Hi bubblywine, I am delighted that you read my post and further more than you agree. So when in Cortona keep climbing up , it is an easy walk, the tangle of Cortona's old stone streets and alleys and you will find your selves in the Baslica of Santa Margherita , a Saint with an amazing life.
I must confess I am also delighted to see that you are planning with care and love your trip with your Grandmother, cherish it, it will remain forever in your heart.
I have seven grandchildren and two years back I took our oldest grandson Jeronimo to Rome and Firenze and we had a ball, same way I cherrish each and every trip with my grandmother that happened long ago.
Frankly when we read about real bad things like lately in Connecticut and things like that we need to be reassured with hope, and good things. So I hope the best to your Grandmother and to you
and over there pray for this country and actually for the whole world it seems it is needed. Ciao.

In reply to visits to vineyards I recall the monks working in vineyards in The Celle, the Franciscan hermitage just five kilometers from Cortona at the feet of Mount San't Egidio, but even if the vineyards are not a great deal, it worth a visit. We also had a good lunch at Il Falconiere, not far from town it does overlook a valley sprinkled with vineyards and orchards.
Speaking of churches the Madonna del Calcinaio is a gem of the Renaissance it is located on the outskirts of town, I recall it is not easy to find it open.

...one more thing, I recall it was an easy walk to Santa Margherita's but just in case, do not take my word, check with the hotel...

As you visualize all that wine tasting, keep in mind that the qualification for drunk driving under Italian law is at a significantly lower blood alcohol level than the laws where you're from. Also, if you're not aware, you'll need an International Driving Permit.

You're wonderful, Graziella! My Grandmother took me on a number of trips when I was in my teens and they were so well planned. It is nice to be able to repay her in this way and I feel like the luckiest of all her grandkids for the opportunity.

Thanks for the tip about lunch at Il Falconiere. It looks spectacular, but I wasn't finding info about lunch - might add that into the eating plan (which is rather large).

Mass at the Basilica is really special. I highly recommend it. Also, since your are Catholic (I assume) the town is also home to Saint Margaret of Cortona and I think her body is there somewhere. I can do some more checking if you wish.