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.
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)!
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.
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!
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.
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.