Montepulciano Events and Festivals Calendar 2020

Festivals, theater, and concerts – Montepulciano has too many events to list! The main pillars of life in Montepulciano are the Arts and Culture, and this town knows how to celebrate them.

Each month, there are many events in Montepulciano that must be experienced. The list below contains only a few of our favorites. During your stay at Fonte Martino Guest House & Estate, we will happily update you on current local events.


February Events in Montepulciano

Preview of Vino Nobile di Montepulciano 2020

preview vino nobile wine tastingMontepulciano is home to Vino Nobile…the noble wine. Each year in February, more than 40 local wineries offer a preview of the most recent vintage (2017) of Vino Nobile di Montepulciano. This wine tasting event is now celebrating its 20th year!

Where: Piazza Grande & the Fortress of Montepulciano
When: February 14-16, 2020

Carnival di Montepulciano

Carnival is celebrated in Montepulciano complete with a costume procession through the ancient streets leading to the historic center of town. This event occurs on the Sunday before Mardi Gras.

April Events in Montepulciano

Cioccolando: Chocolate Festival in Montepulciano

cioccolando chocolate festival montepulcianoLove chocolate? Indulge in this amazing chocolate festival with handcrafted chocolates, aperitifs, workshops and guided tastings by expert pastry chefs and chocolatiers.

Where: Piazza Grande & the Fortress of Montepulciano
When: April 4-5, 2020

Gran Fondo New York Italy

gfny-italiaFor the 2nd year in a row, Montepulciano will host the “Gran Fondo New York Italy”. This is an international cycling competition that is 110 km in length and takes place throughout the province of Siena. With more than 1200 participants from all over the world, this is a very competitive and exciting event!

Where: Montepulciano and Torrita di Siena
When: April 3-5, 2020

Easter Festival in Montepulciano

festival di pasqua logoThis annual event celebrating it’s 6th year celebrates the Easter season than with enchanting music concerts held in the picturesque churches and theaters of Montepulciano.

Where: Montepulciano
When: April 11-26, 2020

May Events in Montepulciano

Fiera di Sant’Agnese

Witness this annual historic procession through the ancient streets of Montepulciano in honor of Sant’Agnese.

Cantine Aperte

Held in late May, this weekend event is dedicated to wine. Visit numerous wine cellars, let the winemakers share their secrets, and taste the incredible locally-made wines.

Giostra del Saracino

Held by San Biagio just below the towering town of Montepulciano, this festival includes amazing food and displays throughout the day. In the evening, witness jousting competitions that will remind you of days past.

July Events in Montepulciano

Cantiere Internazionale d’Arte

Montepulciano Cantiere Internazionale d’Arte logoThe prestigious Cantiere Internazionale d’Arte (International Art Workshop) is the spotlight of July. This month-long event is a feast of music, art, theater, and dance. This is not to be missed!

Where: Historic Center of Montepulciano
When: July, 2020

August Events in Montepulciano

Montepulciano Calici di Stelle 2020

montepulciano calici di stelle 2020Calici di Stelle, or “Chalices of  Stars”, is an annual event to celebrate the night of St. Lawrence.  The cobbled streets of Montepulciano will be lined with a market of art and antiques and there will be live concerts under the stars as well as exhibitions by the Flag Throwers and Drummers of Montepulciano.

Where: Piazza Grande, Montepulciano
When: August 10, 2020

Bravio delle Botti – Montepulciano Wine Barrel Race

Bravio delle Botti - Montepulciano Wine Barrel RaceThis amazing festival occurs on the last Sunday in August in honor of the patron saint of Montepulciano, San Giovanni Decollato. The 8 Contrada (districts) of Montepulciano compete by rolling 176 pound wine barrels up the steeply inclined streets. They race to be the first to claim the coveted Bravio, a painted cloth, the pride of their Contrada.

Where: Montepulciano
When: August 30, 2020

September Events in Montepulciano

October Events in Montepulciano

Montepulciano Run

montepulciano run logoThis three-day sporting event takes place at the end of September. There are competitive and non-competitive events for everyone set in the beautiful landscape of the Tuscan countryside.

Where: Montepulciano
When: October 2-4, 2020

Olive Oil and Autumn Flavours Festival

Olive Oil FestivalOctober brings the harvest of oil-rich olives used to make the highest quality extra virgin olive oil. What better way to celebrate the harvest than with the Olive Oil and Autumn Flavours Festival!

Where: Montepulciano
When: October 18, 2020

Christmas Market in Montepulciano

Christmas Village in Montepulciano Tree 2018.jpgStarting late November and lasting through the first week of January, Montepulciano turns into a festive Christmas Market. With the streets lit by endless hanging lights, you will think you stepped back in time. Piazza Grande magically transforms into an outdoor market full of wonderful treasures and delicious treats. Enjoy skating on the ice rink all while being entertained by the angelic carolers, and of course Santa’s Castle shouldn’t be missed!

Where: Montepulciano
When: November 20, 2020 – January 6, 2021
(Every weekend, Weekday Schedule Varies)

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