San Gimignano, Italy

San Gimignano was somewhat of a "whistle stop" on our way from Sienna to Livorno during our trip to Italy (Click here to view the trip overview page).
This Piazza (image above), entered from Via San Giovanni, is the main square of the town. It is triangular in shape and is surrounded by medieval houses of different dates, among them some fine examples of Romanesque and Gothic palazzos. At the centre of the piazza stands a well which was the main source of water for the town\'s residents. The structure dates from 1346. Although much of it has been renewed in the late 20th century, parts of the paving date from the 13th century.

Only a 42 kilometer drive from Siena (via Raccordo Autostradale Firenze & SR68/SP44). We had read about this area and Castel San Gimignano during our Italy trip research phase, and decided that since it was on the way to Livorno, that this would be a good place to visit to break up the drive, explore the village and maybe have a bite to eat.

First View of San Gimignano

These are the kinds of views of the village that we got as we drove up on the Italian SP1 highway (Via San Gimignano), surrounded by miles of lush agriculture, trees and a surprising lack of traffic.

It is only a 55 kilometer drive from Siena to San Gimignano, but the route was so scenic & traffic free, that it did not feel like we had driven very far at all.

Exploration of San Gimignano

San Gimignano is a charming walled medieval hill town located in the province of Siena, Tuscany, in north-central Italy. Known as the "Town of Fine Towers," it is celebrated for its remarkably preserved medieval architecture and the unique skyline created by its iconic tower houses.

During the town’s height in the 12th and 13th centuries, wealthy families constructed more than 70 towers as symbols of their power and influence. While only 14 towers remain today, they continue to dominate the landscape, offering visitors a glimpse into the town’s prosperous past. The tallest of these towers, the Torre Grossa, stands at 54 meters and is open to visitors, providing breathtaking panoramic views of the surrounding Tuscan countryside.

San Gimignano’s cobblestone streets, stone buildings, and picturesque piazzas transport visitors back in time. Its well-preserved walls, dating back to the 13th century, enclose a town filled with historic landmarks, including Piazza della Cisterna, Collegiata di Santa Maria Assunta, and several museums. Recognized as a UNESCO World Heritage Site, San Gimignano is a must-visit destination for those seeking to experience the rich history, art, and culture of Tuscany.

Surrounded by rolling hills carpeted in vibrant green, San Gimignano stands as a testament to Tuscany's idyllic beauty. Surrounded by fertile farmlands and sprawling vineyards, this medieval gem is renowned for its exceptional white wine, Vernaccia di San Gimignano. Crafted from the ancient Vernaccia grape, this esteemed wine boasts a unique minerality and refreshing acidity, a reflection of the terroir where it thrives. Grown on the sun-drenched sandstone hillsides that embrace the village, the Vernaccia grape flourishes in this microclimate, producing grapes that are bursting with character. A sip of Vernaccia di San Gimignano is an invitation to savor the essence of this captivating region, a journey through the senses that celebrates the harmonious interplay of nature and human craftsmanship.

Exploration of San Gimignano

Since San Gimignano is somewhat of a "living museum", the streets are narrow and cobble stoned as originally constructed. Within the walls, the well-preserved buildings include notable examples of both Romanesque and Gothic architecture, with outstanding examples of secular buildings as well as churches. The Palazzo Comunale, the Collegiate Church and Church of Sant' Agostino contain frescos, including cycles dating from the 14th and 15th centuries.

San Gimignano is primarily pedestrian-only, so no need for dodging cars or buses! However it should be noted that walking on cobblestone can be very tiring if you do not have good shoes on!

Collegiate Church of San Gimignano

The Collegiate Church of San Gimignano, also known as the Basilica of Santa Maria Assunta, is a stunning Romanesque church. This UNESCO World Heritage Site is famed for its richly decorated frescoes and historical significance.

Built in the 12th century, the church’s modest exterior contrasts with its breathtaking interior, which is adorned with vibrant fresco cycles painted by renowned artists of the time, including Bartolo di Fredi, Domenico Ghirlandaio, and Benozzo Gozzoli. These frescoes depict scenes from both the Old and New Testaments, covering the walls in intricate detail that illustrates Biblical stories for worshippers of medieval San Gimignano.

One of the church’s highlights is the Last Judgment fresco by Taddeo di Bartolo, which portrays vivid scenes of heaven and hell in dramatic, colorful detail. The church also features a wooden crucifix attributed to Niccolò di Segna and a striking chapel dedicated to Santa Fina, a local saint, adorned with frescoes by Ghirlandaio that depict her life and miracles.

San Gimignano Town Hall

The town hall building is immediately to the left of the Collegiate Church (the Duomo).

The Palazzo Comunale also known as the Palazzo del Popolo of San Gimignano has been the seat of the civic authority in the comune since the 13th century. It is located on the Piazza del Duomo adjacent to the Collegiate Church of the Assumption of the Blessed Virgin Mary. The building and Collegiate Church are at the heart of the medieval town, and are part of the UNESCO World Heritage Site of the "Historic Centre of San Gimignano".

San Gimignano is headed by a mayor (sindaco) assisted by a legislative body, the consiglio comunale, and an executive body, the giunta comunale. Since 1995 the mayor and members of the consiglio comunale are directly elected together by resident citizens, while from 1945 to 1995 the mayor was chosen by the legislative body.

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• The creation of some portions of this page's narrative text were assisted by OpenAI. (2025). ChatGPT [Large language model].