May is a vibrant time in Tuscany and Umbria, with the countryside in full bloom and a calendar packed with cultural, gastronomic, and historical events. Whether you’re a local or a traveler seeking authentic Italian experiences, here’s a curated list of must-attend events this May 2025.

1. Coppa della Perugina – Perugia (May 8–11, 2025)

A historic car race that brings vintage vehicles to the streets of Perugia, celebrating the city’s automotive heritage.

More info: https://www.coppadellaperugina.com/en/

2. Calendimaggio – Assisi (May 7–10, 2025)

A medieval festival featuring parades, music, and competitions between the city’s districts, celebrating the arrival of spring.

More info: https://www.calendimaggiodiassisi.com/

3. Festa dei Ceri – Gubbio (May 15, 2025)

A centuries-old tradition where teams race through the streets carrying large wooden structures topped with saints’ statues.

More info: https://www.umbriatourism.it/en/-/festa-dei-ceri-event

4. Cantine Aperte – Various Locations (May 24–25, 2025)

Wineries across Tuscany and Umbria open their doors for tastings, tours, and special events celebrating local wine culture.

More info: https://movimentoturismovino.it/cantine-aperte-movimento/

5. Maggio Musicale Fiorentino – Florence (April–June 2025)

An annual arts festival showcasing opera, concerts, and ballet performances in various venues throughout Florence.

More info: https://www.maggiofiorentino.com/en/

6. Radda nel Bicchiere – Radda in Chianti (May 20–21, 2025)

A wine-tasting event in the heart of Chianti, offering samples from local producers and pairing with traditional foods.

More info: https://www.raddanelbicchiere.net/

7. Mostra Mercato dell’Artigianato – Anghiari (April 25–May 1, 2025)

A market exhibition showcasing traditional crafts, with artisans demonstrating their skills in the medieval town of Anghiari.

More info: https://www.mostramercatodellartigianato.it/

8. May in Castiglion Fiorentino. 30 days of wines, music and events!

May in Tuscany and Umbria offers a rich tapestry of events that celebrate the regions’ history, culture, and gastronomy. Whether you’re indulging in local wines, witnessing historical reenactments, or strolling through flower-adorned streets, there’s something for everyone to enjoy.