Hello all and thank you for your input.
We are in the initial planning stages of a 3 week Italy trip (June 2027) and are looking at Arezzo as a three-night stop. We choose it as a stopover as it's between Perugia (where we'll spend 3 nights -- our daughter was there for a study abroad and wants to show us around) and Florence (where we'll spend 5 nights). This stop is planned as a bit of a respite, time to sleep in, maybe do something like a cooking class, catch up on work etc. Coincidentally, we are looking at being there during the June jousting tournament, which sounds like great fun. I'm wondering if the town will be a madhouse all weekend long, or if it's just the night of the tournament.
Piazza Grande will have lots of people on that day, but that weekend will not be as crowded as Florence on any average day in June.