Walking Siena’s Medieval City Walls: A Self-Guided Route

Siena’s medieval walls are not a single continuous structure like Lucca’s, but a fragmented network of gates, towers, and ramparts that encircle the old city. Walking them gives you a perspective most tourists miss — the backside of cathedrals, the gardens of contrade, and panoramic views over the countryside. This self-guided route takes 90 minutes and requires no ticket.

The Route

Start: Porta Romana (southwest gate) Begin at the largest surviving city gate, built in the 14th century. The brick arch still bears the Medici coat of arms from the siege of 1554. Walk east along Viale Vittorio Emanuele II.

Stop 1: Bastione di San Paolo A partially collapsed bastion with a viewpoint over the Chianti hills. In spring, the meadow below is carpeted with wildflowers. This is a favorite picnic spot for university students.

Stop 2: Porta Tufi The eastern gate opens onto an olive grove path. The 13th-century tower is intact, and the stone lion carving above the archway is one of the oldest in Siena. Walk through the gate to see the countryside path; you do not need to leave the route.

Stop 3: Fortezza Medicea The star-shaped fortress dominates the northeast corner. Walk the outer walls for views of the Duomo’s apse — a view you cannot get from inside the city. The ramparts are free to access.

Stop 4: Porta Camollia The northern gate is the most ornate, with a Baroque arch added in the 1600s. The inscription above the gate reads "Cor magis tua Sena pandit" — Siena opens its heart wider than its gates.

Stop 5: The Back of the Duomo From the walls near Porta San Marco, you see the cathedral’s Gothic flying buttresses and the unfinished nave extension that would have made it the largest church in Italy had the plague not bankrupted the city in 1348.

End: Porta Romana Close the loop. Total distance: approximately 4 kilometers.

What to Bring

• Water. There are fountains at Porta Tufi and the Fortezza.
• Comfortable shoes. You will walk on grass, gravel, and cobblestones.
• A camera. The light on the terracotta rooftops at late afternoon is extraordinary.

Where to Eat Along the Way

The route passes close to Viale Sardegna, where La Napoletana 2.0 serves wood-fired Neapolitan pizza. It is a 10-minute detour from Porta Romana. The mortadella and pistachio pesto pizza is a fitting reward after a long walk.

Best time: Late afternoon, two hours before sunset. The western-facing ramparts catch the golden light, and the temperature drops as the sun sinks behind the Crete Senesi.