Stradling, a ridge between the Chiana and Orcia Valleys, the Tuscan hill town of Montepulciano, offers visitors sweeping vistas, rustic Tuscan food and world-class wine...it's all vino & vistas
Sitting on a 2,000-foot limestone ridge near the Umbrian border, Montepulciano was said to have been founded by an Etruscan king in the 4th century BCE. The city grew in Roman times increasing in importance and has been ruled alternately by Siena and Florence over the centuries, with each ruling city leaving their distinct marks on Montepulciano. The Middle Ages saw constant fighting amongst Montepulciano's noble families until the Del Pecora family, who had ties to Santa Margherita of Cortona, became the rulers in 1390.
Montepulciano is around 70 km south of Siena, 124 km south of Florence, 186 km north of Rome, but just a half-hour drive from my VBRO rental villa in Cortona. In fact, I can see the lights of Montepulciano each night from the terraced yard that overlooks the beautiful Val di Chiana. Montepulciano is easy to navigate, the newer part of town is at the bottom of the hill full of gift shops, gelaterias and restaurants gearing towards the tourist hoards. The real treasure of Montepulciano is at the top of the hill where the historical center hides a fortress, the Duomo and palazzos for days...
The inviting castle is the very top of town. Constructed in the 1200s on top of Roman ruins, the Fortezza is Montepulciano's art and cultural centre, hosting all sorts of exhibits and events for locals and tourists alike.
Entering the main square, Piazza Grande, one can't help but notice this Piazza feels somehow familiar.
This central square is dominated by the Palazzo Comunale, which looks very similar to the Palazzo Vecchio in Florence. Florence ruled this hill town in the middle ages, and Piazza Grande is covered with the Medici coat of arms showing that Montepulciano was aligned with Florence's power & wealth. The town is absolutely gorgeous, with endless views of the Tuscan countryside. I can see why Montepulciano was the Renaissance stomping grounds for the Florentine elite.
Look for the Pozzo or well in Piazza Grande. Beneath it is a giant cistern that held water for all the surrounding palaces. Above the well are two lions, the symbol of the powerful Medici family of Florence. The lions hold up the Medici coat of arms, kind of like a paid political advertisement of the Middle Ages~ "This clean water brought to you by The Medici Family...you're welcome."

This central square is dominated by the Palazzo Comunale, which looks very similar to the Palazzo Vecchio in Florence. Florence ruled this hill town in the middle ages, and Piazza Grande is covered with the Medici coat of arms showing that Montepulciano was aligned with Florence's power & wealth. The town is absolutely gorgeous, with endless views of the Tuscan countryside. I can see why Montepulciano was the Renaissance stomping grounds for the Florentine elite.
Look for the Pozzo or well in Piazza Grande. Beneath it is a giant cistern that held water for all the surrounding palaces. Above the well are two lions, the symbol of the powerful Medici family of Florence. The lions hold up the Medici coat of arms, kind of like a paid political advertisement of the Middle Ages~ "This clean water brought to you by The Medici Family...you're welcome."
For 360 degree views of the Tuscan countryside, a trip up the tower of Palazzo Comunale is a must. To climb the tower, head into the palazzo and up the stairs on the left. On the second floor is the cashier office (open 10am-6pm) and it a €5 entrance fee. From the top of the tower, Montepulciano flows down the hill like a silk veil into the lush Tuscan farmland- so breathtakingly beautiful. You also get views of the square below with Palazzo de' Nobili-Tarugi in its arcaded Renaissance splendor, the Duomo with its unfinished facade, Palazzo Contucci. The Contucci palace was built by del Pecora family whose son hid Saint Margherita of Cortona away as his mistress, and is surrounded by many other stunning Renaissance palaces in the Piazza.
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| Photo of San Biagio by Klaus Stebani |
From your perch on the top of the tower, you can see the domed church on San Biagio below. This domed masterpiece was the work of Renaissance artist Antonio da Sangallo who also designed Palazzo Tarugi. Both of these elegant buildings are built out of locally quarried travertine marble. Bramante, the master architect, spent time in Montepulciano, and the dome of San Biagio influenced his design of St. Peter's dome at the Vatican. A walk down to San Biagio along Via di San Biagio from San Francesco church is a delightful stroll.
Behind the altar of the church is a three-panel retable by Sienese early Renaissance artist Taddeo di Bartolo. Painted in 1401, this altarpiece includes a self-portrait of the artist as one of the apostles. This panel was painted in-situ, which means this work of art is displayed in the place that it was intended to for-not a museum. It's my favourite way to appreciate the art the way the artist intended it to be experienced.
Other treasures in Montepulciano must be experienced, but not of the visual sense...
| Corso of Montepulciano |
Whether you are a wine connoisseur, an architecture devotee or just like beautiful scenery, Montepulciano has it all!

