Medieval fairs, festivals, culture near Montalto Castle vacation rentals in Tuscany

Fairs, festivals and local culture

While enjoying your villa rental in the medieval castle Montalto in Toscana, you will have plenty of additional opportunities to immerse yourself in the culture of Tuscany and the spirit of medieval times.

The area’s beautiful villages are the perfect setting for numerous Medieval fairs, animated by characters in historical costumes, minstrels and storytellers, wandering musicians, flag throwers and many others simply enjoying the thought of stepping back in time. Some towns have antique fairs or musical events, and there are also many sagre (festivals dedicated to a particular local product), usually starting in early summer and continuing on through the fall when local specialties (truffles, wine, olive oil, chestnuts) come into season. But if you are coming to Tuscany during other periods of the year, don't worry as there is always something to see or do (or eat!) then as well.

Siena's Palio horse race, run twice a year in early July and mid-August, is the most famous local event: the whole town goes wild for three days of celebration, centering on a horse race that is really a war-game, where victory depends on luck, skill and (quite legally) money. But after the Palio we’ve also listed some other ideas for you, roughly organized by the time of year.

Il Palio (Siena)

The Palio is a bare-back horse race that takes place every 2 July and 16 August in Siena’s main square, Piazza del Campo. The town is divided into 17 contrade (neighborhoods), 10 of which take part in each race and compete for a palio (prize) which is a banner dedicated to the Virgin Mary. The square is filled with costumed pageantry involving over 600 participants, and massive feasts are set up on long outdoor tables on the side streets.

The Palio is much more than a simple event for the Sienese — it’s actually a large part of their lives from the time of their birth. Each person belongs to a Contrada and participates in its life and in the organization of the Palio throughout the entire year. The Sienese live the Palio with great passion.

During this special occasion, the ring around the piazza is covered with tufa clay. At around 3 p.m. each Contrada performs a benediction ceremony of its horse in its own chapel, then joins in the large parade in historical costume that winds through the city. The parade arrives in Piazza del Campo around 5 p.m. and ends by around 6.30-7 p.m., after which the race takes place.

You can attend the Palio for free from the center of the Piazza del Campo. You should arrive by at least 4.30 p.m. to find enough space to stand (if you want a prime location along the side of the race track, these spots are taken by morning). More comfortable positions from which to watch the Palio exist around the Piazza and prices vary; contact us if you’d like help in buying tickets in the bleachers or on the private balconies that face onto the Piazza.

Spring Fairs, Festivals and Events

Scoppio del Carro (Florence)

Easter Sunday is celebrated in Florence with the Scoppio del Carro (explosion of the cart), a tradition that dates back to the first Crusade when fire was distributed around the city by a cart at Easter so that families could relight their hearths that they had extinguished on Good Friday. Today, an elaborate wagon built in 1622 and standing two to three stories high is dragged through Florence by a fleet of white oxen decorated in garlands, to the square between the Baptistry and Cathedral. The cart has been rigged with fireworks so that when the colombina (a dove-shaped rocket symbolizing the Holy Spirit) slides down a steel cable at full speed from the Cathedral altar, it will set off a dance of fire on impact. A big bang ensures a good harvest. The Explosion of the Cart takes place around 11 a.m. so watch out for the cart on the streets of Florence an hour beforehand; a parade in medieval costume follows. Explosion of the Cart .

Mercatino delle cose del passato (Greve in Chianti)

Greve in Chianti’s antiques and collectors fair is one of the better antiques fairs in Tuscany and occurs annually on Easter Monday (the name means “little market of things from the past”). On display are old and reproduction rustic furniture, old tools, farmhouse and vineyard artifacts, ceramics, glassware and cutlery, a very good range of embroidered linen, iron work etc. Along the street off the square, porchetta and other snacks are available, together with plenty of pecorino cheese, dried fruit and sweets.

Calendimaggio (Assisi)

Calendimaggio is a three day costume festival that takes place in Assisi on the Thursday, Friday and Saturday after the 1st of May. The upper and lower sectors of Assisi compete against one another in various ancient games and an evening choir competition. There are also daylight and evening costume processions.

Maggio Musicale Fiorentino (Florence)

The May Music Festival in Florence is a series of internationally acclaimed classical music concerts and recitals, opera and ballet in venues across the city. Events often continue into June. Tickets can be hard to come by, so check the schedule online and purchase tickets in advance.

Giostra dell’Archidado (Cortona)

This crossbow competition is held usually the second Sunday in June. A procession of knights on horseback, along with ladies, flag flyers, soldiers, pages, civil and religious authorities, all wearing medieval costumes, parade through Cortona's historic center. The joust commemorates the wedding of Francesco Casali, Lord of Cortona, and the noblewoman Antonia Salimbeni of Siena, which took place in 1397. The crossbowmen from Cortona's five quarters ("quintieri") compete for a golden arrow.

Summer Fairs, Festivals and Events

(Also read about Siena's Palio, above)

Fiera delle Messi and Giostra dei Bastoni (San Gimignano)

The streets and squares of San Gimignano hold a medieval costume festival each year on the third Saturday and Sunday of June. Knights from the four quarters of San Gimignano re-enact the old "Feriae Messium" (harvest festival) tradition, with giostre (jousts) between mounted knights armed with bastoni (wooden lances), and there are food stands offering local gastronomic products including olive oil, wine and saffron together with a large arts and crafts market. The public is entertained during the festivities by minstrels, musicians, street performers and archers, and the winning quarter parades through the city with celebrations continuing into the evening.

Giostra del Saracino (Arezzo)

The Giostra del Saracino (Joust of the Saracen) is held twice a year, at night on the third Saturday in June and then during the day on the first Sunday in September. This tournament has its origins in the early 16 C and commemorates Christian efforts to hold back the tide of Islam in the 14 C. A lively and colourful procession of costumed participants is followed by the main event in which eight costumed knights charge towards a wooden representation of the Saracen, aiming to hit its shield with lances. The Saracen is mounted on a swivel so that part of the knight’s challenge 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.

Calcio Storico (Florence)

Fireworks along the Arno conclude Florence's celebrations to St. John the Baptist, the city's patron saint, on June 24. First, there is a parade in historical costume that starts at the Church of Santa Maria Novella and ends at the Church of Santa Croce, where the Calcio Storico is then played in the dirt-covered square in front of the church. The game is an occasionally violent combination of soccer, rugby, and big time wrestling, all played while wearing 16th century costumes.

Siena Jazz (Siena)

The Medicean Fortress in the center of Siena houses the Siena Jazz School, with courses and concerts all year long and a festival during the month of June. Over a period of two weeks more than 30 concerts and jam sessions are held in the two major town squares, on the terrace in front of the Enoteca, in the gardens of the Contrade clubs, and other locations throughout the town.

Open Air Concerts in San Galgano

The Abbey of San Galgano is the enchanting setting for concerts in collaboration with the Accademia Chigiana music academy in Siena. During the month of July, musical comedies, theatrical performances, grand operas and concerts take place under the stars in the evocative scenario of this roofless cathedral.

Festa Medievale (Monteriggioni)

Monteriggioni’s Medieval Festival takes place on the first and second weekends of July. The festival includes local and also professional performers, music, exhibitions recreating military techniques, daily life and arts and trades, and food stands filling the piazza inside this fortified town.

Bravìo delle Botti (Montepulciano)

This barrel rolling race takes place on the last Sunday in August. The event, which was originally a horse race to celebrate Montepulciano's patron Saint John the Baptist, dates back to 1373; it was abolished in the 17th century but was revived as a barrel race in 1974. Montepulciano’s eight Contrade (town neighbourhoods) compete for a Palio, a painted cloth banner. The barrels weigh 80 kg and have to be rolled uphill about 1800 m along the main street of Montepulciano, finishing in the Piazza Grande. Costume processions precede the competition and a street banquet follows.

Volterra A.D 1398 (Volterra)

This medieval fair takes place each year during the last two Sundays of August, and fills Volterra with mediaeval costumes, events and food — complete with medieval money. Flagwavers, crossbowmen, musicians and jesters provide entertainment, along with fiery warhorses, fearless knights, noblemen, ladies, artisans, merchants and peasants.

Fall Fairs, Festivals and Events

(Also read about Arezzo’s Giostra del Saracino, above)

Cacio al Fuso (Pienza)

Pienza makes among the best pecorino cheese in Italy and a wide range of excellent cheeses is available to be tasted and bought during this fair on the first Sunday in September. The Cacio al Fuso itself is a cheese rolling competition: cacio is the original Tuscan word for pecorino and the fuso or spindle is the target of the game.

Palio della Balestra (Sansepolcro)

This is a crossbow tournament held every year on the second Sunday of September when large numbers of citizens dress in medieval costume. It’s a very ancient competition between the bowmen of Sansepolcro and nearby Gubbio, held in honour of Sant'Egidio (Aegidius), founder and Patron Saint of Sansepolcro.

Rassegna del Chianti Classico (Greve in Chianti)

This showcase for Chianti Classico wines takes place on the second weekend of September and the preceding Thursday and Friday. You purchase a glass (which you can keep) and are then allowed to taste up to eight of the wines offered at the many stands. If you find something you like you can purchase it on the spot.

Festa dell'Uva (Impruneta)

The most popular annual event in Impruneta is the Festa dell’Uva, or Grape Festival, held on last Sunday of September. Over the years it lost some of the original rural characteristics but its essential popular nature has remained intact. The most important part of the parade, which usually starts at 3.30 pm, consists of allegorical carts built by the four districts of Impruneta. Popular dances, performances, tasting of agricultural products and shows of the local handicraft products are held.

Festa dell'Uva (Vagliagli)

The village of Vagliagli near Castelnuovo Berardenga holds this wine festival during the last week of September, with numerous booths for tasting and buying the typical products of this part of Siennese territory and with special attention to the excellent Chianti wine of the area. The parade of allegorical carriages derives its theme from the countryside and the life of the farmers, and is accompanied by local men and women in traditional costumes.

Villaggio della Birra (near Buonconvento)

If beer is more your style, craft beer is the center of attention in Bibbiano, near Siena, for two days around the middle of September. The Villaggio della Birra (Beer Village) offers tastings of artisanal beers (mostly in the Belgian style) along with various meat dishes, porchetta, local cheeses and roasted meats from Siena.

Sagra della bistecca e del fungo porcino (Certaldo)

Certaldo, near Florence, holds its Beef Steak Festival, celebrating the famous fiorentina, every weekend from mid-september to mid-october. The event also celebrates the beginning of the mushrooms season, as mushrooms populate the woods of the Chianti region with the first rainfalls. The traditional dish consists of fried porcini mushrooms and steak strips.

Sagra del Fungo e della Castagna (Vivo d'Orcia)

Vivo d’Orcia is a small village near Castiglione d’Orcia, and it holds its mushroom (fungo) and chestnut (castagna) festival on the second and third weekends of October. The town divides into two teams for the Palio del Boscaiolo: using antique saws, contestants cut logs into stools and tables, where they then eat a polenta dish that the rest of the team has prepared in the meantime. There is a nature walk where mushroom species are explained, but the main attraction is the range of local porcini mushroom dishes available, and the sale of porcini and chestnuts.

Sagra del Tordo (Montalcino)

Montalcino’s feast of the thrush, on the last weekend of October, is quite spectacular, with drum parades and archery trials on Saturday and a popular feast held inside the walls of the castle all day Sunday, with very good food and wine purchasable by the glass. On Sunday morning there is a parade in mediaeval costume, and the main archery contest takes place in the afternoon after another costume procession. Two archers from each of the four quarters of Montalcino compete.

Sagra del Tartufo Bianco (San Miniato)

The Sagra del Tartufo Bianco (white truffle) takes place in San Miniato during the last three weekends in November, with a large offering of truffles and truffle-derived products, wine, pecorino, salami, olive oil, grappa etc. This territory produces 25% of Italy's white truffles and the prices here, while expensive, are as good as you can get — and the truffles are fresh. Truffles don't retain their aroma for more than 2-3 days so enjoy truffle dishes in the restaurants and booths here or take a few home for immediate consumption. There are smaller truffle festivals during October in nearby Corazzano (first weekend of October) and Balconevisi (third weekend of October).

The Tuscany villas for rent in the Castle of Montalto offer a convenient location to visit all the attractions and cities of art.