Biking in Tuscany

A unique and original way to discover Tuscany while keeping yourself fit and active: go cycling around the region and discover its historical towns, quaint villages, evocative valleys, medieval hamlets and monasteries. An unconventional way of travelling!

DAY 1- FLORENCE, VAL D’ELSA AND SAN GIMIGNANO. 26 km. (11 on dirt roads)

In the morning meet Bruno, your MTB guide, at the Bike store in Florence to fix your bike. Train to Castelfiorentino. Ride across the scenic hilly ridges of Val d’Elsa over the typical Tuscan countryside. Visit of St. Gimignano. A possible extra 13 km circular loop across the wine road of the Vernaccia di San Gimignano is available for the most avid bikers. Overnight in San Gimignano .


The parish church of Santa Maria in Chianni, mentioned by the archibishop Sigerico during his trip along the via Francigena at the end of the 10th century.

The Pancole Sanctuary, built in 1670 after an apparition to a young deaf mute girl who was healed.

The Romanesque parish church of Cellole, completed in 1238
The famous Medieval town of San Gimignano, the “city of the beautiful towers”

DAY 2-VAL D’ELSA COUNTRYSIDE 37 km. (18 on dirt roads)

Departure in the morning. Ride on scenic ups and downs across the typical Val d’Elsa countryside, biking across vineyards and olive groves and fording little streams. Overnight in the countryside near Strove.


The Medieval abbey Badia a Coneo, one of the oldest Vallombrosian monasteries, dating back to the 11th century.

Olive groves and vineyards of Tuscany

DAY 3-MONTERIGGIONI AND SIENA 28 km. (18 on dirt roads)

Departure in the morning
Ride towards the fortified town of Monteriggioni (one of the best preserved medieval towns of Italy) passing the imposing Castel Pietraio and the suggestive abbey of Abbadia Isola. Arrival in Siena and visit of the town at leisure. Overnight in Siena


The evocative fortified monastery of Abbadia a Isola, built during the second half of the 10th century, (as indicated in its name – isola means island-), on the edge of a swampy area at the crossroads between Florence, Fiesole, Siena and Volterra

The impressive Medieval fortified town of Monteriggioni, one of the best preserved Medieval hamlets in Italy, mentioned even by Dante in his “Divina Commedia”

The Chiocciola Castle, an important outpost of the Senese during the Middle Ages

The famous Medieval city of Siena with its shell-shaped square and beautiful palaces.

DAY 4-VAL D’ARBIA, BUONCONVENTO 41 km. (31 on dirt roads)

Departure in the morning. Ride among the scenic ridges of Val d’Arbia, following sunny dirt roads and passing the odd fortified granary of Grancia di Cuna. Overnight in Buonconvento a medieval village dating to back to 1100 a.D.


The Medieval fortified granary of Grancia di Cuna
The Medieval village of Buonconvento

DAY 5-VAL D’ORCIA, BAGNO VIGNONI, PIENZA 37 km. (5 on dirt roads)

Ride inside the scenic Val d’Orcia, declared World Heritage Site by U.N.E.S.C.O. in 2004. Visit of the medieval hamlet of San Quirico d’Orcia, the magic thermal town of Bagno Vignoni and its characteristic square built around a huge thermal water pool. Last but not least, explore Pienza, the “Renaissance” city. Overnight in Pienza.


The Medieval town of San Quirico d’Orcia, famous for its most important monument,
the 12th century Collegiata Church
The castle of Vignoni, mentioned since the 11th century
The Medieval thermal town of Bagno Vignoni, whose hot springs have been used since Roman times
Pienza, the earliest example of a Renaissance “ideal town”.

DAY 6-CHIANCIANO TERME AND CHIUSI 39 km. (7 on dirt roads)

Departure in the morning. Ride across the heart of the scenic val d’Orcia. Explore the the medieval fortified hamlet of Monticchiello and the imposing old town of Montepulciano. Ride in the wide Val di Chiana and bike through the Etruscan towns of Chianciano Terme and Chiusi. Overnight in Chiusi or Chianciano.


The medieval hilltown of Monticchiello

The Medieval and Renaissance hill town of Montepulciano, famous for its great Vino Nobile di Montepulciano

The Medieval hilltop town and modern spa resort of Chianciano Terme
The Etruscan town Chiusi, famous for its national museum


Check out. Clients may continue their trip to Rome or Florence from the railway station Chiusi/Chainciano.

The tour includes accommodation on half-board basis; lunches are all on own due to the biking activities


Back to Tours