A historic and charming town, Montepulciano is set atop a hillside in the Tuscan countryside. Surrounded by fourteenth-century medieval walls, the town is steeped in medieval and Renaissance history that travelers can experience by strolling the car-free streets, exploring the city’s churches and palazzi, enjoying the Tuscan views, and indulging in delicious cuisine and locally-produced wine.

FESTIVALS & EVENTS

Montepulciano embraces its history by hosting a variety of events and festivals, many of which take place in the city’s main square, Piazza Grande.

Each year, the city holds the Bruscello Festival, an outdoor play that is based in medieval and Renaissance themes. The show depicts the city’s history and is performed by locals, not professional actors.

Also reminiscent of the city’s medieval days is the Bravio delle Botti, a wine barrel race between the town’s eight districts that runs through the city streets to reach Piazza Grande. The event also features an opening parade with hundreds of locals dressed in historic costumes.

Piazza Grande also hosts the Cantiere Internazionale d’Arte, or International Arts Workshop, each year in July. The event is one of the most prestigious arts festivals, featuring theatrical, operatic, musical, and dance performances.

Montepulciano’s Carnival, held annually in February or March, includes a processional, shows for children, and many elaborate costumes.

Other events throughout the year in Montepulciano include an annual wine event known as Anteprima Vino Nobile, a sweets and chocolate fair called Cioccolano, an Easter festival, harvest season festivals, and a Christmas Village event during the holiday season.

OUTDOOR ACTIVITIES

The best way to experience the beauty and history of Montepulciano is to explore the city on foot while soaking up the Tuscan sun.

Walking down the city’s main street and throughout the historic part of town, travelers will discover a series of elegant palaces, including Palazzo Cervini, Palazzo Avignonesi, Palazzo Comunale, Palazzo Contucci, Palazzo Tarugi, and more.

The main square, known as Piazza Grande (though its official name is Piazza Vittorio Emanuele) is a central hub of Montepulciano at which travelers can engage with the local culture and experience many of the city’s most important buildings, including some of the historic palaces.

To take in the views of the surrounding countryside, travelers can climb to the top of the Palazzo Comunale’s tower and see panoramic Tuscan views. On clear days, the view expands as far as Siena and Mount Cimone.

The thirteenth century Church of Sant’Agostino features the distinct Tower of Pulcinella, which dates back to the sixteenth century. The clock at the top of tower has a statue of Pulcinella, one of the symbols of Naples. Historians are not entirely sure how this statue ended up in Montepulciano, but it is believed that it may have been brought to town by a bishop from Naples. The wood and metal statue is tied to the clock and strikes the bell every hour and every quarter hour.

To relax after a long day of sightseeing, travelers can take a calming soak in Montepulciano’s thermal waters. Known for being incredibly therapeutic and healing, the thermal waters date back to Roman times. Other options such as massages, mud treatments, and more are available.

INDOOR ACTIVITIES

Also in the Piazza Grande is the city’s Duomo. Built between 1592 and 1630, the façade of the Duomo is modest and rustic. The interior features a statue of Bartolomeo Aragazzi, a fifteenth-century altar, and the Madonna of the Pillar painting by Sano di Pietro.

To get out of the elements, Montepulciano has a couple of unique museums to explore.

Inside Palazzo Neri Orselli is the Museo Civico, or Civic Museum. This museum contains a variety of archeological artifacts from the medieval and Renaissance time periods. Many Etruscan and Roman artifacts are found there as well, including art, urns, jewelry, and more.

The Museo della Tortura is not for the faint of heart. Inside travelers will see a variety of torture devices, including beds of nails, thumb screws, guillotines, and more. All of the devices are from dark medieval times.

SHOPPING

Montepulciano’s main street, leading from Porta Al Prato to the Piazza Grande, features a few places for travelers to shop, including small artisan workshops and fashionable boutiques.

However, the most popular item to purchase when visiting Montepulciano is wine. The town is known for its Vino Nobile and many wine shops throughout the city specialize in selling top Montepulciano wines – the perfect souvenir!

FAMILY AND KIDS

For a day trip from Montepulciano that the whole family will enjoy, travelers can visit Chiusi, an important Etruscan and Roman city. Just 13 miles southeast of Montepulciano, Chiusi is home to an abundance of history from the Etruscan time period, including the Museo Nazionale Etrusco (National Etruscan Museum) filled with ancient artifacts ranging from pottery to tombstones. There is no better way for travelers of all ages to learn about this area’s fascinating past.

UNIQUE EXPERIENCES

Just outside of the city’s walls is the fourteenth century, Gothic-style Church of Santa Maria dei Servi. It features a Baroque interior and contains art by the Sienese school. From Santa Maria dei Servi, travelers can look down the hill and see another famous church, the Church of San Biagio.

The church is known for its isolated location in the countryside, making it a pilgrimage destination for many. Built in the early 1500s, it was crafted from gold travertine stone and takes the shape of a Greek cross floorplan. It also features a high dome, sixteenth-century frescoes, and a small museum. It is a must-see site among the trees of the Montepulciano area.

One of the best experiences to be had in Montepulciano is delighting in the delicious, Tuscan-style cuisine and renowned wines. The area is known for its production of impeccable red wine known as Vino Nobile di Montepulciano, and travelers can visit historic wine cellars built beneath the city’s many palazzi. To go alongside the wine, enjoy traditionally rustic and simple, yet flavorful, meals such as pici pasta with wild game sauce.

The hilltop town of Montepulciano is a true delight for all types of travelers. After taking in the historic sites and admiring the town’s art, be sure to set aside ample time for an unforgettable tasting of the area’s legendary Vino Nobile di Montepulciano.