History & Tradition · ~35 min from Chianti
If Florence evokes the Renaissance, Siena evokes the Middle Ages. This city has remained true to itself through the centuries, preserving a remarkably complete UNESCO-listed historic centre. Step through its medieval gates and the pace changes: reddish brick that gives sienna pigment its name, neighbourhood flags and unexpectedly quiet lanes.
One of Europe's most beautiful squares, its shell shape draws the streets and their rainwater towards the centre. Palazzo Pubblico and Torre del Mangia stand proudly along its edge. Sitting on a travertine step with a coffee, watching sunlight cut across the shadows of medieval buildings, is a moment to remember. Climb Torre del Mangia (503 steps) for a view stretching across the Val d'Arbia.
Siena Cathedral is a masterpiece of Italian Gothic architecture. Its black-and-white façade leads to an interior striped with white and green marble. The Piccolomini Library houses Pinturicchio's brilliantly coloured frescoes. Another treasure lies underfoot: 56 marble inlay panels telling sacred stories, fully uncovered only during the summer months.
💡 The Palio of Siena
The Palio takes place on 2 July and 16 August. If you are staying in Chianti then, it is a unique experience. Arrive in Piazza del Campo at least four hours early to find a standing place in the centre. Paid grandstand seats need to be booked months ahead.
Siena is divided into 17 contrade, historic neighbourhoods with their own identity, symbol, colours, church and museum. The Palio is the best-known expression of their centuries-old rivalry. But the contrade are active all year, with communal dinners, neighbourhood celebrations and rituals handed down through generations.
Sienese cooking is generous and rooted in tradition. Pici, thick hand-rolled pasta served with a meat sauce or aglione garlic sauce, is a local favourite. Almond ricciarelli and panforte are the city's signature sweets and make lovely gifts to take home.
"Siena quietly finds its way into your heart. Before you know it, you are longing to return."
Siena's historic centre is pedestrianised. Park outside the walls; Il Campo and Santa Caterina are convenient options, then explore on foot. Allow half a day for the main sights or a full day to wander the lanes at leisure.