Leaving Lucca meant we officially started our exploration of the small medieval towns of Tuscany. The majority of our travels occurred throughout the Tuscan province of Sienna. These drives had to be some of our most scenic, taking us through rolling hills, vineyards, and roads lined with cypress trees. There were endless stops for photos and views, and every town seemed more picturesque than the last. First on the list: San Gimignano.
San Gimignano
Driving through Tuscany, you can recognize San Gimignano along the horizon with its numerous towers, giving it the nickname of “Manhattan of the Middle Ages”. As a UNESCO World Heritage Site, the town is recognized for its well preserved and authentic medieval architecture.
Strolling through the pleasant little town allows you to admire 14 of its remaining towers – the number used to be up at a staggering 72!
Volterra
I would like to tell you lots about Volterra, but I ended up taking a nap in the car while everyone else explored because first trimester pregnancy just wears you down sometimes!
Montepulciano
Another lovely town, Montepulciano sits on high ridge of limestone with views of the Val d’Orcia and Val di Chiana valleys below. Strolling through the town provides beautiful views of the countryside from every corner.
The town is known for its main square (the Piazza Grande) and its two famous wines: Vino Nobile di Montepulciano and Rosso di Montepulciano.
Val d’Orcia
The quintessential and most photographed area of Tuscany is the Val d’Orcia: a rural region in southern Tuscany which is a UNESCO World Heritage site. Though it is known for towns like Montalcino and Pienza, just the drive through the countryside is one of the most beautiful and charming in Italy.
There are endless drive-by sites to see here, like Chapel of the Madonna di Vitaleta (lonely but lovely chapel in the countryside), Agriturismo Baccoleno (the Cypress lined road surrounded by flower fields), and the Cipressi di San Quirico d’Orcia (ring of Cypress trees).
