Oh I know what you mean about the tomatoes! No, my grandma is from the north so it's not the same town... it sounds idyllic though! MH and I like to go up to the Senese for the Terme, especially San Gimignano, which is really close to Poggibonsi. Fun fact, an old friend of mine went to Poggibonsi to give birth in the water. I went up to visit her with another friend and really enjoyed our stay/ [totally random anecdote]
Have so much fun! Maybe we'll cross paths and won't even know it!
Where in the north is your grandma from, DH's father's family is from the north for many generations, always near Milan. I think nonno's father was the first one who was actually born in the city of Milan, generation wise. I think his nonna actually moved to Milan as a girl, keeping the tuscan estate as the summer home.
My friend from Colle Val d'Elsa was born in Poggibonsi. I need to plan a separate trip to visit her at some point. She does food tours and stuff in her area, visiting Cinta Senesa farm, going to markets in all the small towns in that area.
Ugh, I really need to win the lottery so I can retire already and spend half the year in Italy like my ILs do.
My grandma (from my dad's side) is from Cedarchis, up in Friuli among the mountains. I don't know Milan too well but when I was little I spent many summers with my BFF (at the time) in Bergamo and Crema.
I'm sending you good lottery vibes so you can retire and enjoy Italy!