My wife and I plan a trip to Italy in May. We will rent a car and small apartment outside Assisi for two weeks. We assume this will be near by, yet less hectic than Tuscany. We are unfamiliar with Italian wines and would appreciate suggestion for places to eat and sample wines. Sagrantino in Montefalco is one suggestion.
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Our info is from 2004, so it's a little dated:

Montelfalco: we did not find any fine dining. We ate at Ringhiera Umbria in town. Quaint place for pizza and the owner is talkative.

Spoletto: great lunch at Il Tartufo. We killed a bottle of wine and sat there for about 2 hours. My memory is that there were only about 6 people there for lunch. Recommend.

You may enjoy going to Gubbio, a hill town. We ate at Taverna del Lupo as it was recommended to us, but I do not recommend it. It was a tourist trap with overpriced food and wine.

Trevi is quaint for a short visit and walk.

Torgiano has the wine and olive oil museum there.

Southern Tuscany. Don't limit yourself to Umbria. It's not that bad a drive in the south. (In fact, I never had a problem driving in Tuscany).

Montalcino - Go to the Castle. My memory is that Jcocktosten was there too and there is a wine bar. You can also drive out of town and drop in and visit Banfi without an appointment. I believe that they have a decent restaurant there too. You may need reservations.

Montepulciano: lunch or dinner at Le Logge di Vignola. One of the best meals of our trip (also expensive). Highly recommend.
There are lots of threads on this - Futronic, Longboarder, Otis et al. have more recent infro on Montalcino dining as apparently our favorite place has gone downhill -

The Fortezza is interesting - all our tasting was comped so that certainly helped - I would make some appointments at montalcino wineries if I were you.

Pienza is a pretty town - certainly worth visting also -

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