Ciao Steve,
I can most definitely help you with number 1 - I know Fiamma and Ginny who are private chefs that offers meals as well as cooking classes on location wherever you might be, so since you're looking at a "hands on experience", I think you would all love to incorporate the cooking class in the afternoon and then enjoy dinner eating your creations! I did a cooking class recently with Fiamma to learn how to make homemade egg pasta and it was fun as well as a learning experience, I've since tried making it at home with my kids and we all enjoyed the finished product very much!
You can contact them directly and decide on a menu and get a quote from them so that you can block out your dates. They will drive out to your place and bring everything you need for the lesson+dinner. Here is my interview -
https://www.discovertuscany.com/tuscany-cooking-classes/interview-kitchen-chez-nous.html of them both, and I am writing another review of the cooking class which I will put up soon! I'll link to that as soon as it is online.
As far as the second request, the area around Arezzo does produce a lot of red wines in every direction, including the Valtiberina area, Casentino and Chianti (area between Arezzo and Siena) which are the closest, with the Montepulciano and Brunello wine areas are just a little further away. Problem is that what I found mostly as organized tours go is that they do not offer the transportation unless you start in Arezzo and that is for the area. Here are a few tours you can take a look at to see what is available (disclaimer, these are affiliate links):
From Arezzo, private tour for your group - up to 15 people
From Civitella val di chiana - for max 20 people --- seems to be you need your own transportation to get to nearby villa
This seems to be a private tour that will actually pick you up from your place but it isn't clear what the area is and it says up to 10 people - it might be possible to expand the size of the group, considering it is a private tour:
This is the general category for wine tasting tours from Arezzo and Cortona - includes other tours such as pecorino farm visits, wine and oil tastings, truffle hunts - lots of other options
I assume since you are in the countryside you do have your own transportation planned to move around, so some of the tours on this last link could be options if you can drive there and not rely of paying for transportation.
Let me know if you have more questions or anything else you would like to know!
