The best things to do in Tuscany and Umbria in May, including popular events, festivals, attractions and tours, free activities and entertainment. See upcoming events and what’s on in Tuscany and Umbria in May..

All May is a great occasion to see the flowering in Castelluccio, Umbria.

  • MAY 3, 4, 5 and 6 CALENDIMAGGIO, in Assisi Info and tickets:

  • May 6 and 7 a wine and street food wine event with music  at the Slow Food awarded winery Madrevite.

  • May 6 and 7 in the historical center –  Arezzo Vintage Market


  • May 13 and 14: Pienza Flower Show
  • May 13 and 14: The Agricoltural festival in Tre Berte, Montepulciano (Not to miss the horse  parade)

  • May 14: the Spring market in Asciano, Siena.
  • May 15:  The Yearly Ceri festival in Gubbio 
  • May 19 to 21:  Waiting for Barbarossa,  at Quartiere Castello with flag-wavers and parades in San Quirico D’Orcia.
  • May 20 and 21 PERUGIA FLOWER FESTIVAL at Barton Park

  • May 19, 20  and 21: Porkettiamo, pork festival at San Terenziano, Perugia.

  • May 19 to 21: the Todi Flower Show


  • May 20 and 21: in Radda in Chianti, the yearly local wine festival



  • May 26 to 28 Sansepolcro Street Food Festival


  • May 27 and 28 –  do not miss the yearly event of CANTINE APERTE, Open cellars in Tuscany and in Umbria.
  • May 27 the Spring MarketMercatino di Primavera a Bagno Vignoni 

More Family experiences at Indiana Park in Chianciano:

When: Each Saturday and Sunday from 10.00 AM to 7.00 PM


Or visit La Foce Gardens, Unesco Patrimonium, visits are every Wednesday and long 50 minutes.


And Each Monday at Il Casale in Pienza: