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Our Favorite Festivals in Tuscany

Posted by Carol Sicbaldi

Most people don't realize that in Tuscany, the ancient folk traditions illustrated through festivals, fiere or sagre often represent factual events that carry great meaning for a particular city or village. The locals feel incredibly strong sentiments, emotions, and dedication to these traditions. Here are just a few of our favorite Tuscan Festivals.


March Truffle Party, Certaldo


The Sagra del Tartufo Marzuolo is celebrated in March for three consecutive weekends in Certaldo, Tuscany. The famous truffle and food festival takes truffle tasting to a new level; imagine tasting endless bites of dishes prepared with truffles? To name a few: crostini al tartufo, crostini di polenta al tartufo, tagliolini al tartufo, ravioli al tartufo, nodino di vitello al tartufo, uova al tegamino al tartufo, tagliata del tartufaio, artista tartufata. Are you over-truffled, yet? The Marzuolo—called marzuolo because Italian for March is marzo—is a dark truffle normally only found during this month and is the reason March is dedicated to lovers of this precious tuber! This festa also includes a delightful variety of arts and crafts and an antique market.

Spring Concerts In Florence

From the end of April to the end of June, the Maggio Musicale Fiorentino in Florence features a variety of highly acclaimed international artists performing classical music concerts, opera, and ballet. There are also other events organized in various theaters and locations around the city.

La Giostra del Saracino, Arezzo


Arezzo Giostra del Saracino (Joust of the Saracen) is held twice a year. In 2018, the dates are June 23 and September 3. This tournament has its origins in the early 16th century and commemorates Christian efforts to hold back the tide of Islam in the 14th century. Costumed participants form a lively, colorful procession, which is followed by the main event in which eight elaborately costumed knights charge towards a wooden representation of the Saracen, aiming to hit the Saracen's shield with lances. The Saracen is mounted on a swivel so that part of the task of the knight is to avoid being struck back. Each pair of knights represents one of Arezzo's four rival districts and their supporters each occupy a side of the piazza. The winner receives a golden lance.

Wine In Radda in Chianti

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A very exciting wine event called Radda nel Bicchiere happens in the very sweet Chianti village of Radda–one of our stays on the Heart of Tuscany bike tour. This year, the event falls on May 26-27, 2018. Radda nel Bicchiere is an event offered to locals and tourists alike. You grab a beautifully engraved crystal wine glass on one side of town and merrily make your way across the village tasting wines from 20+ of the region's best winemakers.

Open Cellars: Cin Cin! (Cheers!)

Open cellars is kind of like open bar. The concept is the same. The last weekend in May is dedicated to wine. Cantine aperte is when all wine producers, not only in Tuscany–but all over Italy–open their wine cellars to the general public and offer special tastings with food, music, and other special events to lure folks to their winery. This is an amazing weekend, not to be missed. Believe me!

On June 15, 16 and 17, 2018, in San Gimignano, you can experience the Ferie delle MessiEvery year, San Gimignano commemorates this fertility festival dating back to 1255. People from the four contrade (neighborhoods) of the city—San Giovanni, San Matteo, Castello and Piazza—compete against each other in traditional games in honor of fertility. The hope is to obtain abundant harvests of crops through singing, dancing, and playing medieval games such as tug of war, archery, and the "Giostra dei Bastioni," where the knights battle each other on horses.


That Crazy Horse Race In Siena

Of course, we cannot forget to  mention the famous horse race, Il Palio di Sienaa highlight of summer with year-round preparation. The event features an historical and passionate horse race around the famous main square "Piazza del Campo" in Siena. Incredible!


Photo: Phil Melia

Il Palio is held twice each year, on July 2 and August 16. Ten horses and riders, bareback and dressed in the appropriate colors, represent ten of the seventeen contrade, or city neighborhoods/districts. The Palio held in July is named Palio di Provenzano, in honor of the Madonna of Provenzano, a Marian devotion particular to Siena which developed around an icon from the Terzo Camollia. The Palio held in August is named Palio dell'Assunta, in honour of the Assumption of Mary.
A pageant, the Corteo Storico, precedes the race, which attracts visitors and spectators from around the world.
The race itself, in which the jockeys ride bareback, circles the Piazza del Campo, on which a thick layer of dirt has been laid. The race is run for three laps of the piazza and usually lasts no more than 90 seconds. It is common for a few of the jockeys to be thrown off their horses while making the treacherous turns in the piazza, and indeed, it is not unusual to see unmounted horses finishing the race without their jockeys. The neighborhoods of the city (contrade) race to win "il Drappellone" or the Palio dedicated to the Virgin Mary.

Our Two Most Favorite Tuscan Wheat Festivals


Near Arezzo, and not too far from the area we cycle on our Assaggo Toscana bike tour, there is a delightful festival that takes place in the tiny village of Ruscello called Sagra dell’Occio e Dei Maccheroni al Sugo. Get your goose cooked in an array of scrumptious sauces at this food festival combined with historical reenactment of wheat threshing.

Rievocazione_Storica_della_Mietitura_e_Trebbiatura_del_Grano_Ruscello-950108-edited.jpgPhoto: Renato Marinai Archives

One of our most favorite organic wineries located in in Panzano in Chianti also does a steller reenactment and festival celebrating the wheat harvest as it was done, once upon a time. Battitura del Grano happens at Renzo Marinai Winery in July.

Legends & Miracles in Leonardo's Town, Vinci

In Vinci, the birthplace of Leonardo de Vinci, on the last Sunday of July, there is the Volo di Cecco Santi. This festival includes an historical procession, competitions, games, arts and craft exhibitions, and tastings of local food–not only to celebrate the great genius himself but also to reenact a legendary event: the flight of Cecco Saints. According to popular tradition, Cecco Santi was a captain of the army of Vinci, who for the love of a noblewoman betrayed his city and was sentenced to being thrown from the tower of the Castle of the Counts Guidi, pardoning him only if he managed to escape. As a last wish, he asked to drink a glass of good Vinci wine and ... the miracle happened! Thrown from the tower, Cecco was able to fly up the hill opposite the castle and lived. So it was that in that year the farmers had abundant crops of grapes, olives, and wheat. This tradition is performed by the local people every year and followed by a great celebration.

Giants and Jesters in Volterra


Volterra A.D. 1398 On the 3rd and 4th Sunday in August, the city is animated by fiery war-horses, fearless knights, giants (yes, giants!) noblemen, extravagant ladies, artisans and merchants, common people and peasants, flag-wavers and crossbowmen, musicians and jesters. Magically and creatively, the town of Volterra gathers to take you back in time to the mysterious Middle Ages. This is by far, the best medieval festival I have attended in my almost 20 years in Italy. The best part? For a minimal fee, you can rent a medieval costume from the city hall so you blend in with the crowd.

Barrels of Laughs in Montepulciano

Il Bravio della Botti takes place the last Sunday in August in Montepulciano and is an enjoyable and amusing race that involves pushing wine barrels through the narrow streets of the town. The barrels, each weighing 80 kilograms, are pushed by two athletes from each district/neighborhood. The so-called “spingitori” (pushers), push the barrels along an uphill slope and through the fascinating and gorgeous roads of the historical center. The arrival of the Barrel Race is, as usual, at the doorstep of the Cathedral in Piazza Grande.

Bravio-delle-Botti.jpgPhoto: Proloco Montepuliciano


Who Rolled the Cheese?

September is the time of the grape harvest, more truffle festivals, chestnuts and wild boar. This is a time to discover Chianti and its many world famous wine producers.

Pienza, another stop on our Heart of Tuscany and Tuscany Green bike tours, hosts the Pecorino Cheese Festival. On the first Sunday in September, the capital of pecorino cheese becomes a hub of colour and aromas. While they are rolling barrels in Montepulciano, local Pienza residents are rolling pecorino cheese rounds during the famous game il Cacio al Fuso. First, the younger cheese rollers will take their shot at rolling the cheese as close as possible to the wooden cane in the middle of the square. Next, the older experts will have a try. Why? This fun peasant tradition was a countryside pastime, a game that each family would play in their backyards. The cheese is firm and smooth, so rolling it at a certain angle to make it reach a specific point is not easy!



Last year, I attended this event for the first time. The town’s six districts (contrade) compete for the prize (palio). The oldest player was Armando (90 years old). All participants get three chances to get the cheese closest to it’s target. The top contestant from each contrada then compete against each other to determine the winner who will claim the glory and gain points for their contrada. The historical center of the town was buzzing with food and wine shops and booths bursting with locally made products. The fair ends with a dance in the main piazza, which I happily attended. 
And, of course, I danced with Armando...under the Tuscan moon.


Me with 90-year old legendary Pienza village bike mechanic, Armando

Celebrating The Quintessential Renaissance Man: Boccaccio


October is time for the Boccaccescaa thriving celebration of local food in the narrow streets of Certaldo with food stands, tastings and even cooking lessons. Not only does the festival offer food and wine but also cooking competitions and demonstrations by famous Italian chefs. For three days, the hometown of Giovanni Boccaccio, author of the famous “Decameron”–a collection of novellas celebrating pleasant and happy life according to the humanistic ideals–will host various food and wine events.

Hunting Season Has Ended. Festa Anyone?

On the last Sunday of October, we find falconry, archery, and endless food and wine in Montalcino at the Sagra del Tordawhich re-enacts a competition to celebrate the end of the hunting season.

Bring On The Roasted Chestnuts



On November 1st, local Tuscans living near the dominating Mount Amiata—seen from many of our rides on several of our Tuscan bike tours—come together for a lovely ancient festival called Il CrastoneThis fantastic festival takes place in Piancastagnaio, a village on Mount Amiata where they celebrate the gathering of the chestnuts and all things made with chestnut flour or chestnuts raw, roasted, whole, cooked and boiled.

Doesn't Tuscany sound like a magical place to visit? Join us on one of our upcoming bike tours and get to experience this breathtaking region for yourself.

 Heart of Tuscany

Assaggio Toscana

Tuscany Green



Written by Carol Sicbaldi

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