restaurants in umbria
I spent part of 2 summers in cortona about 8 years ago. Not sure if this info is reliable anymore, but in Italy restaurants don't change as frequently as they do here, so. There's a pizza place just outside of Cortona up on the hill. My family referred to it as "Pizza on the hill" Go through town and about 2 or 3 kilometers it's on the right looking over the hill. Very family. Terrific individual pizzas (my introduction to quattro stagione), thin, slightly charred crust, a slip of tomatoes, each quadrant draped in a "season": ham, mushrooms, artichoke and olives?. Wonderful and cheap house red wine. Lots of families.
In the town of Cortona there's Il Grotto, at the end of town, just before the church which serves the best ricotta gnocci with sage and butter sauce. It's incredibly delcious and they only serve it at lunch, which is a plus, because they have outdoor tables at lunch too.
Then there's a place called the Locanda di Scourci-- I'm not sure where it is (about a 45 minute drive) maybe near Montepulcro? -- which serves this incredible sunday lunch. Large semi-communal tables, lots of mulit-generational families and a parade of family-style delicious food so intense you may not get through the meat course. Warning: pace yourself. The Antipasti and 2 pasta courses always slayed me. By the time the platter of assorted grilled meats (marinated w/ olive oil and rosemary) and vegetables came I always had to eat really fast because i would have no appetite by that time; but ate just becuase it's there, because it's amazingly irresistable; and because 8 years later i can still taste-imagine the most perfect papardelle with sugo and tuscan roast chicken.
It's always been my experience that Italian restaurants generally have no problem with the bambini. They go out of their way (even at semi-fancy places) to placate the kids. They're a lot less up tight than NY restaurants. In fact I have a memory of being in Italy w/ my parents when I was five and was taken to the garden by the host to see the giant turtle living out there. And given an extra bowl of raspberries. A formative dining experience, indeed.
Have a great time. I'm jealous.
In general, Umbrian cooking of lesser interest than Tuscan. While the pastas and soups are delightful, such as those served the excellent Castello dei Sorci mentioned by Jen Kalb, the secondi piatti (main courses) tend to be dull, usually highly-salted grilled meats. Cortona used to be incredible: one trattoria owner drove up to Genoa to buy his basil for pesto. Stick to the small towns and if older cooks are present, you will do well. Also, Spello has good trattorie (out east near Foligno).
First off, I recommend that you consult, if you havent already, Faith Willingers book with many many recommendations for wonderful eating in the Umbria/Tuscany regions and northern Italy generally.
Re: family suitable restaurants I have some suggestions in Tuscany from my own experience there with my kids a while ago. Outdoor seating where the kids can wander off a bit when they finish, long before you do, is best. this suggests a very small town or a country restaurant, not a bustling city center. Some places I remember with a garden/outdoor eating area or other suitable space are: (1) the restaurant (la Torre) at Monte Oliveto Maggiore - acceptable food served on a terrace behind a castle - with a drawbridge and moat, as I recall, a short walk from the monastery and its amazing Signorelli frescos. As a bonus, this place is in the "crete" - that improbably landscape SE of siena immortalized in all those sienese paintings. (2) Pulcino, just southeast of Montepulciano, with their own wines and olive oil. A huge country restaurant with long communal tables, and plenty of room for kids. Montepulciano is a pleasant hill town good for a morning's stroll, not extraordinary, but the San Biago church just outside the town is glorious. (3) Castello di Sorci,nr Anghiari or Monterbone (e of Arezzo, if you are looking at Pieros its a great stop) A country restaurant right smack in the middle of a big green field, with excellent value for a fixed price homestyle meal - the setting is great. (4) Umbra in Todi has been recommended to me (tho I dont know about the kid part, it is a very small town) (5) I have happy recollections of eating at the outdoor seating area of the Castello di Gargonza restaurant, which lies west of Monte San Savino on the Siena road, when we were staying there 15 yrs ago. Roasted dishes, wild boar, spinach canneloni etc. served with the gargonza estate's wines and oil. Its in the middle of the country and your kids can play at the little playground right there or run up the hill to visit the restored castle village. (6) there may be some places to visit on the Lake Trasimeno island - a good summer destination for informal meals. Finally, in Umbria, we greatly enjoyed Taverna del Lupo in gubbio, which was relatively informal - it may have been gussied up since that time - Gubbio restaurant in NY is some kind of NY progeny. Gubbio is also an exceedingly attractive town.
Hope you have a lovely trip, and report back on your finds.