I recently returned from a 5 day stay in Urbino to visit with my daughter who is taking a summer course at the Univerity there. This was NOT enough time to explore this wonderful city. I stayed in a great hotel across the street from the Ducal Palace. (The San Domenico) It was an old convent that has been re-invented as a classy and beautiful hotel. Each day I'd walk the hilly streets while my daughter was in class. The gelato ofcourse was a wonderful way to combat the heat, and I was averaging 2 new flavors a day! At night we walked to the piazza and sat with the locals and tourists alike, drinking wine and having dinner at the outdoor cafes. We would sit on the church steps and marvel at where we were and how ancient those actual steps were. I still can't get over the old people walking the steep streets. There are a lot of young people ofcourse, and plenty of night clubs to visit.
A good day trip is to take the bus right at the bottom of the city walls to Pesaro. The buses leave Urbino about once every hour. Pesaro is a beautiful beach town on the Adriatic Coast. From there you can catch a train to almost anywhere. The people in Urbino are so nice, and helpful. We had a great time and I recommend this little gem of a town to people who like the perfect mix of tourism and local flavor.