For many visitors, Tuscany's cycling identity begins and ends with L'Eroica, the vintage-bicycle pilgrimage held each October that has become shorthand for the region's romance with the road: steel frames, wool jerseys, bread and ribollita at the feed stations. Founded in Gaiole in Chianti in 1997, the event celebrates an older, deliberately analogue idea of the sport. But it makes a wider point: cycling in Tuscany rewards those willing to move through it slowly.
Set off along Chianti’s roads and you’ll notice the temperature drops as the route dips into a shaded valley. Dust rises off the strade bianche — the pale, unpaved tracks that thread between the vines. There is rosemary, pine, and, if the timing is right, the sweet, slightly alcoholic smell of grapes fermenting after the harvest. "In a car, Tuscany can feel like a film passing behind a window," says Marco Benfatto, a former professional racer turned cycling guide. "On a bicycle, you are inside the picture."
From 16th to 19th October, Benfatto will lead guests through Chianti as part of Cycling and Stillness, a COMO Journey based at Podere San Filippo, the apartment-style residence on COMO Castello del Nero’s 740-acre estate. Guided rides are balanced with a dedicated day of COMO Shambhala wellness, including yoga, recovery sessions and a 60-minute signature treatment. Guests can choose a road bike or an e-bike, individually fitted before setting off, with a support van shadowing the route for mechanical help and refreshments.
Autumn is Benfatto's favourite season to ride. "It is a particularly beautiful time to experience Tuscany," he says. From Podere San Filippo, the countryside begins almost immediately: vineyards and olive groves, narrow roads and hilltop villages, with no transfer required before the ride can begin.
The emphasis is not on kilometres covered or elevation gained. "Mindful cycling means focusing on presence rather than performance," Benfatto says. Cadence, breathing and effort management — tools he once used to shave seconds off his race times — are repurposed instead to help guests feel "relaxed, comfortable and connected to their surroundings."
The terrain encourages that approach. Tuscany, he says, is a “continuous mosaic of short climbs, challenging little ramps and technical descents”, rewarding rhythm more than outright strength. An optional warm-up ride offers a gentle introduction, particularly for first-time e-bike riders. Benfatto might lead a 45-kilometre loop from Podere San Filippo into the Val di Pesa, followed by a steady four-kilometre climb to the fortified hilltop village of Montefioralle. The reward is coffee in the piazza before the return along quieter back roads.
The following morning, a longer ride heads through the Val d’Elsa towards San Gimignano: a TK-hour excursion across rolling hills, vineyards and quiet country roads, with time to pause and explore before returning to the estate. On the third day, the route turns towards southern Chianti, following scenic, low-traffic roads lined with cypress trees and vineyards, ridden at a steady pace for TK kilometres — around TK hours.
E-bikes, Benfatto says, make these landscapes accessible to riders with very different levels of fitness. “They remove some of the anxiety around Tuscany’s hills without removing the pleasure or satisfaction of cycling.” Couples, families and groups of friends can stay together rather than separating according to ability. “You don’t need to call yourself a cyclist to ride a bicycle in Tuscany,” he adds. “If you know how to ride and enjoy being outdoors, you can experience this.”
For Benfatto, cycling “allows you to understand how closely wine, agriculture, landscape and village life are connected here.” A ride is rarely just a ride; it tends to encompass a mid-ride picnic, or end at a cellar door or village piazza, coffee in hand. The riding is balanced with recovery too. After consecutive days in the saddle, the final day's yoga, guided stretching and wellness treatment at COMO Shambhala help restore flexibility through the hips, release tension across the shoulders, and ensure guests finish the retreat feeling restored rather than depleted.
Benfatto gives his guests the same instruction every day: put the watch away. "What I would want them to remember isn't their speed or how many kilometres we covered," he says. "It would be the quiet roads, the changing light, the clean air, the conversations — and the simple pleasure of moving through Tuscany on two wheels."
The Cycling and Stillness COMO Journey runs from 16th to 19th October at Podere San Filippo. For more information, please contact our concierge or email [email protected].
