, it was never really a question – the bikes would be coming along and we’d spend a couple of weeks, after our work commitments of course, exploring as much of Italy as possible. In 12-days. 


Unlike our last trip to Iceland, where we spent most days battling the elements just to reach that day’s destination, we would be taking an entirely different approach in Italy. Rather than constrain ourselves to tight deadlines and minimum distances we would base ourselves in a couple of locations and then see what we could find from there.

The rules were pretty simple. If there was a road or a trail that looked interesting, then we would be obliged to take it. Moreover, the success of the day’s ride would not to be measured by the total number of kilometres travelled or metres climbed, but by the number of times we stopped for food, wine or photos.

The feeling of setting off for the day without a fully-fledged plan of where exactly it is you’re going is one of the best things about riding bikes, and something I don’t do enough of these days.

A bridge over a cliff near the ocean in Italy.

While I love the physical challenge that this side of cycling provides, I also crave those days where you’re just riding around for the hell of it. Nowhere to be, simply riding through the countryside stopping whenever, and wherever you want. This was the plan for Italy, and what better place to do it.

So within a couple of weeks of hatching the plan, Dave, his girlfriend Maddy, and I were off to Italy with bikes, film gear and a very vague itinerary in tow. After watching our last couple of trips from afar, Maddy had decided that enough was enough – she wasn’t going to miss out another one of our spur-of-the-moment mid-year cycling adventures.

Three people sitting on a bench overlooking the Italian mountains.

Having watched a couple of the stages in the Dolomites in this year’s Giro d’Italia, I didn’t think there’d be too many surprises on our first day in the mountains. But I’m afraid to say that the TV images didn’t come close to capturing the magnitude and the beauty of the Dolomites.

Riding up the never-ending series of switchbacks of Gardena Pass, with the sun beginning to illuminate the towering limestone walls on either side of the road, there was a certain aura that couldn’t possibly be replicated in any photo or film. (And yet, that’s exactly what we’ve attempted to do with the photos you see here, and the video you can find below!)

From the green meadows and rocky pinnacles of the Dolomites, to the gently rolling hills of Tuscany to the jaw-dropping coastal roads of the Amalfi Coast, Italy presented us with some of the most incredible landscapes (and food) anywhere in the world.

A wooden pier in Italy.
A mountain in Italy with a small cabin on top.
Two cyclists riding down a winding mountain road in Italy.

While we’re never going to be able to perfectly recreate the experience of being there in person, hopefully the video below comes close.

For more from this trip, be sure to check out Jason, David and Maddy’s vlogs from Italy. NorthSouth is the collaboration between Jason Stirling and David Fletcher. Click through to the NorthSouth website to see more of their adventures or check out their Instagram page.