Meal with local family?

In Poland, not in Italy. We booked through Eataway.com.

Thank you for the site.

Le Cesarine is another option. Home cooks prepare a meal in their homes. From their website: “Le Cesarine is Italy’s oldest network of home cooks. They are passionate and welcoming hosts that open the doors of their own homes to curious travellers for immersive culinary experiences.” Disclaimer: I’ve not yet done this, but I keep trying to fit it into a trip. They’ve gotten quite a bit of good press over the years and I’m very curious to try.

Sorry I can't help with recommendations, but it looks like you've gotten some pointers in the right direction.

I just wanted to commend you for interest in having a meal with a local family. We had wonderful hosts at our B&B in Paris. In addition to them joining us for breakfast (at our insistence), we had a couple of dinners together. One was at their home and another time we treated them at their favorite restaurant off the beaten tourist trail. In France, our grandson had made friends with a young lady from Loches when he was attending college. Both her parents and her grandmother had us over for dinner. This is the heart of travel for us. Seeing the Eiffel Tower and Chenonceau is a great experience, but being able to break bread with others make our travels a truly memorable experience. I hope things work out for you.

I checked out Guardastelle and it looks wonderful! I see they offer tours of the winery. I recommend you take their full tour with lunch. That's what we did when we stayed at our agriturismo near Greve. Most wines are meant to be enjoyed with a meal and can't be really appreciated when tasted alone.

We've done eatwith.com in both Rome and Barcelona and thoroughly enjoyed the experience. I don't know if they have one in/near San Gimignano but I bet your lodging would know.

Great idea!