Events and Activities to do in Chianti

Events and Activities to do in Chianti

Chianti is well known for its rich history, fascinating culture, and historical traditions, but there are also endless opportunities to explore and discover a wide variety of events and activities within this stunning region. Immerse yourself in medieval festivals, experience the thrill of a vintage bike race, or indulge in wine-related events guaranteed to excite your senses. Our hand-picked selection of the best events and activities in Chianti will take you on an unforgettable journey, helping you uncover the best the region offers.

L’Eroica: A Vintage Bike Race

vintage bicycles, close up

L'Eroica is a unique cycling event born in 1997 in Gaiole in Chianti, and it combines challenging routes (hence the name, the Italian for “heroic”), magnificent Tuscan landscapes, and a love for vintage. In fact, all the participants ride vintage bikes and wear old fashion garments accordingly.

It is inspired by Coppi and Bartali, two of the greatest Italian cyclists, who had a heroic approach to sport and life. In addition to his legendary career - and rivalry with Coppi - Bartali is also known for playing an active role in helping the Jewish community during WW2, carrying documents and passport photos inside the bicycle frame, to help Jewish refugees escape.

From the original event in Gaiole, Eroica has grown into a global movement, a network of events attracting tens of thousands of cyclists and fans of all ages around the world. It has become a real lifestyle for locals and tourists alike.

Ferie Messum: A Mediaeval Festival

Ferie Messum, or Ferie delle Messi, was a medieval celebration of the fertility of the lands and of the new harvest. The tradition dates back to the 13th century, and has been revisited in recent years. Ferie Messum is held in the historic centre of San Gimignano, on the 3rd weekend of June.

The event is organised by I Cavalieri di Santa Fina, and it is centred on the re-enactment of the chivalric tradition, inspired by the battles of Montaperti (1260) and Capaldino (1289), of which we can read in ancient documents.

There are also many events, like live music, shows, and games, but the most important one is the adrenaline-filled Giostra dei Bastoni, the traditional knight’s tournament. During the Giostra, the city’s four "Contrade" (neighbourhoods) - San Giovanni, San Matteo, Castello, and Piazza - compete against each other, just like they used to during the Medieval Times.

Expo del Chianti Classico - Wine Festival

people toasting, glasses of red wine

Chianti Classico Expo is held in Greve in Chianti, usually during the second week of September. On the beautiful square of Greve, tourists and wine lovers can find different stalls where the most important wine producers present their labels. This is a unique opportunity to get to know Chianti Classico wine in its production area.

Aside from experiences organised with the winemakers during the festival - like tastings and presentations - there will also be many artistic and cultural events related to the local and rural traditions.

Chianti Festival - Music, Theatre, and Arts Festival

The Chianti Festival takes place in July and is the most important music and theatre event in Chianti. This itinerant event travels through the Municipality of Castelnuovo Berardenga, Gaiole in Chianti, and Castellina in Chianti and is organised in collaboration with Fondazione Toscana Spettacolo.

The shows program changes every year and has already given stage to famous national and international artists like Richard Galliano, Linsday Kemp, Luciana Savignano, Stefano Bollani, Davide Riondino, Alessandro Benvenuti, Gene Gnocchi and Dario Vergassola.

Calici di Stelle: Wines and Stars

Calici di stelle is an event dedicated to wine that takes place throughout Italy - and, of course, also in Chianti - during the nights of the  first two weeks of August. There are lots of wine producers participating, and they all organise wine tastings, cellar tours, concerts, and cultural events. The program changes every year and is usually published on the Movimento del Vino website.

Markets in Chianti

Open-air Italian food market

Markets are a great way to get to know a place, its culture and day-to-day rhythm. Italian markets are usually crowded, noisy and beautifully chaotic, almost like a microcosm within the cities. They are usually a great place to taste and buy local products, and if you like a bargain this is the place for you. Let’s dive into the best markets in the Chianti area.

The first mention goes to Wednesday’s market in Siena, one of the biggest in Tuscany. This is held every Wednesday around the majestic walls of the Medici Fortress, from 8 am until 1.30 pm. The range of products is vast from food to garments, and household items, and the atmosphere is cheerful and lively.
On the 3rd weekend of each month, in Piazza del Mercato, the Antique Market of Siena takes place, which is also worth a visit.

Greve in Chianti
The weekly market in Greve is held every Saturday morning from 8 am until 1.00 pm. On the  4th Sunday - in Piazza Giacomo Matteotti, from 9 am to 6 pm - there is also Il Pagliaio Market, where you can find farmers with fresh, local and seasonal products, as well as artisans working with traditional and natural materials.
From June to August, on the 3rd Thursday of each month, in Greve in Chianti the Stelle e Mercanti will also take place. At this evening market - open from 6 pm till 11 pm, you will find food vendors and local artisans; This is not only a market but more of an event, as the program also comprehends music and entertainment.
Finally, on the first Wednesday of September, there is the Fiera Annuale, with food and local artisans.

Castellina in Chianti
In Castellina, the weekly market is held every Saturday morning, from 8 am to 1 pm, in Via IV Novembre.

Radda in Chianti
The market in Radda in Chianti takes place on the 4th Monday of each month, from 3 pm to 8 pm, in Piazza IV Novembre.

Panzano’s weekly market is on Sunday mornings, from 8 am to 1 pm.
Furthermore,  on the first Sunday of the month, the Aprilante Market takes place. On this occasion, over 100 stalls animate the village, and you can find local artisans and producers offering the best quality organic products and antiquity vendors.

Gaiole in Chianti
In Gaiole, there is only one monthly market, held on the 2nd Monday of every month from 2 pm to 8 pm, except for the month of September, when the market happens on the first Monday.

Whether you like historical revisitation or hunting for the best bargain, you have plenty of options in Chianti. If you would like to know more about the area, read our Chianti Travel Guide and start planning your vacation.

And if you are still looking for villas to rent in Chianti, visit our catalogue and find the right one for you.

If you need help planning your vacation or have any questions about Tuscany villas to rent, please don’t hesitate to contact us.

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