Many Central Tuscan hill towns like Volterra, Casole d'Elsa, San Gimignano and Monteriggioni have impressive full costumed re-enactments of former glory days.
While the particular history of the town may be different, to celebrate it there will likely be competitions between athletes or flag bearers of the town quarters, roving minstrels and nimble dancers or artisans selling their crafted wares. There will most assuredly be long outdoor tables and plentiful food.
Some to keep a look-out for are:
Volterra AD 1398, with a crossbow competition, procession of the nobility, falconry, dancing – (3rd & 4thSundays of August)
Ferie Messum of San Gimignano– a fertility or harvest festival with 4 town quarters competing in games of tug of war, archery and cane warfare (3rdweekend in June)
And should you decide to spend the Christmas or New Year holidays in Tuscany
Presepe Vivente of Casole d'Elsa - In this case it's not medieval Italy, but ancient Bethlehem which is brought to life, with costumed towns people exhibiting the the timeless crafts that are still practiced in Tuscany.