1 Feb Traditions Carnevale di Foiano Italy's oldest carnival featuring elaborate floats, parades, and traditional festivities. Foiano della Chiana 1 Feb - 1 Mar 2026 22 Mar Traditions Palio dei Somari Traditional donkey race accompanied by medieval pageantry and festive community events. Torrita di Siena 22 Mar 2026 21 Mar Food & Drink Truffle Festival Spring truffle fair with tastings, local products, and truffle hunting events. San Giovanni d'Asso 21-22 Mar 2026 28 Mar Food & Drink Sagra delle Frittelle Festival celebrating traditional rice fritters with local food and festivities. Cavriglia 28 Mar - 1 Apr 2026 5 Apr Traditions Easter Processions Traditional Easter processions with hooded participants, torches, and solemn religious statues. Castiglion Fiorentino 5-6 Apr 2026 2 May Food & Drink Valdichiana Wine Festival Wine tastings, music, and local food in a beautiful historic setting. Castiglion Fiorentino 2-3 May 2026 30 May Traditions Maggiolata Lucignanese Flower-filled parade with music, floats, and community celebrations to welcome spring. Lucignano 30 and 31 May, 6 and 7 Jun 2026 6 Jun Food & Drink Sagre della Miseria Celebration of Tuscan peasant cooking with simple, traditional, and flavorful dishes. Colle di Val d'Elsa 6-28 Jun 2026 6 Jun Traditions Palio dei Somari Notturno Traditional nighttime donkey race accompanied by medieval pageantry and festive community events. Torrita di Siena 6 Jun 2026 7 Jun Traditions Giostra dell'Archidado Medieval crossbow tournament with costumed parades, flag-throwers, and historical pageantry. Cortona 7 Jun 2026 14 Jun Traditions Palio dei Rioni Annual horse race where town districts compete, preceded by medieval parades and festivities. Castiglion Fiorentino 14 Jun 2026 20 Jun Traditions Giostra del Saracino (night edition) Medieval jousting tournament where Arezzo's four districts compete in Piazza Grande. Arezzo 20 Jun 2026 25 Jun Music & Arts Torrita Blues Festival Annual blues festival featuring international artists in a charming medieval town. Torrita di Siena 25-27 Jun 2026 26 Jun Music & Arts Tria Turris Medieval-themed festival featuring street performances, historical reenactments, and traditional cuisine. Chiusi 26-28 Jun 2026 16 Jul Music & Arts Cortona on the Move International photography festival showcasing contemporary works, exhibitions, and workshops. Cortona 16 Jul - 1 Nov 2026 16 Jul Music & Arts Incantaborgo Street arts festival with performances, live music, and local crafts throughout the historic center. Sinalunga 16-19 Jul 2026 16 Jul Music & Arts Di Giovedí Weekly events in the historic town cenre. It's where Lucignano comes together. Lucignano 16 Jul - 6 Aug 2026 13 Aug Food & Drink Vintage Festival Four-day festival celebrating 1950s and 1960s culture with live music, dance, and vintage markets. Castiglion Fiorentino 13-18 Aug 2026 15 Aug Traditions Giostra del Saracino Traditional jousting tournament where the town's five districts compete in medieval-style games, featuring historical parades and festivities. Sarteano 15 Aug 2026 16 Aug Traditions Palio di San Cassiano Wacky and fun village games including the famous frog-in-a-wheelbarrow race. San Casciano 16 Aug 2026 30 Aug Traditions Bravìo delle Botti Historic barrel race through town streets with parades, music, and medieval flair. Montepulciano 30 Aug 2026 6 Sep Food & Drink Fiera del Cacio Celebration of pecorino cheese with tastings, games, parades, and local traditions. Pienza 6 Sep 2026 6 Sep Traditions Giostra del Saracino (day edition) Medieval jousting tournament where Arezzo's four districts compete in Piazza Grande. Arezzo 6 Sep 2026 16 Sep Music & Arts Lucignano Music Festival World-class chamber music in a medieval hilltown, where art, history, and passion meet. Lucignano 16-20 Sep 2026 26 Sep Food & Drink Festa dell'Uva e del Vino Chiusi's annual wine festival featuring tastings, local cuisine, and cultural events. Chiusi 26-28 Sep 2026 Book your stay at Casale delle Luci
