Bologna

A 3.8 km covered arcade with 666 arches climbing Colle della Guardia to the Sanctuary of the Madonna di San Luca. Dogs on leash are welcome along the entire ascent, and the shaded porticoes make it viable even in summer heat.

Bologna's largest public park, opened in 1879 and modeled on English gardens, covers 26 hectares just outside Porta Santo Stefano. It features two fenced off-leash dog areas, a pond and shaded lawns ideal for a picnic after a long city walk.

The civic heart of the city since the 13th century, flanked by the Palazzo d'Accursio and the unfinished façade of San Petronio, one of the largest churches in the world. Dogs are welcome on the square itself, but not inside the basilica.

A dense grid of medieval lanes east of Piazza Maggiore where salumerie, cheese shops and osterie have traded since the Middle Ages. Leashed dogs are welcomed outdoors at most stalls and café terraces, though food-hygiene rules keep them out of indoor counters.

The leaning twin towers built by rival noble families around 1109-1119 are Bologna's defining skyline. The base piazza is pet-friendly, but the 498-step climb up Asinelli is off-limits to dogs and currently restricted pending restoration of Garisenda.

A 28-hectare hillside park ten minutes from the walls, with olive groves, orchards and wide views over the rooftops. Dogs may run off-leash on marked meadows, making it the locals' favorite escape for long morning walks.