What to see in Siena in 2 days: itinerary through contrade, Gothic art and Sienese hills
Guide to what to see in Siena in 2 days: from Piazza del Campo to the Cathedral, from secret contrade to the Sienese clays, with walking routes in the medieval centre.
Why Siena deserves 2 days
Siena has remained intact in its 14th-century layout: no Renaissance reshaped it, no building speculation altered it. The rivalry between the 17 contrade still pulses through the streets, Sienese Gothic tells an art story different from Florence, and the surrounding hills are among the world's most photographed landscapes. Two days let you experience the city's rhythm without reducing it to a postcard.
To plan your trip: where to stay in Siena, where to eat in Siena and how to get to Siena.
Day 1: The centre and the contrade
Morning — Piazza del Campo and Torre del Mangia
Start early at Piazza del Campo, when the brick shell is still empty. It is the most beautiful square in Italy — the natural slope creates a perfect amphitheatre. Climb the 400 steps of the Torre del Mangia for the complete panorama: red roofs, bell towers, Tuscan hills on the horizon.
Visit the Palazzo Pubblico: Ambrogio Lorenzetti's frescoes (Allegory of Good Government, 1338) are an absolute masterpiece — the first realistic landscape in Western painting.
Hidden gem: the Fonte Gaia in the square is a copy — Jacopo della Quercia's originals are in the little-visited Santa Maria della Scala museum complex.
Afternoon — The contrade on foot
Siena is understood through its contrade. Each district has its baptismal fountain, its museum, its colours. Walk from the Terzo di Camollia (Contrada dell'Istrice) toward the Terzo di San Martino (Contrada della Torre): you'll notice the plaques on walls, fountains with symbolic animals, painted street lamps.
Walking route: Piazza del Campo → Via di Città → Palazzo Chigi-Saracini → Piazza del Duomo → Via della Galluzza (the most characteristic) → Fontebranda → Church of San Domenico.
Evening — Via Pantaneto and Sienese dinner
Via Pantaneto is the heart of evening university life: wine bars, trattorias and bookshops. Dinner with pici with cinta senese ragù, ribollita and a Brunello or Chianti Classico.
Day 2: Sacred art and surroundings
Morning — Cathedral and Santa Maria della Scala
Siena's Cathedral is one of Italy's richest: the sgraffito marble floor (visible uncovered in August-October), the Piccolomini Library with Pinturicchio's frescoes, Nicola Pisano's pulpit. Don't miss the side door leading up to the Facciatone — the remaining wall of the never-completed expansion, with a vertiginous view over the city.
Santa Maria della Scala, opposite the Cathedral, is a former hospital turned museum: the Pilgrims' Hall with its fresco cycle on the care of the sick is extraordinary.
Afternoon — Crete senesi or San Gimignano
Two options. With a car: the crete senesi toward Asciano (30 minutes) — grey clay hills, solitary cypresses, isolated abbeys like Monte Oliveto Maggiore (cloister with frescoes by Sodoma and Signorelli). Staying in the city: the Orto de' Pecci, a medieval garden hidden in the valley below Piazza del Campo, and the Basilica of San Francesco with Lorenzetti's frescoes.
Hidden gem: the Contrada della Civetta on Via Cecco Angiolieri has a small free museum explaining contrada life better than any guidebook.
Evening — Sunset from the Medici Fortress
The Medici Fortress has a park with views of the Sienese sunset — locals come here for aperitivo with charcuterie and pecorino boards. The Enoteca Italiana inside offers tastings of all Tuscan wines.
Practical tips
- Day 1: approximately 6 km with continuous ups and downs (Siena sits on three hills)
- Day 2: approximately 4 km in the city + car for the crete
- Opa Si Pass: combined ticket for the Cathedral + all annexed museums
- The centre is ZTL: park at Il Campo or Santa Caterina (escalators to the centre)
- July-August: Palio period (2 July and 16 August) — book months in advance
