We will be staying near Cortona for one week in mid-May and will have a rental car for transportation. We would appreciate recommendations for 4 or 5 excellent excursions/day trips that are "must do" for our first time to Italy. We will already have been to Rome, Florence, Volterra, and Lucca before arrival at Cortona.
I love Gubbio - maybe an hour's drive or so from Cortona? Lovely lovely old historic town, a really wonderful open-air-cage "funicular" in which you ride standing up to the top of high hill above the town, and can then relax at an outdoor cafe looking waaaaayyy out over the valley. Oh, and there's some pretty great shopping for handpainted ceramics, if that's your thing, too! We found very easy parking some three blocks from the elevators (yes!) to the high, older part of town.
Also: We daytripped to Gubbio from Assisi so - the obvious - Assisi is no doubt within a couple of hours' drive from Cortona.
When we stayed in Cortona last time, we drove to Asissi, Perugia, and Spello. Another day we took in Montepulciano, Pienza, and San Quirico. You are close enough to visit Greve and Panzano too.
Each direction was completely different ! The Chianti region has winding roads and vineyards galore. The Montepulciano region has endless fields of poppies. All of the villages are fun in their own right - we stop at each and have a cappuccino and pastry.
Orvieto's about 75 minutes a way and great. Try for a weekday if possible, since it seems to get some extra weekend visitors. Check hours of cathedral and museum for closing days/times.
Siena's even closer.
Todi! Just a wonderful hill town with walls, gardens, views over the valley. Not convenient by public transportation, so fewer tourists.
Also Montefalco and Trevi.
JBW,
You may enjoy reading Frances Mayes book, 'Every Day in Tuscany', in which she writes about her life in Cortona, and traveling to nearby towns and cities such as; Foiano, Castiglion Fiorentino, Arezzo, Sansepolcro, Città di Castello, Umbertide, Perugia, and Orvieto, to name a few.
You may also consider visiting Castiglione del Lago, Siena, Assisi and Todi.
If you like ceramics, check Deruta, just South of Perugia.
Have a wonderful trip!