fb track
Foggy countryside around Certaldo at dawn

A car ride from Florence to Siena

Get ready to enjoy wonderful landscapes, historical hamlets and the tasty specialties along the way

First stop
San Casciano in Val di Pesa
San Casciano Val di Pesa
San Casciano Val di Pesa - Credit: APT

The first town we come across on the itinerary is San Casciano in Val di Pesa, 15 kilometres southwest of Florence. The town is perched on a hill and its territory teems with picturesque parish churches and castles.

Check out the Pieve of San Pancrazio, Pieve of Santo Stefano, Pieve of Santa Cecilia and Pieve of San Giovanni in Sugana. Also, don't miss the castles of Bibbione, Gabbiano, Pergolato and Montefiridolfi.

An interesting fact: in 1513 the Italian writer and politician Niccolò Machiavelli was exiled in a hamlet near San Casciano and wrote The Prince and The Mandrake there.

Second stop
Tavarnelle Val di Pesa

Carrying on along the Val di Pesa road you'll come across Tavarnelle Val di Pesa. Its main sights are mostly religious buildings like the Badia di Passignano and the Romanesque Pieve of San Pietro in Bossolo.

Another attraction of this town are the surrounding vineyards, you'll notice them for sure (and you'll love them)!


Third stop
- Credit: Bernardo Conde

It's time to make a little detour and head west to Certaldo. Located 35 kilometres southwest of Florence, Certaldo is full of history since it was the hometown of Giovanni Boccaccio, the famous Renaissance author who penned The Decameron. In fact, one of the main attractions is Boccaccio’s former house.

Also take a look at the Palazzo Pretorio or Vicariale, an imposing residence belonging to the Florentine governing magistrates, built in the early 12th century and rebuilt in the 15th century. It is also the highest building in Certaldo, overlooking the whole town.

During the summer, Certaldo hosts an event called Mercantia, a festival brimming with theatre, music, magicians and dance performances.

Fourth stop
San Gimignano
San Gimignano
San Gimignano - Credit: C. D'Aliasi

Now let's move on to San Gimignano, the quintessential medieval hilltown where 14 stony medieval towers stand out.

The historical centre of San Gimignano is a UNESCO World Heritage Site: the well-preserved buildings boasting both Romanesque and Gothic architecture and other notable buildings and churches prove this.

Friendly tip: check out the Vernaccia di San Gimignano Wine Experience museum and... don't forget to taste some good wine!

Fifth stop
Colle Val d'Elsa
UMOCA Colle Val d'Elsa
UMOCA Colle Val d'Elsa

Now it’s the turn of Colle Val d'Elsa, internationally renowned for the production of crystal glassware. Speaking of which, one of the must-sees in town certainly is the Crystal museum.

Colle Val d'Elsa also has a long history, especially in the part called “Colle Alta”, the oldest part of the town. Here you can visit the medieval Palazzo del Campana, the Castello, the Duomo, the Palazzo dei Priori and typical workshop and craftshops.

Sixth stop
Walking towards Monteriggioni
Walking towards Monteriggioni - Credit: Kinzica Sorrenti

The last stop of this itinerary before reaching Siena is Monteriggioni, the medieval walled town located on a hilltop set halfway between San Gimignano and Siena.

As you probably know, the town boasts pretty massive walls all around and it is one of the most important stops along the Tuscan stretch of the Via Francigena.

Last but not least, Monteriggioni hosts many important events across the year, such as the Monteriggioni Medieval Festival and the Slow Travel Fest.

Art and Culture
In this area
hotel 97 Accommodation facilities local_offer 16 Deals event 29 Events