Cortona wine tour

I'm not big on organized tours, but because you named a town, I'll mention another option you might have - maybe even if you have to use a taxi. We had the best meal of our stay, and the best tasting of our visit, at Aviognesi Winery's lunch restaurant, not that far from Cortona. It took four hours, maybe, for the field and winery tour, the tasting, and the open-air (but covered pavillion) magnificent, gourmet lunch with wine pairings included. They even welcome you upon arrival with someone else's (because they don't make sparkling wine) prosecco. Superb experience, and interesting winemaking decisions, with property in more than just Tuscany.