San Marino ITALY

Via Urbino, as Andre' suggested, it's longer.
If you take that route, Gubbio is also along the way.

I wish there was an easy way to find and compile all the posts for a particular person on the Helpline. Every one of Roberto's posts is top quality advice presented clearly with excellent, truly helpful detail. If I could put actual stars, each of his posts would rate 5 stars. Just saying... :)

Thanks so much! You are all so helpful and the detail is so appreciated! Grazie! Judy
blogginginitaly.com

Drive through the foohills to Urbino. It is an amazing trip.

There are several places of interest on your way there from Cortona, depending on which route you choose) some might require a slight detour from the most direct itinerary. Either route is less than 3 hours (if you don't stop at all) CASENTINO VALLEY ROUTE (SS71): Cortona Arezzo Bibbiena (slight detour to Poppi, visit the Count Guidi's castle where Dante lived) Badia Prataglia (before Badia P., slight detour to Camaldoli's Monasteri and its forest) Mandrioli Pass Bagno di Romagna (enter freeway E45) Sarsina (exit freeway) San Marino (Poppi, Camaldoli, and La Verna, see below, are the stars of Casentino) VAL TIBERINA (Tiber Valley) ROUTE: Cortona Arezzo (or shortcut from Castiglion Fiorentino) Sansepolcro (enter freeway E45) Sarsina (exit freeway) then follow prior directions. If you take this route, you should definitely visit Anghiari (near Sansepolcro) and maybe Caprese Michelangelo (Michelangelo's birth house). Michelangelo was born there when his father was governor of the area sent by the Medici. If you detour, enter E45 at Pieve S.Stefano.
Anghiari is a must in the Tiber Valley. Between the Casentino Valley and the Tiber Valley you could also visit the Sanctuary of "La Verna". Very beautiful. That is where St. Francis of Assisi was during his hermitage and where he received his stigmata. Near San Marino you should visit the Malatesta Castle of Gradara, at Gradara. That is where the love story of Paolo and Francesca, in Dante's inferno is set. (Search all of the above locations online to see all locations). For Coastal locations near San Marino, I recommend Riccione. Cattolica and Gabicce Mare are also nice. They shouldn't be awfully busy yet.

I grew up on that part of Tuscany (Prov. of Arezzo). My grandparents were from there and that's where I spent a large portion of my summers (when I wasn't at the beach). Yes, I know. Italian kids don't work in Summer like American kids. They don't have as much money, they are more spoiled, but they have a good time, even with less money in their pockets. Who needs a car anyway when you can travel on a cheap Vespa. As the Vespa slogan is in Italian: "Vespa e' liberta'" (Vespa is freedom). If you really want to have a busy day, take this comprehensive route: Cortona - Arezzo - Bibbiena - Poppi - Camaldoli - La Verna - Caprese Michelangelo - Anghiari - Sansepolcro (E35 freeway) - Sarsina (exit E35) - Novafeltria - San Marino. It can be done in a full day, but it might take an overnight stay to fully appreciate everything. I can guarantee you that in a life time spent in Casentino and Val Tiberina (I have a couple of family houses in the area), I saw very few Americans there. So very little chance to meet the Rick Steves' tribes in those areas. Can't get away from the Germans though. You'll find them even in the darkest forests of the Casentino valley. PS: A little note on the Florentine steak. The Florentine steak, in order to be called such, must use meat from the Chianina breed of cows (from Chiana valley, basically Cortona), and must be grilled on a fire prepared using wood from the Casentino forests. Camaldoli is in the middle of the Casentino National Forest Park, one of the most forested areas in Italy. If it's hot, it's a nice place to go (I heard from my relatives it rained recently, that area is famous for funghi porcini. Maybe you can find some)

@Rose... could not agree more about Roberto's posts. So personal and obviously a great love for Italy @Roberto..next time you are in Italy you should set a meeting for the RS Helpline people ... I would be there! You have given me so many ideas of more obscure places to visit (which I love) :))