I'm sure the guy in the first photo is Alan who runs Across the Tracks in Sydney street, he is the one to right with black shirt and his hand on his chin. I'll show him when i see him next.
Me and the wife had a week in Florence in 2022 also a week in San Gimignano and visited Lucca. Beautiful places but very expensive especially San Gimignano it is very difficult to find a dinner table as the large American tourist groups have them booked in advance !