Trattoria da Piero e Silvana
This is a simple restaurant with a great representation of umbrian cooking. It's cozy and the people are friendly.
Gelateria Pianegiani
I love the gelato here. They have a nice little square with tables and chairs to sit. It's just down the street from Pizzeria Cavour or up the street from Trattoria da Piero e Silvana. If you want to take some home, they have various sizes of styrofoam containers that they will fill with a variety of flavors for you. ...although you better be heading straight to the car and home from there.
La Torraccia
A casual cocktail bar and pizza place with lovely views is walkable and located at the entrance gate of Monte Castello. There is a little staircase to the left as you face the arch. It is located along the exterior wall of the town. It is only open in the summer and it operates a bit like an italian beach club with various aperitivi (cocktails) and casual food. The pizzas are pretty good. Sometimes, we just stop by for a drink in the evening after we have picked up something to grill from the butcher in town. They advertise bands and dancing but I've never stayed long enough to check it out.
Hosteria Mattta
This is a small restaurant run by a crazy but passionate lady. She speaks English. There is a small outdoor patio in the back that is fun to sit on if you have a small (under 6) group. She changes her menu every few weeks and loves to converse with her guests and make recommendations. The food was very good and creative. We ate here for two lunches. It's open for lunch and dinner and closed on Tuesdays. This restaurant can accommodate any type of food restrictions and is particularly good at gluten free. You could park in the city lot for free and walk up into town or there are a small number of parking spaces just past the restaurant. Marsciano is a 15 minute drive from the house. …
Osteria Novecento
Osteria Novecento is by far the best restaurant in the area. I would go here at the beginning of your trip because you will likely want to visit it a second time before you go. The restaurant features typical umbrian fare but with a gourmet delivery. We've never had anything bad here and have tasted most things on the menu. They also have specials that change regularly. It is a small restaurant so you will definitely want reservations if you are a large group or if it is a weekend. The waitress speaks some English. It has a couple of outdoor tables but no real view. It is cozy in the winter with an indoor fireplace. From Casa Grifone it's about a 20-minute drive. You go across the highway exit opposite…
Pizzeria Cavour – Todi
For unique and delicious pizzas and a beautiful outdoor view in Todi, go to Pizzeria Cavour. We've been coming to this place since the very first time we visited Umbria in 2003. It's likely considered by locals to be more touristy but I still love it. Ask for a table outside (a fuori). Enjoy pizzas like pear and gorgonzola or one with squash and truffle or any of the basics if you aren't into unusual flavors. They have an English menu and most of the staff speak English. The main waiter is pretty cranky - that's the only downside - so get your order in at the beginning because he won't likely come back to check on you later (i.e., order plenty of drinks when you place your order.) Although…