A car ride from Florence to Siena

Imagine you are in Tuscany and you have already seen all of Florence’s attractions, including the gardens, the Oltrarno and the main museums. Imagine you have a car or you have just rented one. A nice idea for a car ride (or a motorbike trip if you prefer) is to head for Siena, enjoying the wonderful scenery on your way. There are many ways to reach Siena:
  1. one road passes through the Chianti, or Chiantishire;
  2. the fastest way to reach Siena is to pass through San Casciano in Val di Pesa, Tavarnelle in Val di Pesa, Poggibonsi, Colle Val d'Elsa, Monteriggioni and Siena;
  3. the itinerary I recommend passes through many of the places I mentioned in the second route, but with two more places that are well worth seeing: Certaldo and San Gimignano.
Put your key in the ignition and start up the engine.... Let's go!
San Casciano Val di Pesa [Photo Credits: Giuseppe Moscato]
San Casciano Val di Pesa [Photo Credits: Giuseppe Moscato]
The first town we come across on the itinerary is San Casciano in Val di Pesa, 15 kilometres southwest of Florence. Almost entirely destroyed by allied bombardments during the Second World War, San Casciano Val di Pesa was rebuilt and is now renowned for its parish churches and castles. Visit the Pieve of San Pancrazio, Pieve of Santo Stefano, Pieve of Santa Cecilia and Pieve of San Giovanni in Sugana. While we’re on the subject of 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, located 25 kilometres south of Florence. As for San Casciano, Tavarnelle's main sights are 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.
Certaldo [Photo Credits: Francesco Sgroi]
Certaldo [Photo Credits: Francesco Sgroi]
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 actually 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. San Gimignano is a walled town in the province of Siena, located 50 kilometres northwest of Siena. 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. Don't forget to taste some Vernaccia di San Gimignano! ;)
Monteriggioni [Photo Credits: Aldo Cavini Benedetti]
Monteriggioni [Photo Credits: Aldo Cavini Benedetti]
Now it’s the turn of Colle Val d'Elsa, internationally renowned for the production of crystal glassware. 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 on the way before reaching Siena is Monteriggioni, the medieval walled town located on a natural hilltop. To know more about Monteriggioni and its attractions read this post.
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