Tuscany by motorbike: Chianti and Val di Chiana

Chianti and the Val di Chiana: itinerary and useful advice for a food and wine tour by motorbike to be savored right up to the last bend.

Tuscany - Chianti by motorbike itinerary route motorbike bike information
Chianti Hills

Motorbike itinerary between Florence and Siena for a ride (also by bike) among the hills and olive trees of Chianti and Val di Chiana.

Advice and information for a weekend on the bike between cultural visits and food and wine tours starting from the cradle of the Renaissance up to Montepulciano.

The kilometers are not many, about 300, and in one day they can easily be covered calmly, but we recommend dividing this itinerario more days to be able to visit calmly Firenze and the other places we visited along the way.

Content index

  1. Firenze
  2. Castellina in Chianti
  3. Castelnuovo Berardenga
  4. Montalcino
  5. Montepulciano 
  6. Data Room

Getting lost in the rolling Tuscan hills, in a continuous up and down of emotions and colors: drive in Toscana it is equivalent to driving in a painting.


Chianti Tuscany by motorbike
Chianti Toscana by motorbike – Photo by Rudi Maes

We dedicated a full day to visit Firenze, a city that has kept its charm and splendor of the past unchanged. An enchanting city that never ceases to surprise, with its works of art, churches and architecture that recall its role in the development of Renaissance culture and art. The capital of the Toscana is the starting point of the first stage that takes us through the Chianti along the SR222, called "Chiantigiana“. We drive along a really fun route, between gentle ups and downs and soft curves that hide vineyards and houses expertly built with local stone in a color between beige and grey.

Castellina in Chianti

We reach Greve in Chianti from which the ascent begins Montefioralle, where we park the motorcycle to be able to visit this medieval village located at the top of a hill from where it is possible to admire the Greve valley. Definitely to taste their true and original Florentine. With a full stomach we still descend towards Greve and then drive up to Castellina in Chianti.

Tuscany - Chianti by motorbike itinerary route motorbike bike information San Gimignano
San Gimignano

THE SR222 in this stretch is a beautiful alternation of countryside, woods, small villages and more forest, which in summer is a godsend to have stretches in the shade. Once in Castellina we enjoy this beautiful village with its characteristic shops and streets still immersed in an aura with a medieval flavour. We allow ourselves a detour of about 16 km from the original route to get to Monteriggioni. The road is pure fun for us motorcyclists and the few kilometers go by too quickly and we wish they would never end. And if you want to stretch a few more kilometers, don't forget San Gimignano, one of the most beautiful medieval towns in Tuscany with well 72 towers.

Castelnuovo Berardenga

The second stage takes us along the SR429 before a Radda in Chianti, a small village gathered in medieval walls on a hillock that marks the border between the valley of Weight and valley of Arabia. At Badia a Coltibuono we take the SP408 and after Gaiole in Chianti we turn onto the S484 up to St. Regulus and the famous castle of Brolio, an extraordinary example of turreted architecture, mosaic decorations and Sienese Gothic style. Visited the castle we head to Castelnuovo Berardenga, orange flag of the TCI where another immersion in medieval Tuscany awaits us. Here it is possible to visit the thematic landscape museum and stay overnight near where a village has been converted into a relais. The hamlet of is worth a visit Monteaperti, famous for its thermal sources and theater of the battle between Siena and Florence.


val d'orcia motorbike itinerary tuscany montalcino
Montalcino - Shutterstock

We leave the Chianti region and, through the Crete Senesi, we reach the Wave d'Orcia. From Castelnuovo we take the SS73 and drive up to Siena, heritage ofUnesco, architectural pearl of medieval and Renaissance Italy, famous for its Palio and for the oldest bank in the world still open. For us motorcyclists, the fun begins outside the walls of Siena and more precisely on the route that winds through the Crete Senesi up to Montalcino. A route of 60 km among the most evocative of Tuscany that starts from the S438 up to Asciano to get to Montalcino via the SP451. The landscape and the colors seem painted by nature and lead us not to overdo the gas. We want to enjoy every meter and even manage to add a stop to visit the Benedictine abbey of Mount Oliveto Greater. Continuing we are surrounded by expanses of vineyards, a sign that Montalcino is not far away. We don't shy away from savoring an excellent glass of wine immersed in this almost timeless context.


The last forty kilometers are pure enjoyment for us motorcyclists: the SP146 makes us have a lot of fun. Let's meet Pienza, a locality awarded the orange flag of the TCI, a fifteenth-century city set within its imposing walls. We then come to Montepulciano, Renaissance town, leads to the Val di Chiana.

Montepulciano Tuscany motorcycle bike itinerary - San Biagio
Montepulciano - San Biagio (Ph. Canva)

Worth visiting are the large palaces with high-sounding names such as Sangallo, Baldassarre Peruzzi and churches such as San Biagio, a masterpiece by Antonio da Sangallo the Elder or the church of S. Agostino, a work by Michelozzo. But Montepulciano is not only culture, but also excellent wine such as Nobile, Valdichiana or Rosso Montepulciano. Not to forget the DOP Terre di Siena oil, the Mascina variety plums, the pecorino cheese and the sausages. The tour ends here, with the awareness of those who would never want it to end, and with Tuscany in our hearts, we point the bikes towards home.

Data Room

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