Roadtripping Italy

Exploring Tuscany, the Amalfi Coast and the Dolomites by bike

Words: Jason Stirling | Photos and videos: David Fletcher, Jason Stirling & Maddy Dick

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.

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 kilometre 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.

With the advent of bike computers, Strava and Zwift, cycling has become more and more appealing to our competitive nature – a numbers game that rewards structure and penalises spontaneity. It’s easy to forget why we got into it in the first place.

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.

If we thought we were in for a typically relaxing holiday in the Mediterranean though, our hopes we quickly dashed upon our arrival into Italy. Before we had even made it out of the airport car park, we found ourselves driving the wrong way down a one-way street, getting angrily gestured at by a local driver, accidentally hitting the emergency phone button before finally reversing the hire car into a pole on the side of the road (see video to the right). Welcome to Italy!

I had completely forgotten that while Italians are renowned for their fun-loving and leisurely lifestyle, these traits tend to disappear as soon as they get behind the wheel of a car! In retrospect, it was actually a two-way street but the fact we thought it wasn’t probably says a lot about driving in Italy.

After finally navigating our way through the chaotic roads of Northern Italy and getting a couple of meetings out of the way, we eventually arrived in Corvara in Badia, our temporary home in the heart of the Dolomites and a far cry from the frenetic streets of Milan. This is what we came to Italy for.

Despite the ominous weather forecast, we were greeted by near perfect conditions for our first day of riding so we quickly assembled the bikes and hit the road just before dawn – the perfect way to start our 12-day journey through Italy.

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.

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

Finally, a special shout out to photographer-riders Ashley and Jered Gruber for sending us on the hardest 38 kilometre ride known to man. Even if we hadn’t got lost, I think it still would’ve been the most difficult day of the trip!

For those who are interested in going off the beaten path (quite literally) and seeing some of the most beautiful parts of the Alta Badia Valley, you can follow the Grubers’ exploratory route here. If I only had one day to ride in Italy, then this is where I’d be going.


CyclingTips would like to thank Specialized for making this adventure possible. 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.