A Ride Through Cycling History: A Bike Tour on the Iconic Gravel Routes of Tuscany

Ruth Bergman
Apr 21
14 min read

Updated: Apr 30

Following the Tracks of Legends: Tuscany Calls to Gravel Cyclists

Italy has long been a place where cycling is more than a sport—it’s a way of life. From the alpine passes of the Giro d’Italia to the cobbled streets of ancient towns, the country reveres its two-wheeled heroes and the roads that made them. And nowhere is this cycling heritage more alive than in Tuscany.

Rolling hills, cypress-lined lanes, medieval hill towns, and sun-drenched vineyards make Tuscany a feast for the senses. But for cyclists, it offers something more: the iconic strade bianche—the white gravel roads that snake through the countryside like dusty threads stitching together centuries of rural life and racing history.

These roads are at the heart of two of the most storied gravel events in the world. The Strade Bianche, a modern professional race, challenges elite riders with steep climbs and loose gravel that turn every kilometer into a test of skill and resilience. Meanwhile, L’Eroica celebrates the romance of vintage cycling, inviting riders to don wool jerseys, ride steel-frame bikes, and honor the grit and glory of bygone eras as they retrace classic routes.

These events have helped transform Tuscany into a mecca for gravel cyclists. But you don’t need a race number to experience the magic. Inspired by these great traditions, we planned our own journey on two wheels—part pilgrimage, part adventure—through the timeless landscape of Tuscany. What follows is the story of that ride.

The Gravel Experience: Following the Routes of L'Eroica & Strade Biance

We arranged our tour with Cicloposse, the same expert outfit that had guided us through the rigors of the Challenge Tuscany ride years ago. This time, they took the reins on planning a gravel adventure—organizing charming hotels along our route, equipping us with sturdy gravel bikes, and providing detailed GPS maps that stitched together a journey through the heart of Tuscany’s white roads. Their experience showed in every detail, from the pacing of the itinerary to the mix of terrain.

Our route combined segments from both L’Eroica and Strade Bianche, giving us a taste of the historic and the heroic. Riding these roads is a very different experience than road cycling. On gravel, you can’t zone out. You’re always reading the surface, adjusting your line, shifting your weight—there’s no autopilot here. It’s immersive, demanding, and deeply rewarding.

We quickly learned that not all gravel is created equal. Some stretches, especially those associated with the Strade Bianche, featured super-fine, compacted gravel—what is referred to as champagne gravel. These were an absolute joy to ride: smooth, grippy, and fast, with just enough crunch under the tires to remind you you were off the tarmac.

Other sections were more... rugged. One day, we followed a path that turned into what felt like an old riverbed, studded with large, uneven river rocks. Our guide from Cicloposse had warned us, “It’s rocky, but beautiful.” She was exactly right. It was bumpy, technical, and hard on the wrists—but it also led us through some of the most stunning, remote countryside we saw on the whole trip.

Climbing on gravel is its own kind of challenge. The inclines are often steeper than what you'd find on the road, and traction is never guaranteed. A single loose stone under your tire can end a climb with a foot-down, and momentum is a fragile thing. Downhills, meanwhile, are less about coasting and more about managing the jolt—jarring at times, with your hands clenched on the brakes and your body braced for ruts and washouts.

But here’s the trade-off: when you’re on the gravel, you have Tuscany to yourself. Cars are rare. Even other cyclists are few. The strade bianche wind through vineyards, olive groves, and oak forests, past stone farmhouses and forgotten chapels, with nothing but birdsong and the crunch of gravel beneath your wheels. It's not the easiest way to see the countryside—but it's undoubtedly the most intimate.

And then, from the quiet of the gravel, you round a bend—and suddenly, you're face to face with Tuscany’s iconic magic. Each day brought us not just kilometers of riding, but moments that grounded us in place: a chapel catching late afternoon light, a fortress clinging to a hilltop, a piazza alive with local chatter. These weren’t detours from the ride—they were the ride. What follows are the places that stayed with us, the snapshots of Tuscany that stitched themselves into our journey. Some are well known, others hidden in plain sight, but each offered a moment where adventure met beauty, and time slowed just enough to take it all in.

The Convent: Il Chiostro

In the heart of Pienza, tucked beside the town’s main church, we found one of the most memorable stays of our tour: Il Chiostro, a former convent turned hotel that seemed to hold centuries of quiet stories in its stone walls. It took a moment to find the entrance, tucked away behind the church, but stepping inside felt like entering a different time.

A peaceful cloistered courtyard greeted us, ringed by elegant stone arches and shaded by old trees. The noise of the town faded behind thick walls, and a hush seemed to settle over everything, as if the convent still carried the echoes of monastic life.

To reach our room, we climbed a narrow staircase carved of stone so old it had been worn to a soft concavity—the footsteps of countless nuns gently etched into each step. The place was full of such quiet detail: wooden shutters, high ceilings, the cool breath of ancient masonry.

But the real showstopper was the balcony. Perched above the Val d’Orcia, it offered a sweeping view of Tuscany’s rolling hills—golden fields, patchwork vineyards, winding farm roads. After a long day’s ride, we sat there with cold drinks in hand, watching the sun sink behind the distant ridgelines, painting the landscape in warm amber and soft lavender. It was one of those rare moments that feels both well-earned and entirely unhurried.

Il Chiostro wasn’t just a place to stay—it was an experience in itself, a perfect blend of history, location, and tranquility that made it hard to leave. But as with all great bike tours, the road ahead was calling.

The Sanctuary: Tempio di San Biagio

Each day of our Tuscan ride brought a perfect blend of cycling challenge and cultural reward. The gravel roads gave us solitude and scenery, but they also led us—sometimes unexpectedly—into moments of historical wonder. On our first day, we had just begun to settle into the quiet rhythm of the strade bianche, enjoying the peace and crunch of the gravel, when our route suddenly changed character.

The gravel ended, and we rolled onto a paved road—a welcome change for a moment—until we looked up and saw the steep climb ahead. The road to Montepulciano winds upward with purpose, and we shifted into low gears and settled into the grind. Around a bend, as we crested a rise, we were greeted by a magnificent sight: the Tempio di San Biagio, or the Sanctuary of the Madonna di San Biagio, standing gracefully at the base of the Montepulciano hill.

Built in warm travertine stone, the church is a masterpiece of Renaissance symmetry. Its bold, central dome and clean lines give it an almost otherworldly presence. Inside, soft light streams through tall windows, illuminating the elegant interior with a quiet, reverent glow. The sanctuary feels balanced and serene—architectural perfection grounded in the Tuscan earth.

But what made our arrival at San Biagio truly special was its setting. From the steps of the church, we looked back over the valley we had just climbed. Vineyards and olive trees stretched to the horizon, and our path curled below like a ribbon. The juxtaposition of effort and reward, of dust and divinity, was everything this ride promised.

The Well: Il Pozzo dei Grifi e dei Leoni

From the tranquil beauty of Tempio di San Biagio, our ride continued upward, this time along a steep, narrow stretch of paved road that led to the ancient gate of Montepulciano. I was quietly proud to reach the top—legs still spinning—as we arrived at the imposing gate. That sense of victory lasted right up until I looked back and saw Oren climbing the final, brutally steep section through the gate with what looked like casual ease. It was a friendly reminder that Tuscany always saves one more incline just when you think you’re done.

Inside the walls, we pedaled through narrow stone streets until we emerged into the heart of Montepulciano: the Piazza Grande. Surrounded by a mix of medieval and Renaissance architecture, the square feels like a stage set—each building distinctive, from the raw stone of the Palazzo Comunale to the refined facade of the Duomo. The square is both grand and intimate, worn smooth by centuries of footsteps and stories.

What captured my attention most, though, was the well—the Pozzo dei Grifi e dei Leoni, standing proudly at the center of the piazza. Topped by travertine columns and statues of griffins and lions, it’s part sculpture, part functional structure. It’s also a quiet symbol of Tuscan life: wells are everywhere in this region, from the grandest towns to the smallest farmyards, each one a testament to the communities that once depended on them.

This one, however, felt alive with activity. The Piazza Grande may be surrounded by historic buildings, but it’s far from frozen in time. It remains a hub for both locals and visitors, with families lingering in the shade, children darting playfully around the well, and townspeople crossing the square on daily errands. In the midst of it all, the well stands steady—a gathering point that, for centuries, has connected people to place.

The Chappel: Capela di la Madonna di Vitaleta

Late in the day, still some kilometers from Pienza, we found ourselves riding along one of the most delightful stretches of champagne gravel—that fine, smooth kind that feels like silk beneath your tires. The sun hung low, casting golden light across rolling hills stitched with vineyards and cypress trees. It was the kind of road that makes you forget the climb before and the distance ahead.

Then, unexpectedly, we came across something unusual for the gravel routes of Tuscany: parked cars. Lots of them. After a full day on quiet, near-empty roads, the sight of so many visitors felt strange. Curious, but too tired to stray from our route, we continued on toward Pienza, chalking it up to a missed opportunity.

Thankfully, Tuscany is generous with second chances. The next day’s ride—another loop from Pienza—brought us back in range of that same area. By then, I had learned what we had passed: the Cappella della Madonna di Vitaleta, a charming and secluded little chapel tucked into the countryside like a secret.

This time, I made the detour.

The road to Vitaleta is as enchanting as its destination—a winding gravel path lined with cypresses and soft fields, gently curving over low hills. As we approached, the small white marble façade of the chapel came into view, standing in crisp contrast to the earthy tones of the surrounding land. The setting is magical, with open vistas on all sides, and a quiet stillness that draws you in.

Though simple in design, Vitaleta’s beauty lies in its solitude and symmetry—a postcard come to life, perched perfectly in the Tuscan landscape. I was glad we turned back.

The Fortress: Rocca Aldobrandesca

When you're biking 50 kilometers a day, there’s plenty of time to see Tuscany—but only if you’re selective. The temptation to stop at every village, winery, castle, and café is very real, but the reality of daylight (and our lack of lights) meant we had to make careful choices. It’s easy to lose track of time when every turn brings something beautiful, and we had more than one evening where we cut it close to sunset. But one stop we didn’t regret in the slightest was Rocca Aldobrandesca, perched above the village of Castiglione d’Orcia.

At first glance, the fortress appears derelict—an old stone ruin, weathered by time and centuries of conflict. But stepping inside, the story of the Aldobrandeschi family begins to unfold. One of Tuscany’s oldest noble families, their influence stretched across the region in the Middle Ages, and this castle was one of their strongholds. What’s most fascinating is how the layers of history remain visible in the ruins. You can clearly trace the evolution of construction methods: rough local stone in the earliest walls, then brick and mortar as techniques and resources changed, and reused materials scattered throughout.

In one particularly striking corner, we even found granite projectiles—massive, round stones that were once hurled from trebuchets and catapults in siege warfare. They lay quietly now, like sleeping relics of a more violent past, a reminder that these picturesque ruins were once battlegrounds.

As with so many Tuscan landmarks, the setting of Rocca Aldobrandesca is part of its power. From the top of the hill, the view spills out over Castiglione d’Orcia, the surrounding patchwork of fields and ridges, and across to the Rocca di Tentennano, another medieval fortress commanding its own peak. It was one of those rare places where we could truly feel the weight of history—layered, lived-in, and left behind.

Espresso: Buonconvento's Cycling Culture

By day three of our tour, the rhythm of gravel riding had settled in—dusty climbs, quiet descents, and long stretches of peaceful roads rolling through the countryside. As we pedaled along a particularly scenic valley stretch, Strade Bianche signs appeared more frequently. And then, suddenly, we weren’t alone anymore.

We had arrived in Buonconvento, a town that sits at the crossroads of Tuscan charm and cycling tradition. For the first time on the tour, we were surrounded by other cyclists—some solo, some in colorful pelotons, all clearly drawn here by the same love for riding on the roads of Tuscany. The valley approaching town was dotted with riders, and once inside Buonconvento’s walls, we saw even more—chatting around café tables, refueling at bakeries, tweaking gears on sidewalks.

It was impossible to resist the vibe. We pulled into a bustling espresso bar, leaned our bikes beside a growing collection of carbon and steel, and joined the ritual. With tiny cups of strong coffee in hand, we soaked in the scene: a town alive with the spirit of cycling, where it felt like every corner had a rider or a story.

As we sipped, we stood before a permanent map of L'Eroica, proudly displayed along the main street of the old town. We traced the legendary route, recognizing familiar segments from our own ride, and planned for the climb ahead to Montalcino.

In Buonconvento, gravel biking isn’t just a trend—it’s a way of life, one that made us feel instantly at home.

The city gate: Montalcino

The climb to Montalcino was a long, steady grind—on pavement this time, not gravel—and we felt every meter as we wound our way up through the golden hills. Finally, the silhouette of the city wall came into view, a quiet promise that we were almost there. We circled the outer wall for a while, soaking in the dramatic views, before entering the city near the fortress, where we rode through narrow cobbled streets and sun-drenched piazzas.

We stopped at Petto’s Pizza on Piazza Giuseppe Garibaldi, a casual spot perfect for people-watching. As we rested with slices in hand, the town slowly spun around us—locals going about their day, the occasional cyclist dismounting with a clink of pedals, and the warm hum of life continuing as it always has in this hilltop town.

After checking in at our hotel, we explored on foot. A wine shop lured us in with the promise of tasting Brunello di Montalcino, and afterward, we followed our sweet tooth to a gelato shop with the wonderfully existential name: Gelateria Artigianale e Yogurteria “WHY NOT?”—a question we couldn't answer any way but yes.

Our hotel, Hotel Vecchia Oliviera, added one final, perfect note. It sits within the old city gate, and although the rooms are simple, the historic setting is unforgettable. Passing under that imposing stone arch, now repurposed as the hotel’s entrance, felt like stepping into a different century. We took our coffees out to the balcony, where the valley unfolded before us—a vast, peaceful panorama that made every climb, every dusty turn, and every bump in the road entirely worth it.

The City: Siena

This wasn’t my first time in Siena. I’d visited this iconic Tuscan city before—by train, in a much more conventional way. But arriving by bike, after days of riding gravel roads and winding climbs, felt like entering an alternate reality. The approach, like all towns in Tuscany, came with a long uphill road, but this one ended triumphantly at the massive, ornate San Marco Gate. We had to stop and document the moment. We’d made it.

Our route into the city took us on a cycling tour of Siena’s most famous piazzas. At one point, we took a quiet turn down a narrow alley and were suddenly spit out into Piazza del Campo—the dramatic fan-shaped square at the heart of the city. It’s the traditional finish line of the Strade Bianche, and for a moment we felt like we were part of that race’s storied legacy.

The ride continued, and with it, the crowds grew. Soon we found ourselves at the Piazza del Duomo, gazing up at Siena’s black-and-white striped cathedral, a piece of gothic art that feels more like sculpture than architecture. On the way to dinner, we passed Via Santa Caterina, home to the steepest climb in Strade Bianche—a punishing 16% gradient that we wisely chose to tackle on foot rather than pedals.

We closed out our city ride with a sunset detour to the Fortezza Medicea, where we looked out over Siena bathed in gold, the skyline etched with towers and domes. As exhilarating as it was to roll through Siena’s storied streets and follow the path of legends, we also found ourselves craving the quiet again—the whisper of gravel beneath our wheels, the solitude of cypress-lined roads and fields, and the peace of riding back into the Tuscan countryside.

The Castel Resort: Catello di Spaltenna

No gravel tour of Tuscany would be complete without a stop in Gaiole in Chianti, the proud home of L’Eroica—the legendary vintage cycling race that helped revive gravel riding as a celebrated tradition. Walking the cobbled main street, it’s clear that Gaiole lives and breathes L’Eroica. From shop windows lined with retro jerseys to road signs and framed photos, the spirit of the race is everywhere. Like many others before us, we couldn’t resist picking up our own L’Eroica cycling kits, a perfect keepsake to remember this special trip.

From Gaiole, it was only fitting that we rested our legs in true Tuscan style—at Castello di Spaltenna Exclusive Resort & Spa, a medieval castle turned elegant retreat. I’ve always loved staying in castles, and this one didn’t disappoint. Though it was too cold to take a dip in the pool, we still admired its panoramic views over the vineyards and hills, and we soaked in the jacuzzi, letting the warmth ease the accumulated miles from our legs. The castle’s restaurant served outstanding local cuisine, perfectly paired with wines produced from its own vineyard.

More than anything, staying at Castello di Spaltenna felt like living inside a Tuscan dream. We pedaled through a stone castle gate to reach our hotel, watched the sun touch the tower of the castle’s small church, and sipped espresso (or wine, depending on the hour) in quiet courtyards surrounded by ivy and roses. All around, the landscape reminded us: this is why we came—for the history, the beauty, and the blend of effort and indulgence that defines Tuscany.

From Gravel to Grounded: When Life Meets Adventure

I haven’t mentioned the dates of our trip until now, but it was October 7, 2023, when we woke up in Siena, ready for another day of riding. I sat quietly at breakfast, waiting for Oren, scrolling through the news—and then the world shifted. In an instant, the trip we had so carefully planned became an afterthought. By the time Oren joined me at the table, all I could think about was home, and whether our babies were safe.

The next day, our return flights were canceled, and the peaceful gravel roads of Tuscany gave way to hours of logistics, messages, and updates. Getting home became its own kind of adventure, full of stress and uncertainty. We were lucky—we managed to catch one of the last Turkish Airlines flights into Tel Aviv.

Looking back now, it’s hard to untangle the beauty of the ride from the chaos that followed. But maybe that’s the nature of life—joy and worry, adventure and responsibility, all woven together in ways we can’t predict. Our tour through Tuscany’s hills and white roads remains vivid: the silence of the gravel, the golden light on the brown fields, the feeling of being entirely present in each moment. And then, just as sharply, the reminder that some moments pull us out of ourselves, back to where we’re needed most.

Still, I’m grateful for the time we had. Even if we didn’t finish the journey as planned, we carried something real with us—a memory of freedom, of motion, of Tuscany’s quiet magic—into the days that came next.