Hi all,

Looking for winery and restaurant recommendations for our anniversary trip mid August (I know is the most crowded time to be in Europe/Italy but we had to travel this week). We are driving from Florence to stay at Castello di Castle and then to Castiglion del Bosco. Three nights in each area. It has been awhile since we went to Tuscany so looking for must-see NON touristy winery recommendations. Also open to any stand out restaurants as well which I know there are a lot. Any near those locations? Some recommendations we heard already were Colle Bereto, Castello di Ama and Badia a Passignano if anyone has experience with those. We went to Poggio Antico in the past for context and really enjoyed it. Thanks all as always!!

I have been to Castello di Ama and loved it. It was recommended by an Italian friend who is a sommelier. The owners are also art enthusiasts so there are interesting art installations all over the property. The tour was really good, the wine is delicous and they have a very good restaurant where I had a delicious lunch.

I can recommend Fattoria Tregole, small, mother-daughter winery near Castellina in Chianti. We had a wonderful lunch and tour there several years ago. https://www.tregole.com/index.php/en/

"must-see NON touristy winery recommendations."
oh boy.

Ha. What I meant by must-see non touristy is, we would appreciate anything less mass market, could that be smaller or more picturesque is always nice.

Castello di Ama fits that bill.

I'd check to see if winters you want to visit are open in August for visitors.
The workers will be there but maybe the higher-ups will take vacation in August, like half the population of Italy.