Italy was not designed for strollers. Cobblestones, stairs, narrow sidewalks, and medieval streets are the norm. But some cities are better than others.
Plan your trip →Best: Milan (flat, modern sidewalks, metro has elevators), Bologna (flat, porticoes provide shelter), Turin (flat, grid layout). OK: Rome (mostly flat but cobblestones everywhere — use pneumatic-tire strollers, not plastic wheels), Florence (small center, some pedestrian streets), Naples (flat seafront, but old town is chaos). Worst: Venice (440 bridges, no wheels of any kind), hill towns (San Gimignano, Orvieto, Assisi — stairs everywhere), Cinque Terre (vertical villages, stairs + cliffs). Amalfi Coast: terrible for strollers (steps, narrow paths, bus access only). Use a baby carrier.
Bring a lightweight, narrow stroller or a baby carrier (marsupio). Italian stores sell Chicco/Inglesina strollers if yours breaks. For Venice: baby carrier is mandatory. For hill towns: carrier or leave the stroller at the hotel. Public transport: buses have designated spaces. Metro: elevators exist at most modern stations (check ahead for older stations).