Tuscany, and particularly the Chianti area, is rich in traditions and events that repeat every year. Here is a calendar of the main cultural, sporting, and gastronomic events you can experience during your stay, within approximately 60-70 km from B&B La Finestra sul Chianti.
Non-competitive vintage cycling race on white roads, famous worldwide for its atmosphere and breathtaking landscape. Participants use vintage bikes and clothing.
Period: First weekend of October
Gaiole in Chianti
Distance: Approximately 15 km
L'Eroica Official Website
Famous horse race of medieval origin held twice a year in the splendid Piazza del Campo, an unmissable event for its intensity and tradition.
Period: July 2nd (Palio di Provenzano) and August 16th (Palio dell'Assunta)
Piazza del Campo, Siena
Distance: Approximately 20 km
Palio di Siena Official Website
Amateur cycling race on some of the gravel sections (white roads) of the famous professional race. An epic experience in the heart of Tuscany.
Period: Early March
Siena
Distance: Approximately 20 km
Gran Fondo Strade Bianche Official Website
Trail running race that winds along the paths and white roads of Chianti Classico, offering breathtaking routes for runners of all levels.
Period: March
Radda in Chianti
Distance: Approximately 10 km
Chianti Ultra Trail Official Website
Event dedicated to gravel bikes, with non-competitive routes through the iconic white roads of Chianti, among vineyards and historic villages.
Period: September
Gaiole in Chianti
Distance: Approximately 15 km
Chianti Gravel Info
Running race offering different distances (marathon, half marathon, 10 km) on a panoramic route among the vineyards and olive groves of Chianti.
Period: June
Castelnuovo Berardenga
Distance: Approximately 10 km
Chianti Classico Marathon Official Website
Annual gathering of vintage motorcycles that attracts enthusiasts and curious onlookers, with exhibitions and tours through the Chianti hills. A dive into motorcycling's past.
Period: May
Castellina in Chianti
Distance: Approximately 10 km
Municipality Website (for local info)
Annual preview of the new vintages of Chianti Classico, Chianti Classico Riserva, and Gran Selezione. An unmissable event for wine lovers.
Period: February (variable date)
Florence (Stazione Leopolda)
Distance: Approximately 45 km
Chianti Classico Official Website
The oldest and largest Italian antiques fair, held monthly in Piazza Grande and the streets of Arezzo's historic center.
Period: First weekend of every month (Saturday and Sunday)
Piazza Grande, Arezzo
Distance: Approximately 60 km
Antiques Fair Official Website
Important summer jazz music festival and seminar with concerts and masterclasses by internationally renowned artists.
Period: July / August
Siena
Distance: Approximately 20 km
Siena Jazz Official Website
Historical re-enactment of Siena's medieval Great Market, with typical products, handicrafts, and shows in the charming Piazza del Campo.
Period: First weekend of December
Piazza del Campo, Siena
Distance: Approximately 20 km
More information
Medieval festival that enlivens the fortified village of Monteriggioni with historical re-enactments, shows, music, and crafts. One of the oldest and most evocative Italian medieval festivals.
Period: July
Monteriggioni
Distance: Approximately 25 km
Monteriggioni Medieval Official Website
Spectacular and bloody historical re-enactment of an ancient Florentine "game," with a tournament between the city's four quarters. Culminates in the final on June 24th.
Period: June (final on the 24th)
Piazza Santa Croce, Florence
Distance: Approximately 45 km
Calcio Storico Fiorentino Official Website
One of the oldest and most prestigious European festivals dedicated to opera, ballet, and symphonic music, with a rich calendar of performances.
Period: May - June
Teatro del Maggio Musicale Fiorentino, Florence
Distance: Approximately 45 km
Maggio Musicale Official Website
Festival combining Brunello di Montalcino wine tasting with high-level jazz concerts, in a suggestive setting.
Period: July
Fortress of Montalcino
Distance: Approximately 55 km
Jazz & Wine Official Website
Initiative taking place throughout Italy, including the province of Arezzo, where participating B&Bs offer hospitality in exchange for services, products, or intellectual works.
Period: Late September / Early October (variable date)
Various structures in the province of Arezzo
Distance: Variable (up to 60-70 km)
Settimana del Baratto Official Website
Spectacular medieval historical re-enactment in which knights challenge each other to hit the "Buratto" (a dummy representing the Saracen), with great participation from the city.
Period: Third Saturday of June and first Saturday of September
Piazza Grande, Arezzo
Distance: Approximately 60 km
Giostra del Saracino Official Website
Multidisciplinary festival that combines music, literature, art, and cultural meetings in one of Tuscany's most fascinating cities.
Period: July / August
Cortona
Distance: Approximately 75 km (slightly beyond the range, but of great importance)
Cortona Mix Festival Official Website
Historic covered market where you can find leather products, souvenirs, and handicrafts. Although not strictly an "event," it's a daily and historic attraction worth mentioning for typical shopping.
Period: All year round
Piazza del Mercato Nuovo, Florence
Distance: Approximately 45 km
More information
Traditional fair with food stands offering typical Tuscan cuisine, music, and entertainment. Ideal for savoring local flavors.
Period: August
Pianella, Castelnuovo Berardenga
Distance: Approximately 8 km
Municipality Website (for local info)
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