Siena reflects medieval Tuscany, and its inhabitants pursued their rivalry with Florence even into the realm of urban planning. They preserved their city’s Gothic appearance through the centuries, assimilating between the 12th and 15th centuries.

During the late medieval period, Duccio, the Lorenzetti Brothers, and Simone Martini were to have a significant influence on the course of Italian and, more broadly, European art. The whole city of Siena exists as a work of art that blends seamlessly into the surrounding landscape. In addition to the city’s magnificent historic districts, there are lively streets filled with artisanal boutiques, sweet-smelling patisseries, pastry shops, and tempting restaurants within each ward. A Tuscan itinerary could not perhaps be complete without stopping at this feast for the senses.

As Siena is a large city with many districts, I have summarized this article to focus on the medieval parts of the province with gothic town halls alongside the major wine producers.

SIENA CITY

The orange-red Gothic city is a mix of spiritual and secular monuments that have retained their medieval forms and extraordinary art collections. Il Campo is Siena’s central piazza, famous worldwide for the Palio run, a horse race conducted two times a year. The James Bond movie, Quantum of Solace, features Siena and the Palio. The red Palazzo Pubblico, Museo Civico, and its tower, Torre del Mangia, dominate Il Campo. As with the Duomo, Siena’s cathedral, the Palazzo Pubblico, was also built during the Council of Nine Governors’ rule. Pinacoteca Nazionale, a recently renovated art gallery, houses masterpieces by Duccio, Simone Martini, and others from the 14th century. There are many books in local libraries about Siena and its traditions in most languages. Piccolomini Library is also one place you should not miss. The one-day tour of the city is not enough for you to understand the thorough history of this place.

SAN GIMIGNANO

A hill town in the province of Siena, also known as the “city of fine towers.” The old town centers on Piazza Della Cisterna, surrounded by medieval houses. It has a skyline of medieval towers, including the stone Torre Grossa. I visited this place during the summer before the Pandemic. It is best to arrive before 10:00 a.m. or after 5:00 p.m. if you cannot bear the summer heat. In any case, it is a beautiful historic center with a well-preserved feudal atmosphere. The towers of San Gimignano were not just displays of wealth but also represented the power of the families who built them. So, the taller the towers were, the wealthier the owners appeared to be. Often, this would lead to family feuds lasting for decades and division of loyalties among citizens. Legends tell stories of young lovers from quarreling families who would meet in secret, in the shadows of the towers, like real-life Romeos and Juliets. In the nearby green Tuscan farmland, towering medieval ramparts rise imposingly and provide first-time visitors with unforgettable scenery. Once inside, the town is easy to navigate, with narrow streets leading to squares containing churches, palaces, and unavoidable towers.

MONTEPULCIANO

In the Italian province of Siena, Montepulciano is another medieval and Renaissance hill town and commune. The region is known for its food and drink production. Montepulciano consists of vineyards and is known for its red wine, Vino Nobile. Visitors to the town have increased substantially since the Twilight movie New Moon premiered. The ancient city of Montepulciano is full of lavish Renaissance palaces, old cathedrals, charming squares, and secret little corners that boast stunning views of the beautiful Val d’Orcia and Val di Chiana valleys that surround it.
If you visit this town, you should also see the rest of Val d’Orcia. I have posted a separate article on Val d’Orcia, another province of Siena.  You can read my post where I share a funny incident over Gladiator Avenue.

CHIANTI

Chianti is known for its wine, not just good wine but excellent wine. The region roughly extends to the two central provinces, Siena and Florence, with a combination of perfect weather and soil that produces the world’s best wine. The cultivation of vines in Chianti dates back to the Etruscans who inhabited the area before the Roman Empire. Many will recognize the straw-covered bottles as being a classic symbol for the Chianti wines; however, these bottles are rarely ever used unless perhaps the winemaker is making a vintage style. Visiting Chianti generally does not have a set season. Both summers and winters are great times to visit this small town for exciting wine-tasting events. Despite not being a wine expert, I could tell the smoothness of Chianti wine from other Italian wines that go well with authentic Italian food, something with a tomato base.