Pesaro
Geographically, the town of Pesaro [in the Marche region of Italy on the Adriatic coast] is practically perfect. Its beachfront locale adds to the beauty of its winding, ancient pedestrian zone (flat, even!) and backdrop of undulating hills. The historic centre deserves an entire day to wander. The composer Gioachino Rossini loved his home town so much he willed Pesaro all of his possessions when he died (be sure to check out Casa Rossini while you’re here).
Nearest airports: Rimini [40kms] & Ancona [80 kms].
Pesaro is on the Bologna–Lecce train line and you can reach Rome in four hours by changing trains at Falconara Marittima, just before Ancona. There are hourly services to Ancona [45 minutes], Rimini [40 minutes] and Bologna [two hours].