Maggio Castiglionese

In May, Castiglion Fiorentino dazzles with the shine of a village festival and the understated elegance of a Tuscan jewel. Its piazzas, alleys and districts become spaces for sharing and discovery. Each day is an invitation to live, rather than just visit.

For four weeks, the village lights up with art exhibitions, a sampling and agricultural and food fair, solemn celebrations dedicated to patron saint San Michele, along with sporting events and competitions involving the entire village. The first beloved village food fairs and district festivals lead up to the highly anticipated Palio dei Rioni in June. There’s the blue-and-white Medieval Festival of Cassero, the traditional Medieval Banquet of Porta Fiorentina and the elegant Vicolo DiVino of Porta Romana, amid tastings and music under the stars.

Among the innovations of the 2025 edition of Maggio Castiglionese are: 

• The new Primi di Maggio food festival with an entire tasting village where you can savor eight iconic pasta dishes, prepared live by talented chefs together with local restaurants, along with Pasta Toscana, an experience to be enjoyed with all senses exalted by music, workshops and cooking shows;
• APERIEXPO, an initiative linking art with good food on May 1, 4, 9 and 11, from 6:00 pm to 9:00 pm, in the Cassero area, with an exhibition of artworks and a Made in Tuscany aperitif.

There is also much anticipation for the third edition of the Valdichiana Wine Festival, hosted in the beautiful setting of the Cloister of San Francesco, as an opportunity to discover the best wines of the area and selected Italian excellences.

For those who love photography, the Castiglion Fiorentino Photo Fest also returns as an space open to emerging and professional photographers. A festival designed to exalt talent, tell stories through images and promote a visual culture accessible to all.