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Under the Tuscan Sun

23 January 2024

Words & Photos: Brett Cotter

As the curator of The Big Bike Film Night I’m always thrilled to hear how people are inspired by films in our collection, and then go off on their own adventure whatever that may be: building a bike, helping build a trail, or riding a trail that they’ve seen at a screening.

After watching 'L'Eroica' (The Heroic), in our 2023 collection, the colourful character Luciano Berutti and the alluring Tuscan landscape inspired and captivated me. The L'Eroica route was firmly locked in on my bike radar - but when could it happen?

Luciano Berutti on the L’Eroica route. Photo: Marco Rimondi.

I deliberately left a gap in the BBFN Australia schedule during September/early October for my own leisure. All sorted, I could say "Ciao Italy!", along with a trip afterwards to Scotland, to help with the screenings over there.

Creator Giancarlo Brocci, together with 92 'hunters of feelings and emotions' – as he called them – started the first edition of L'Eroica in 1997, combining challenging routes, magnificent landscapes, and unforgettable refreshments in a unique way. The official L'Eroica ride starts in Gaiole in Chianti and is held on the first Sunday of October, taking place over a 24-hour period, and (these days) draws thousands of avid cyclists from all over the world. It dishes up a mix of gravel and pavement over a variety of courses from 50 to 207 km distance. And... to make it even more challenging, you have to ride this on a vintage bike of 20 years of age or older.

Giancarlo Brocci and Luciano Berutti at the start line. Photo: Marco Rimondi.

Is this story about that? No, not this time. I know my limitations... so I crossed-off that massive one-day effort for another time. My passion and my pursuit were to experience the 207 km permanent route in a more relaxed way with the mesmerising countryside of the Val d'Orcia beckoning me to ride at my own pace, over a 3-day period on a gravel bike, before the 'official' L'Eroica ride event on Sunday 1st October 2023.

Leading up to my arrival in Italy, I read about and researched the circuit; it can be ridden year-round with Gaiole in Chianti, located north-east of Siena, being the preferred start. Without transport, it was challenging getting there and back, so I decided the best place to start was in the UNESCO World Heritage Site and medieval town of Siena. I could fly into Pisa, catch a train to Sienna and hire a bike there too.


Siena has an incredible history and its fan shaped central square was the perfect starting place. It holds the annual Palio di Siena; a horse race with ten horses and riders, bareback and dressed in stunning colours of their city wards.

Piazza del Campo and its red bricked buildings in Siena.

I’d contacted Anima Toscana, a bike-rental specialist there, and hired a Scott gravel bike for 4 days; the staff were happy to help and even provided a front bag/pouch to pack goodies into.

My weapon, the Scott gravel bike I was to ride L’Eroica on.

Ideally, I didn’t want to carry too much on the trip, so along with the front bag I had my Osprey Escapist 30L backpack with a change of light clothes, walking shoes, Lezyne front and back lights, tools, and other incidental travel stuff. The weather forecast looked amazing, I was there in late September, and it was still in the high 20’s – no need for the Ground Effect Storm Trooper jacket this time round.

I’d nutted out that with the route being 207 km, I could divide each day into a casual 70 to 80 km ride and in advance I had booked the first night's accommodation at the small comune of San Quirico d'Orcia, 75 km to the south, giving myself plenty of time to get there (well... so I thought).

"It's not an adventure unless something goes wrong", is a great old saying and I can laugh now at some of the going-ons that first day. While exploring Siena, I found a boutique grocery/deli shop with an incredible collection of Tuscan delicacies, including: cheeses; cornettos ('little horns' or croissants); olive oil; wines; and the local panforte, a treat with a chewy nut and fruit combination, something that I thought I deserved for the trip. However, as I realized later that morning, when you combine cobbles, gravel, lots of rattling handlebars and an open panforte wrapper, suddenly your front bag resembles a drug lord’s stash with fine white powder everywhere, except this white powder was 100% pure icing sugar; thankfully it was easy enough to clean. Only an hour further down the country road, a shoe cleat decided to work itself loose and I lost a screw, causing me to take a tumble when I couldn’t unclip. It was easy enough to change into my left foot walking shoe and have one foot clipped in, and one not clipped in, "no problem".

Appropriate footwear for riding 207 kilometres.

Onwards and upwards, I climbed a small hill and entered the charming hillside village of Murlo, where a cat sprung out from a side alley and took off in front of me. A real game of cat and mouse began as we weaved through the narrow alleys together, before the cat leapt off to the side and I continued on the route. The day's temperature was reaching its high of 28C and thankfully I found that the villages I was passing through had small water fountains to refill my water bottle.

Some of the picturesque water fountains along the route.

The day's route ascended one of the most challenging segments of the whole of the L'Eroica route, the Castiglion del Bosco. It was mind-blowingly beautiful with its ancient cypress tree lined boulevard approach, and I was on track to reach the small 16th century medieval hill town of Montalcino, which was 15 km away. This was the climb of the day, scattered with 12-15% gradients on three interconnected hills over a 470 metre ascent. The temperature was fiercely hot, but I was in my happy place.

The Castiglion del Bosco climb.

After 12 km I stopped to take a photo on my phone, and it was there, looking through the front pouch, that I realised somewhere during the last 6 km or so, my phone must have fallen out. I checked my backpack, and rechecked the pouch, and rechecked my backpack, and rechecked the pouch, yup... it was definitely not there. My head was spinning (not from the sun this time), fortunately I had my credit cards with me in my bike shorts, so paying for things wasn’t an issue; the main worry was more about finding out where I was staying tonight and other nights. I remembered that I’d passed a grand hotel 5 km earlier; I could backtrack and visit there, hopefully use a computer to find my accommodation bookings. So I started to retrace my ride back down the hill with a searchlight mentality, my head bobbing from side to side scanning across the road as I rode, in the infinite hope that somewhere along the way I would spot my phone. While descending, my brain was already thinking through a multitude of possible scenarios if I couldn’t find it, and after four long and slow kilometres down the winding gravel road, sitting in the loose shingle on a curve, there plain for all the world to see, was my phone, still intact, not run over by a marauding car. I don’t think I could have been happier; luck was on my side.

One very happy camper!

Resuming the climb back up the hill to Montalcino, with the intense heat of the afternoon sun, I was starting to feel the strain of the ride. Arriving at the hill town and after a quick snack it was time to admire the views from the Montalcino Castle that looked out over the vast sway of valleys and rolling countryside, old oak trees, picturesque vineyards and olive groves. It was a wonderful feeling of satisfaction and I felt really uplifted being there.

The views from Montalcino.

Leaving town, it was a thrilling descent weaving around corners on the paved road down to the valley floor to return to another country road, passing vineyards and wineries with captivating cellar doors. As I rode, I snaked over, around, and passed valleys and hills on this glorious white ribbon road, in the low angled sun, with stunning silhouettes of cypress trees to arrive at the charming comune of San Quirico d'Orcia at twilight, to find my accommodation. What a day.

Shadows on the rolling hils, and silhouettes of cypress trees leading to San Quirico d'Orcia.


After a hearty breakfast, it was time to resume the ride; I threw the backpack on and walked my bike along the cobbled alleyways of San Quirico d'Orcia towards the centre of the village. The quiet centre I rode into at 6:30pm last night had completely changed, now lined with bustling pop-up tents and caravans stacked with souvenirs, all ready for the tour buses and the tourists to arrive. Quickly leaving that behind, I found the markers for the L'Erocia route, and began today’s journey on the white roads.

As I was riding and taking the trail in, I was a bit confused, looking at the trail in front of me and the scenery; why weren't we riding in the valley? Instead, the country road steadily climbed a ridgeline overlooking valleys either side, and at that moment I realised – the views were the answer. The scenery was completely different from yesterday, more open pastures and fields used for agriculture, and farms open for agriturismo (farm stays). The country road led to a small hilltop village called Lucignano d'Asso, and as I rode through it, a group of motorbikes roared past me and turned off on a side road, not really interested in this lovely little village with its majestic views; for me, it was a treat to ride around the comune and appreciate it for its simplicity.

Abandoned homestead in the Val d'Orcia, and the tiny village of Lucignano d'Asso.

From the village, the descent on mixed stone road was vicious, it felt more appropriate to be on a mountain bike for this section and I was happy that I had the skills to navigate safely through the rocky terrain. By the time I reached Percenna and weaved my way through the back lanes to the town centre, I was ready for lunch.

Bikes, bikes, bikes at Percenna.

The village square had plenty of cyclists sitting outside relaxing over food and drinks, and there was a multitude of walkers present too. I chatted to an English man with his sturdy backpack who was undertaking the Via Francigena, the road to Rome pilgrimage route. I marvelled at his and other walkers’ stamina to do such a long-distance journey by foot.

On leaving town, the area I entered was very isolated and it was a strain getting up the constant hills with the sun glaring down.

A shot of the unpaved gravel road on leaving Pecenna.

In the distance, I spied two riders and aimed to catch them. They were retired Italian gentlemen, one on an e-bike, the other a touring bike. It was nice to have a quick chat with them in broken English/Italian. Upon leaving they enthusiastically yelled "go, go, go".

This area I was riding through was easily the most challenging on the trip with steep descents and gullies to climb back out of. Finally I rolled into the quaint comune of Castelnuovo Berardenga and found my accommodation - an agritourism facility with a winery that had the strong, heady aromas of grapes being harvested and red wine fermenting.

After changing, I googled ‘restaurants locally’ and found Bengodi Enoteca Ristorante, a place that was within easy walking distance. One of the restaurant's specialties was risotto. Greeted by the host, I was shown to a table and naturally ordered the risotto. Soon a staff member brought an empty plate to my table, then another staff member carried the steaming risotto in a massive 15-inch pecorino cheese round to the table, then proceeded to dexterously use two spoons to shave off the cheese and at the same time mix the cheese shavings into the risotto, before finally spooning it onto my plate. It was delicious. After that dinner experience I strolled back to my accommodation, stoked on life and ready for tomorrow – the final day of riding.

Bengodi Enoteca Ristorante in Castelnuovo Berardenga.


At the local supermarket I bought breakfast – I was getting a taste for cornettos and had one with nutella and another dripping with lemon curd, they were scrummy. Returning to the quaint square where Bengodi Enoteca Ristorante was, I sat under a wisteria wrapped pergola and enjoyed breakfast, waving to the restaurant host as he opened up. As I ate, a group of older Italian ladies strolled by, making a fuss over each other, then a Piaggio Ape (a small 3-wheel classic Italian van) slowly entered the one way street. One of the ladies sauntered over to the van-driver and presented him a rolled invitation tied with a brilliant red bow. They chattered and laughed, oblivious that by now, a car had pulled up behind the van waiting patiently to go forward. Such a site to behold, very Italian.

A Piaggio Ape and my bike hanging out together.

The day was even hotter than the previous, and it was a major effort climbing hills. But it was the final day, and I was in Chianti 'wine' countryside, life couldn’t be better.

I rode past gnarly old olive trees, vineyards and wineries with compelling signs welcoming you to 'Azienda Agricola Vallepicciola' and 'Tolaini Winery'. They looked inviting and spectacular. Then I passed the Chianti Sculpture Park with its sophisticated entrance arrow made of marble. So chic, so stylish.

A roadside statue close to the Chianti Sculpture Park and the entrance sign to the Sculpture Park.

The village of Radda in Chianti was my next stop. It was bustling with tourists walking the streets, sitting in outdoor cafés and taking it all in. On from here it was one of the most breathtaking descents I enjoyed on the route, riding along a ridgeline past Castello di San Donato in Perano, a sixteenth-century fortified farm perched on a hilltop with an outstanding view.

The ridgeline I was riding along, by the Castello di San Donato in Perano.

My destination was close. Winding my way down, there it finally was - the comune of Gaiole in Chianti where L'Eroica was born in 1997, and where the 2023 edition would begin from in three days’ time.

There was plenty of activity going on – temporary buildings being erected, bikes on display and cycling enthusiasts everywhere along the main street – in cafes, bars, and shops.

Stalls in Gaiole in Chianti getting set up, ready for the BIG day.

Riding through the town I found a bronze statue of Luciano Berutti with his favourite bicycle, a 1907 Peugeot. As I pass a café I heard a voice yell, "go, go, go", and looked to my side I saw the two Italian gentlemen from yesterday waving to me, enjoying lunch with a beer. They were finishing their ride here and it was great to see them again.

Window signs in Gaiole in Chianti celebrating the event, and the bronze statue of of Luciano Berutti with his 1907 Peugeot.

There was one thing I wanted to do here in town, which was a compulsory stop into the official L'Eroica store to buy a t-shirt. Then it was time to ride the final 31 km back to Siena.

The next leg was amazing, on a paved road from La Madonna Village I veered up a cypress lined chalk boulevard dedicated to Luciano and named 'La Strada Luciano'. It switchbacked up the hill and I emerged to another panoramic view, and over to my right the stunning Castello di Brolio, with slope laden rows of vines stretching forth for the eyes to behold.

The entrance to 'La Strada Luciano' and the view looking back to Castello di Brolio surrounded by vines.

I decided to pick some grapes and revel in the view. From there, the 9 km descent from the castle on gravel was mind-blowing. I found myself inexplicably singing (in 'attempted Italian') a song Luciano had sung in the movie and laughing at what this trip had done for me.

At the small town of Pianella, I passed four cyclists enjoying a beer at a bar and happily waved to them, smiling and thinking that will be me soon, in Siena. It's mostly downhill from then on, but occasionally a hill rose in front of me and reminded me how hilly it was.

On the outskirts of Siena, I inadvertently turned up the steepest street to the centre and found the final leg begrudgingly beyond me; having to push the bike up the road until the gradient was easier to ride. Finally arriving at the Piazza del Campo for the obligatory photo was a moment I will treasure forever.

That’s my Tuscan story, inspired by The Big Bike Film Night and Luciano Berutti.

Me besides a road marker of the L'Eroica route, and back in Siena at the Piazza del Campo (wearing the same salty, crusty riding shirt).

I came away from this ride brimming with enthusiasm for the route and the Tuscan landscape, and hopeful to return and explore more of this area.