Has anyone been / hosted a wedding in the Tuscan hill towns and can recommend their favorite venues or towns? Needs to accommodate ~50 guests.
Also, any thoughts on outdoor setting in May vs. June? We last went in Aug, so blue skies and no rain which was great. But not sure about Spring weather...
Here's a link that should help you decide on what month to plan a wedding: https://www.ricksteves.com/europe/italy/best-time-to-go-to-tuscany
Is that for this summer?
Next year (2022)
My wife and I got married at Villa Pitiana July 1, 2019. A little outside Florence. We would have preferred May, but wanted to be sure kids were out of school so families could come. We had exactly 50 guests. It was very hot, high 90sF, but otherwise fantastic. We had cocktail hour outside, but dinner inside due to heat. In May or June, you should be able to have everything outside if that's the plan. Feel free to send private message if you'd like more information.
Assuming you're from North America, are you thinking your 50 guests would be able to travel internationally without significant restrictions or boggling expense by spring of 2022? That seems to me a larger uncertainty than the weather - which would be perfect the third week of May.
Do you have a preference of location in Tuscany?
Here's a list of wedding venues, that includes all types, from farmhouse to castles and everything in between.
https://www.weddingvenuesintuscany.com/Wedding-venues-in-Tuscany-1.htm