Siena

The shell-shaped square at the heart of Siena, split into nine brick segments converging on the Palazzo Pubblico and the Torre del Mangia, one of the finest medieval squares in the world. Always open and perfect on a leash; the palace interior and the tower climb are closed to dogs.

A 16th-century brick fortress built by the Medici, whose broad flat ramparts now form a panoramic promenade much loved by Sienese and their dogs. Free on a leash at any hour, with views over the Crete Senesi hills; the adjoining Lizza gardens are shaded for a break.

A medieval green valley just below the Piazza del Campo, with vegetable plots, vines, farm animals and broad lawns, a pocket of countryside in the very centre. Leashed dogs welcome on the paths and lawn, with a café-restaurant terrace that accepts dogs, ideal for a breather away from the lanes.

A Gothic cathedral banded in black-and-white marble, one of the most spectacular in Italy, crowning the city from its highest point. The forecourt and surrounding lanes are free on a leash to admire the façade; the interior, crypt and Piccolomini library are reserved for assistance dogs.

The ancient Canterbury-to-Rome pilgrim route runs through Siena via Porta Camollia in the north and Porta Romana in the south, marked by medieval gateways. The stretches leaving the gates, through olive groves and hills, make excellent leashed walks away from the centre's crowds.

The clay hills southeast of Siena, the emblematic Tuscan landscape of rolling ridges, cypresses and lone farmhouses. A 20–30 minute drive or Tiemme bus away, with trails and white gravel roads perfect for long leashed walks; no shade, so set off early in summer.