Sounds like a great tour.
we did a private tour with Rome in Limo, they are really more drivers than two or guides, but we have always had excellent commentary. The company will make a tour for you, or you can research and find the spots you want to go on your own. I arranged for a private lunch in the vineyards at Tenuta Torciano and it was the most wonderful travel experiences we've ever had. We ate under a beautiful pergola in the middle of the vineyards, and delicious food, and as you said, had nine glasses, sitting in front of us, and had nine tastings. It was so memorable, I hope you can go there.