Tuscany cycling holidays: Taking Italy up a gear

Chianti is well known for wine, but its hills are being discovered by cyclists too

Pit stop: Ellie Ross admires the view

Beneath a dappled canopy, the forest was almost eerie in its stillness. Then I pushed down on my pedals and my surroundings burst into life. Like a headstrong stallion, my bike raced away with me, down a rocky slope riddled with ruts and loose gravel as my clammy fingers clamped the handlebars in an attempt to control my metal steed. We dodged a pheasant and splashed through a stream before the front wheel skidded over a chalky boulder and the bike bucked me off.

"Tutto bene?" a voice shouted from below. Through a cloud of dust, I made out Paolo Cioni, a blur of black and red Lycra with calf muscles like watermelons. Brushing myself off, I extracted a thorn from underneath a fingernail. "Tutto bene," I replied as I pushed my sunglasses on to my nose and heaved myself back on the bike.

I had come to Chianti to test out what could be its best-kept secret: mountain-biking routes. Wedged between Florence and Siena, the region is famed for its vineyard-cloaked hills, but it's also an off-road cyclist's playground. Through vines and olive groves to woodland and unpaved strade bianchi (white roads), the terrain is laced with trails for most abilities. The trouble is, most of us off-roaders don't know where to find them.

Seeking them out is now possible through the villa rental company To Tuscany. Although the trails have long been ridden by locals, they are unmarked. To Tuscany's owner, Sean Caulfield, a keen cyclist, intends to spend the winter marking out beginner, intermediate and advanced routes using GPS with the help of local enthusiasts, including Paolo. From February, the routes will feature on a dedicated cycling page on the To Tuscany website, through which clients can already arrange to hire bikes and guides from approved local suppliers.

"The mountain-biking trails allow you to see Chianti from a different angle," Caulfield told me. "People like Paolo grew up riding them and are now queuing up to guide them."

La Stalla

The rising hills on the two-hour drive east from Pisa airport had made it immediately clear I would be in for some challenging riding. Happily my villa, La Stalla – a beautifully converted stone stable in the hamlet of Montebuoni – eased me in gently. From my bedroom window, row upon row of vines, heavy with purple fruit, stretched out, soaking up autumn's last rays in a sky that was the colour of glowing coals.

I spent the evening prior to the ride fuelling up at Casanuova di Ama, a family-run wine and olive-oil farm, a 10-minute walk from the villa. Between laying out plates of prosciutto and pecorino, owner Daniella Bencini poured generous glasses of white Mattutino table wine, red Vespero made with the sangiovese grapes grown on the hills in front of us, and potent grappa. "In my family, the most important things to have on the table are good bread, good wine and extra virgin olive oil," she said, drizzling her liquid gold over bruschetta.

The next morning, I freewheeled down to Lecchi in Chianti to meet Paolo, who had agreed to guide me along one of the trails. To Tuscany will put guests who are keen to follow these routes in touch with local guides with a similar depth of knowledge. Within a few minutes of setting off on our four-hour ride, we reached a gate separating a vineyard from woodland.

"To keep the wild boar out," Paolo explained, lifting the latch and pushing open the barrier. "They like to suck the juice from the grapes but it destroys the harvest." There are plans to reintroduce wolves to the area to keep their numbers in check.

We weaved our way up through dense oak forest, reaching a gravelly strade bianchi, flanked by cypress trees, standing to attention as though guarding one of Tuscany's most valuable treasures. We pedalled past a handful of tourists at the Castello di Brolio, the birthplace of Chianti Classico and the centrepiece of frequent tussles between the Florentines and Sienese. Along with the two other castles we would pass on our route, Cacchiano and Tornano, it was used as a watchtower when the two cities were at war.

Then began some punishing uphill climbing. Sweat stung my eyes and my lungs gasped for air as I ground through my gears behind Paolo. Just when my thighs couldn't take another revolution, I looked up to find the trail had led us to a medieval hamlet, Monti in Chianti.

We refilled our water bottles at a fountain in the square before pressing on uphill – at my lowest moment, on foot. We paused for respite at Chianti Sculpture Park where my favourite installation was Peperoni, a pair of oversized red and yellow peppers by Piero Giadrossi, the park's curator.

For the remainder of the ride, the only traffic we encountered was a few tractors ferrying batches of freshly picked grapes to the numerous Chianti wineries. After four hours' cycling, I finally spotted the cluster of stone villas and apartments – including a cellar dating back to the 1500s and a private chapel – that form the hamlet of Montebuoni, signalling the end of our 33km loop. It had been exhausting on the way up and terrifying on the way down, but I had emerged exhilarated, if a little saddle-sore and bruised.

As I brushed the Tuscan dust off my legs and waved goodbye to Paolo, a golden light dipped below sunbaked slopes of unexplored trails. I could see a return visit on the horizon.

Travel essentials

Getting there

Ellie Ross was a guest of To Tuscany, British Airways and Carrentals .co.uk. BA (0844 493 0787; ba.com) flies to Pisa from Heathrow from £91 return and Gatwick from £77 return. The price-comparison site Carrentals.co.uk features car hire from Pisa airport from around £13 per day.

Staying there

To Tuscany (0121 286 7782; to-tuscany.com) offers rental of La Stalla at Montebuoni, near Lecchi in Chianti – a two-bedroom, two-bathroom villa with a shared pool from £478 per week.

More information

To Tuscany can arrange cycle hire from €20 per day and guiding services on request. Wine-tasting can be arranged through To Tuscany from €25 per adult.