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.

  • Andy B

    wow. stunning.

  • Ajh

    Hating my office existence when you see things like this…….

  • donncha

    Thanks! I’m planning my Italia trip for next year to coincide with some of the Giro, and had been making notes during this year’s Giro. Corvara was earmarked for a visit, so great to see more information and stunning photos!

    • Spencer Martin

      I just returned from a trip to Corvara. I cannot recommend it enough. Great food, Incredible roads and awe-inspiring views.

  • Simon Gamble

    Is it possible to get a map showing where they rode or strava routes?

  • Steve

    Looks incredible, off to the Dolomites in October. Don’t understand though, why are they riding with rucksacks?!

    • Aigars Paegle

      About rucksacks – the weather in the Alps may change dramatically in few hours time and it’s normal that at the top of climbs it’s much more cooler. For example, It may be even close to 0C at the top of Stelvio in July. A SAG van is very useful there.

    • Enjoy your trip you’ll love it! The Dolomites are incredible.
      Re rucksacks… We’ve been riding with backpacks for years now and are used to it :) Lugging film and photography gear around isn’t easy (especially if you have a drone!) and you can’t strap a drone to a set of panniers. In order to get certain shots we have to run up hills or climb through bushes etc etc. We just personally feel it’s easier to work with backpacks for this reason.

  • Il_falcone

    Wow! Just wow! Thank you for sharing.

  • Allez Rouleur

    First of all, these stories are KILLERS when you’re sitting at work at a desk:(

    Secondly, I can’t imagine biking any sort of distance with a backpack. Anything over 30-45 minutes and my neck and shoulders start to get sore. Why not go for panniers? The Axiom racks work even on road bikes.

    • Hey Allez. Panniers are a good option for touring but they don’t work too well with our type of adventures for a number of reasons. Please see my comment above to Steve who asked a similar question.

  • winkybiker

    Nice shots. It might have taken a while to get the shot of Positano without a car in it, though. The Amalfi Coast drive is car-fucked from one end to the other. And don’t even talk about Naples/Sorrento.

    • James_Casper

      Don’t need a car to do either.

      I’m currently in Arienzo, a couple of kms the Praiano side of Positano.

      I’ve take a few shots along the coast with no other vehicles in sight. The trick is to take the shots before 10 am – the roads are pretty quiet, or after about 7.30, once the day trippers have left.

      No issues with my bike. Heaps of cyclists riding the coastal rode.

      You’re right thoug; Not sure why anyone bothers with their cars. It takes 2 to 2.5 hours from Salerno to Positano on bus / or by car.

      Ferry is so much cheaper and quicker (and bike friendly).

      Same with Naples and Sorrento. You can take your bike on the circumvesuviana train if you don’t feel comfortable with the road. The ride between Sorrento and Positano was surprisingly quiet. Beautiful scenery too as you come down into Positano.

      Also been here from the second week of September, and with school holidays over, it’s like a different world. Even driving the Amalfi coast is ‘doable’.

      Would def suggest come in mid Sept.

      • Wily_Quixote

        i was there over christmas. a different world.

        • James_Casper

          Be an amazing (and cheaper) place to visit in Winter.

          Loving it know – nice to get have some ‘insider knowledge’ on how / what to see and avoid he crowds etc.

  • Jeremy

    Stunning video. Can anyone comment on the lack of traffic?

    • James_Casper

      See my comment above.

    • The early bird catches the worm :) Get up early and the traffic is non existent.

  • Bella Molloy

    Fantastic video to get me all excited for the next adventure. Fortunate enough to have come back from a 4.5week cycling holiday through France and Italy. We didn’t get to the Dolomites but rode in the Alps and along Lake Como. Only downer for us were the crazy Italian drivers. We pulled the pin on riding a few days earlier than planned after a few too many near death experiences with cars whilst cycling around the Lake Como area. Despite lots of cyclists around the drivers are nuts. I found though, riding in the hillier areas and also in the Alps on the alpine passes (Gavia and Stelvio) far more bike friendly. France does take bike friendliness to the next level though.

    • Zucco415

      Riding a bike around the lakes and especially Lago di Como during peak summer months is a No, No! Early Spring or Fall is a much better experience but there are so many more appealing places to experience in Italy

      • markpa

        Was lucky. Our stay coincided with Giro Lombardia, early October. was great to ride up to Madonna del Ghisallo with 100s of others. Also a good time tourist number wise.

    • Tricky Dicky

      Yes, unfortunately the Italian Lakes make for really difficult riding – one side of Lake Garda is a series of tunnels with coaches and Ferraris playing chicken at 100km/h. There are some great bike paths north of Garda that can take you all the way through Trento and onto Bolzano though.

      To the poster above planning on going to the Dolomites in October, I was there 2nd/3rd week of September and it was turning pretty cold with snow risk at times. When descending at speed I thought I was going to die of hypothermia!

      IMO, a massively under-rated area to ride in Italy is the Appennines (base yourself in Le Marche somewhere). Loads of great riding – and local racing / gran fondos – without the traffic. Unfortunately, the recent earthquake might make it unpopular for a while.

  • Wily_Quixote


  • Zucco415

    Fantastic video and thanks for sharing. Yes, we only die once….so live life to the max.

  • Nice piece! Now you know why we began CycleItalia almost two decades ago. NOWHERE else offers the cyclist and cycling enthusiast what the Bel Paese does. Of course we’re going to suggest you enjoy it with us, but no matter how you do it, DO IT! Buying a new bicycle won’t change your life much, but spending that same money on cycling in Italy WILL!

  • David9482

    Unbelievable stuff boys and girls. Thanks so much for putting this together.

  • exemplary1

    Bravo, keep these articles coming.

  • Mark Studnicki

    We have lived in Italy for quite a few years and see much of this on a regular, everyday basis. very blessed to be able to ride this daily and live my dream.

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