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5 Days of Soulful Riding with Matteo Cigala

Some trips challenge your legs. Others stir your spirit. And then there’s Tuscany Gravel, a week-long journey that does both, brilliantly.
Led by former pro cyclist and gravel enthusiast Matteo Cigala and supported by Marine Lenehan this ride was not just a tour; it was a rolling immersion through one of Italy’s most iconic landscapes. Over five riding days, we climbed ridgelines, coasted through medieval towns, indulged in Tuscan cuisine, and shared in a collective sense of wonder, and yes, just enough suffering to feel we had earned the magic.

Day 1: Arriving in Donoratico – The Calm Before the Climb

We landed in Florence and Pisa before converging on Podere Conte Gherardo, a tranquil country estate nestled near the Etruscan coast, late in the evening. Warm evening light filtered through cypress trees as we settled in, met the crew, tuned our bikes, and shared our collective cycling experience. Matteo’s easy confidence and deep local knowledge were immediately clear, we knew we were in good hands. There was some nervous energy amongst those of us who had yet to experience gravel.

Day 2: Donoratico → Fabbrica di Peccioli

Distance: 98 km | Elevation: 1200 m
The first real pedal strokes brought us through a sun-dappled mosaic of vineyards, oak forests, and rolling gravel lanes. The route was fast and flowy, with just enough punchy climbs to wake up the legs. Espresso stops were not as frequent as my poorly toned legs felt necessary, but it was essential to press on through the gorgeous view of hilltop villas and distant sea. The baking Italian sunshine working on our pale and pasty Irish skin. The mostly flat morning had the “roadies” amongst us wondering what all the fuss was about. This was handy. Beautiful, but no harder than road cycling.

The afternoon that put me firmly back in my box. I had concluded that even a 1% descent feels like a hill on gravel, and there is an unrelenting rolling nature to it, lots of micro-accelerations, and a lot of demand for particularly good bike handling. We arrived in early evening to Agriturismo Diacceroni, perched on a quiet ridge with panoramic countryside views. Think farmhouse charm, open-air dining, and food so fresh it may have been picked that afternoon. The staff sent us homemade pizza until we were fit to burst, watching the intensity of the sunset deepen. With weary legs, we made our way to bed to the sounds of cicadas and clinking glasses from nearby tables.

Day 3: Fabbrica di Peccioli → Colle Val d’Elsa

Distance: 70 km | Elevation: 1500 m
Do not let the shorter distance fool you, this was a big day. The gravel got steeper and rougher, and the views more dramatic. We traversed a series of ridge roads with sweeping views of classic Tuscan valleys, flanked by vineyards and castles that seemed unchanged since the Renaissance. The uninitiated to gravel got a sharp dose of reality today, and we made our way through very rough chunky rocks both ascending and descending. Our experienced American friend christening them “gnarly.”

The descent into Colle Val d’Elsa, a fortified town with cobbled streets and hidden piazzas, was pure joy. We landed at Relais Della Rovere, a 12th-century abbey turned luxury hotel, where we lounged by the pool and dined like royalty in vaulted stone halls. This hotel was truly a taste of Italian luxury, reminding me that Matteo and Marine really know how to pick them. One of the other guests, an Italian maestro on the gravel bike revealed himself to be similarly talented with the wine list, and he became our tour sommelier for the remainder of the week.

Day 4: Colle Val d’Elsa → Pienza

Distance: 108 km | Elevation: 1700 m
This was the Queen Stage, the crown jewel, and the most demanding ride. The Crete Senesi region greeted us with its iconic clay hills, dramatic ridgelines, and ancient roads that had our tyres dancing on loose gravel. Every climb brought us deeper into the Tuscan soul. The climbs in the first half of the day were intense, even with the gearing on gravel bikes. The first climb out of Colle Val d’Elsa was a cobbled masterpiece that was 1.3km long averaging 15% and reaching 30% in spots (the most exciting moment is finding when you get to the top that there is an elevator). But we faced other long, steep, and rough ascents. Adapting quickly to the differences in road bikes and gravel bikes, with quickly churning legs in an uncomfortably high cadence, sat in the saddle to keep the grip on the back wheel. Lunch was in Siena, the glorious Italian home of the “white roads” of Strade Bianchi fame.

By the time we reached Pienza, in the evening time, a UNESCO-listed town famed for pecorino cheese and renaissance architecture, we were exhausted and elated. We had an aperitif overlooking the beauty of the Tuscany hills, surrounded by wedding photography shoots and Instagram influencers waiting to catch the perfect moment. Dinner at La Terrazza Del Chiostro was an emotional one: warm lights, sunset views over the valley, and plates that tasted like poetry.

Day 5: Pienza → Marina di Grosseto

Distance: 126 km | Elevation: 1650 m
This stage felt like a transition, from mountains to sea, from introspection to celebration. We weaved through olive groves and cork forests and finally descended to the Tyrrhenian coast. The salty air felt like a reward. This day was long and extremely hot, but we were gaining confidence on the gravel now, and the watts were starting to come. Too much power for one of the guests, who has almost zero experience on the bike. Such a warrior, never knowing when he was beaten, pushing everyday to be near or off the front. Too much power on a loose gravel descent saw him take a small spill, but again, heroic to the last, dusted himself off and pushed to bridge across to the lads at the front again.

We rolled into Hotel Terme Marine Leopoldo II, our seaside sanctuary, where we dipped tired legs in the pool and swapped ride stories over seafood at Ristorante da Nevo. The mood? Euphoric.

Day 6: Marina di Grosseto → Donoratico

Distance: 104 km | Elevation: 1000 m
The final stretch was smoother and more relaxed, like a proper farewell ride. Laughter replaced grimacing. Legs, though weary, seemed lighter, maybe from the mileage or maybe from the bittersweet awareness that this was the end. There was a fabulous moment in the forest where we had an absolutely incredible stretch of single track that must have gone on for 45 minutes to an hour. Relentless, beautiful, up, and down, whipping left and right, through mud, streams, branches, it was easily the most fun I had ever had on a bike. The route took us through quiet coastal towns and pine forests before circling back to Podere Conte Gherardo, where it all began. Beautiful clifftop paths that gave tantalising glimpses of the cool and refreshing sea, we stopped briefly to chat with some wizened Italian cyclists who looked stronger and fresher than me, even in their mid-eighties.

We wrapped it all up at Locanda Menabuoi, one last Tuscan feast, one more round of Chianti, and a few emotional toasts to new friendships and shared adventure.

Reflections from the Saddle

Tuscany Gravel wasn’t just about riding bikes. It was about slowing down, even as we sped up. About connecting, to the land, to the culture, and to each other. Matteo Cigala brings a rare mix of pro-level expertise and heartfelt hospitality. You will never feel rushed, but you will never feel unchallenged.
This trip gave me sore legs, stunning memories, and a stronger love for gravel riding. And it reminded me that sometimes the best way to discover a place, and yourself, is by bike.

Would I do it again? Absolutely.
Would I recommend it? Without hesitation.
Would I trade a week on the bike for anything else? Not in a million switchbacks.