Visit Tuscany, the official website for tourism in Tuscany, offers useful suggestions for your holidays.
Follow this link to find a selection of cyling itineraries in Florence and its surroundings.
Below our suggested itineraries on Strava, tested and beloved by local cyclists and by customers from all over the world.
1. FROM FLORENCE TO GREVE IN CHIANTI: AMONG OLIVE GROVES, VINEYARDS, AND TRADITIONS
The route starts from the heart of Florence, with a stop at Piazzale Michelangelo for a breathtaking view of the city. Then you leave city traffic behind to enter the peaceful roads of Chianti, among neat olive groves and gentle hills dotted with Chianti Classico vineyards. Midway, Impruneta welcomes you with its historic production of extra virgin olive oil and handcrafted terracotta. Arrival in Greve in Chianti is a delight: the central square is perfect for a break or to visit the tourist office. The return is flat and safe, ideal for a relaxing finish.
2. IN THE HEART OF CHIANTI: SUGAME AND LA PANCA
This variation of the classic route is perfect for those wanting to challenge themselves with a tougher elevation gain. After crossing the gentle Chianti hills, you climb towards Passo del Sugame and La Panca, offering spectacular views and a challenge for cycling enthusiasts. An itinerary that combines the beauty of the Tuscan landscape with a more intense experience, ideal for those who love long rides enjoying every climb and every view.
3. GREVE, MONTEFIORALLE, AND SAN CASCIANO: INCREDIBLE CHIANTI VIEWS
This alternative route is a challenge for more trained cyclists, with demanding climbs and significant elevation gain. The effort is well rewarded by spectacular panoramas and an immersion in often wild and untouched nature. The return from Chiesanuova follows quiet roads, perfect for enjoying the ride, but the last stretch at Le Gore requires attention: a steep, winding, and two-way descent.
4. FROM FLORENCE TO SIENA: AN ADVENTURE WITH TRAIN RETURN
The route from Florence to Siena along SR222 crosses the splendid Chianti hills, with spectacular views of vineyards, olive groves, and historic villages. The road, with little traffic and very scenic, is ideal for a ride immersed in nature. It is suitable for well-prepared cyclists. At the end, you can comfortably return by train from Siena to Florence, combining sport and convenience. An experience that merges scenic beauty and practicality.
5. THE VINCI ROUTE: FOLLOWING LEONARDO’S FOOTSTEPS AMONG HILLS AND CLIMBS
A long and challenging route west of Florence, through hills of rare beauty. The route crosses typically Tuscan landscapes, with climbs that test even the most experienced cyclists. Ideal for those seeking a challenge immersed in nature, with the opportunity to visit Vinci, Leonardo’s birthplace, rich in charm and history. Not suitable for beginners, but perfect for those wanting to combine sport and culture in one itinerary.
6. . THE CHIANTI LOOP: A JOURNEY THROUGH HISTORIC HILLTOPS
The route begins by leaving the vibrant energy of Florence’s Piazzale behind, descending toward Tavarnuzze. This initial stretch serves as a warm-up, though it requires some focus due to local commuter traffic.
As you push forward toward Greve in Chianti, the valley opens up into the iconic scenery of the Gallo Nero region, where rows of vineyards define the hillsides. The real challenge starts here: the climb toward Piazza and San Donato demands steady athletic preparation and the right gearing, but it rewards you with quieter roads and a true sense of immersion in the Tuscan countryside.
Once you reach the ridge, the path levels out toward San Casciano, offering a spectacular panoramic balcony with views stretching across the Val di Pesa.
The final leg of the journey is a swift, technical descent toward Falciani, providing a bit of adrenaline before the terrain flattens out for the return to the city. It is a comprehensive loop, perfect for those with a decent level of fitness who want to experience the seamless transition from Florence’s monuments to the rustic peace of the Chianti hills.
7. VINEYARDS AND OLIVE GROVES CIRCUIT
The route starts from Florence and heads toward Tavarnuzze, a flat stretch to find your rhythm despite the suburban traffic. The road then climbs gently toward Passo dei Pecorai, a steady ascent into a rural landscape of vineyards and small farms.
Reaching Chiocchio, you hit the loop’s highest point—a scenic ridge with breathtaking views leading into Strada in Chianti. From here, a fast descent opens up through vast olive groves, though traffic increases as you approach the city. The final leg follows the plain to Ponte a San Niccolò for a relaxed finish along the Arno. This ride is ideal for moderate fitness, offering manageable climbs and a beautiful transition from the Chianti countryside back to the gates of Florence.
8. POGGIO ALLA CROCE: THE BALCONY OVER VALDARNO AND CHIANTI
The route leaves Florence heading toward Bagno a Ripoli, a flat and often busy stretch that serves as a warm-up before the climb toward San Donato in Collina. After passing Brollo, the road steepens as it winds up toward Poggio alla Croce, the tour’s highest point: a natural balcony offering breathtaking views suspended between the Valdarno valley and the Chianti hills.
The effort of the climb is rewarded by a technical, verdant descent toward San Polo in Chianti, where the landscape softens into rows of vines and dense woodlands. Continuing toward Grassina, the road follows the rolling hills in a pleasant series of ups and downs before re-entering the city through the suburban plain, where traffic becomes more noticeable. This itinerary requires solid athletic preparation due to the concentrated elevation gain in the central section, making it ideal for those seeking a rideable but intense challenge in a wild and evocative setting just outside Florence.