While in Tuscany, you should pick your itinerary quite carefully: trying to squeeze too much in your stay may be your biggest mistake, as you will be rushing from place to place without being able to actually see or savour anything at all.
Considering Cortona or San Gimignano as your starting point, you should then pick the two or three towns located around it which you would love to visit.
Here is our own advice!
1. Montepulciano and Montalcino
Located 66 kilometres from Siena, Montepulciano is nestled between the Val D’Orcia and the Val di Chiana. Montepulciano is a medieval village known worldwide for being the “jewel of the 1500s” due to its impressive Renaissance art and architecture. It is also famous for its Vino Nobile, as well as other local specialties.
The main square is called Piazza Grande and boasts the great tower and Gothic façade of the Palazzo Comunale (Town Hall) and the Cathedral of Santa Maria Assunta, which dates back to 1619. Don’t miss the view of the Tuscan countryside with the beautiful church of the Madonna di San Biagio.
The hill town of Montalcino, completely encircled by fortified walls, is located in the Val d’Orcia, a few kilometres from Pienza and the Crete Senesi, not far from Monte Amiata. It has remained basically unchanged over the centuries, with its 13th-century defensive walls and its historical centre dominated by the 14th-century fortress.
You can visit the neoclassical-style cathedral dedicated to San Salvatore and Montalcino main square with the Town Hall and a few cafes, bar and restaurants.
Food, romantic landscapes and wine. Montepulciano and Montalcino are the areas where the famous Brunello is made, so do not forget to do also some wine tasting!
2. Pienza and San Quirico d'Orcia
Pienza is a small town situated in the Val d’Orcia, about 50 kilometres away from Siena. Pienza was rebuilt according to humanist urban reorganisation and was viewed as an example for many other Italian and European cities. Piazza Pio II, taking its name from the Pope who was born here, is the hub of Pienza since all of the town’s main monuments are located in this square: the cathedral tower, the Palazzo Piccolomini, and the Palazzo Borgia.
In addition, the town was named an UNESCO World Heritage Site in 1996. Another local quirk is the love-themed street names: you’ll find a Via dell’Amore (love street) and Via del Bacio (kiss street), for example.
San Quirico is a walled village situated in the Val d’Orcia, about 35 kilometres southeast of Siena. Here you can visit the Collegiate church of San Quirico, the Horti Leonini gardens and the church of Santa Maria Assunta along the Via Francigena.
There are many places that are worth a visit in the surrounding area as well, such as the green countryside and the Chapel of Madonna di Vitaleta.
Volterra is one of the oldest towns in the region of Tuscany, it is located in the east side of the province of Pisa, on the borderline of the province of Siena, and is situated on a hill 1770 feet above the sea level, between the valleys of Cecina and Dell'Era. Its origins date back to the ancient Etruscans, who used to call the city as Velathri or Felathri, while the actual name comes from Volaterrae, dating back to the Roman era. The Etruscan walls are still visible, well preserved and surround the city centre.
Furthermore, you can really feel a medieval atmosphere when walking through the narrow streets of the centre. Throughout the Middle Ages, the city was home to the bishop, then it fell into the hands of Florence (and the Medici family), and, afterwards, under the Grand Duchy of Tuscany.
Due to its ancient origins and its excellent condition, there are many things not to be missed. The heart of the medieval town is Piazza dei Priori with the wonderful Palazzo dei Priori, which today hosts the city hall. In the same square you will also find Palazzo Pretorio. A few metres from this square you’ll find the Duomo, a Romanesque Cathedral with its Baptistery. Visit also the Roman Amphitheatre constructed in the 1st century BC as well as the Roman baths and the remains of a Roman forum. Don’t forget to take in the sights of the Guarnacci Museum.
Facts about San Gimignano
San Gimignano is located about 40 kilometres away from Siena, and is a walled village that UNESCO designated a World Heritage Site in 1990.
Known as the Town of Fine Towers, San Gimignano is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls, form "an unforgettable skyline".
It flourished in the thirteenth and fourteenth centuries and used to boast 72 towers, which is why it is also known as the “Manhattan of the Middle Ages”. 13 towers still stand today. You can climb the Torre Grossa and visit its Civic Museum; you can visit the Collegiata (Romanesque former cathedral), the Church of Sant’Agostino with a wonderful 15th-century fresco cycle by Benozzo Gozzoli and, if you are brave enough, the torture museum.
Despite being such a small town, its charms are well known around the world and that is why many tourists choose it as their main destination as they travel to Tuscany or even to Italy.
There is food to be tried, Chianti wine to be tasted, olive oil to be savoured, rolling hills to be walked on, activities to do and events to take part in.
It will be a wonderful experience, which will prove unforgettable for the whole family.