Siena 3-day itinerary

Start in Piazza del Campo, the extraordinary shell-shaped piazza that has been Siena's civic and social centre since the 1300s. The sloping brick square is ringed by medieval palaces and dominated by the Palazzo Pubblico (Town Hall) with its elegant Torre del Mangia tower rising 102 metres above. Enter the Palazzo Pubblico's Civic Museum (Museo Civico, €10) to see some of Siena's greatest art — the Allegory of Good and Bad Government frescoes by Ambrogio Lorenzetti are considered among the most important secular paintings of the medieval period, depicting the effects of wise and corrupt rule on a city and countryside that is recognisably Tuscan. Then climb the 400 steps of the Torre del Mangia (€10) for panoramic views over the medieval rooftops and the Tuscan hills rolling to the horizon.

Walk up to the Duomo di Siena, one of Italy's most spectacular cathedrals. The black and white marble exterior is dramatic enough, but the interior is overwhelming — the striped marble columns, the ornate marble floor with 56 narrative panels, Nicola Pisano's elaborate pulpit, and Donatello's bronze statue of St John the Baptist. Do not miss the Piccolomini Library, accessed through a door on the left aisle, whose walls are completely covered in brilliantly coloured Pinturicchio frescoes that look as vivid today as when they were painted in 1502. The OPA SI Pass (€15) covers the cathedral, library, baptistry, crypt, and the Facciatone viewpoint — the unfinished wall of a planned cathedral extension that offers another superb panoramic view of the city.

Spend the evening wandering Siena's contrade — the 17 historic districts that divide the city into fiercely competitive neighbourhoods. Each contrada has its own church, museum, fountain, and coat of arms, and residents are baptised into their contrada at birth, remaining loyal for life. Walk through the streets looking for ceramic plaques on building corners showing the district animal — the Tower, the Caterpillar, the Porcupine, the She-Wolf. Stop at Enoteca Italiana in the Fortezza Medicea, where you can taste dozens of Tuscan wines by the glass from €3–8. Or find a neighbourhood wine bar and order a glass of Chianti Classico (€4–6) with bruschetta al pomodoro (€3–5) and crostini with chicken liver pate (€4–6).

Visit the Pinacoteca Nazionale on Via San Pietro, Siena's principal art gallery housed in two connected Gothic palaces. The collection spans the Sienese school of painting from the 13th to 16th centuries — Duccio, Simone Martini, and the Lorenzetti brothers are represented with gold-ground panel paintings that glow with medieval intensity. Entry is €8. Then cross to Santa Maria della Scala, the vast medieval hospital complex opposite the cathedral that has been converted into a museum and cultural centre. The highlight is the Pellegrinaio (Pilgrims' Hall), covered in 15th-century frescoes showing the hospital's charitable work — feeding orphans, caring for the sick, and welcoming pilgrims on the Via Francigena. Combined entry is €9.

Walk to the Basilica of San Domenico perched dramatically on a hill overlooking the old town and the surrounding countryside. This austere Gothic church is where St Catherine of Siena — Siena's patron saint and one of only four female Doctors of the Church — worshipped, and a chapel contains her preserved head as a relic. The views from the piazza outside over the rooftops to the cathedral are among the best in the city and are free. In the afternoon, join a hands-on pasta-making class at one of Siena's cooking schools — classes run about €50–70 per person for a 2–3 hour session where you learn to make pici (Siena's thick hand-rolled pasta), ravioli, and tiramisu. You eat everything you make for lunch, paired with local wine.

Dinner in Siena should be at a proper trattoria in the back streets — pici al ragu di cinghiale (hand-rolled pasta with wild boar sauce, €10–13) is the essential Sienese dish. Start with antipasti of crostini neri (chicken liver crostini, €5–7) and a plate of local pecorino and finocchiona salami (€8–12). Pair everything with a carafe of house Chianti (€8–12 per half litre). After dinner, join the passeggiata — the Italian evening promenade where locals stroll through the streets, greet friends, and linger at cafe terraces. In Siena, the passeggiata flows along Via Banchi di Sopra and down into Piazza del Campo, which glows golden under the streetlights. End with a gelato from one of the artisan gelaterie — pistachio and ricotta-fig are Sienese favourites (€2.50–4).

Take the SITA bus (about €6 one-way, 75 minutes) or drive 45 minutes to San Gimignano, the iconic Tuscan hill town famous for its medieval towers. Once a prosperous stop on the Via Francigena pilgrimage route, the town's wealthy families competed to build the tallest tower as a show of power — 14 of the original 72 towers survive, creating a dramatic skyline visible from kilometres away across the Tuscan countryside. Walk through the Porta San Giovanni gate into the town centre, climb the Torre Grossa (the tallest tower, €9 including the civic museum) for spectacular views, and sample the town's famous Vernaccia di San Gimignano white wine (€3–5 per glass at local wine shops). The Piazza della Cisterna is particularly photogenic with its medieval well and surrounding towers.

Return via the Chianti wine country between Siena and San Gimignano — rolling hills covered in vineyards, olive groves, and cypress-lined roads that define the Tuscan landscape postcard. If you have a rental car, stop at a roadside cantina for a wine tasting — many estates offer tastings with 3–4 wines plus olive oil and bruschetta for €15–25 per person, no reservation needed. Chianti Classico, the premium designation from the zone between Siena and Florence, is rich, earthy, and perfect with the local food. Even without a car, several Siena-based tour operators run afternoon Chianti wine tours from about €45 per person including transport and tastings at 2–3 estates. The landscape alone is worth the trip — golden light on green hills, medieval farmhouses, and rows of vines stretching to the horizon.

Return to Siena for a final evening in Piazza del Campo. Buy a bottle of Chianti (€6–10 from an alimentari shop), some pecorino cheese, and a baguette, and join the locals and travellers sitting on the sloping bricks of the piazza as the last sunlight warms the brick facades of the surrounding palaces. The piazza transforms as the sun sets — the Palazzo Pubblico glows gold, shadows lengthen across the shell-shaped square, and the Torre del Mangia stands silhouetted against the deepening sky. This simple ritual of sitting in one of the world's great squares with good wine and the company of fellow travellers is Siena at its most perfect. For a final dinner, try ricciarelli (soft almond biscuits, €3–5) and vin santo (sweet dessert wine, €4–6 per glass) at a nearby cafe.