I spent a couple of day in Urbino. It is a nice medieval town. Nowadays it is a university city and, during school days, there are more student than hinabit so you can find not expensive shops and restaurants. I stayed in the La Brombolona hotel, it was in the countryside a few km away from the town and I found it wonderful (you must have a car to go there). You can find contact details in the Hotel database.

About day trips, yes, Urbino could be a good choice as a base. Take day trips to the medieval town of Gubbio and Citta' di Castello, to the wonderful town of Perugia and Assisi in Umbria region. Don't miss San Leo (close to San Marino), there is a wonderful castle at the top of an hill (nice view!), visit the state of San Marino and the town of Gradara (close Cattolica along the highway) where there is a nice medieval town and castle. Not far from Urbino you can visit the Monastero di Fonte Avellana, a monastry in the Marche countryside.

For quite long one day trip, you can get to Loreto Abbey (South of Ancona), to Ravenna well known for its wonderful mosaics and churches.

Definitily I think it is a good idea take base in Urbino ... if you have your own car.

Enjoy, Marco in Milan - Italy.