Begin with breakfast at Caffè Fiorella near Piazza del Campo — enjoy a cappuccino and a slice of crostata while watching the square come to life.
Head to the Duomo di Siena for a guided visit of the cathedral, Baptistery and Piccolomini Library; book tickets in advance to avoid queues.
Climb the Facciatone (Museo dell'Opera del Duomo terrace) for panoramic views of Siena's rooftops and the surrounding Tuscan hills.
Stroll via Banchi di Sopra to sample panforte and local pecorino at Antica Drogheria Sala, then browse nearby artisan shops for souvenirs.
Lunch at Osteria Le Logge — enjoy a seasonal Tuscan menu (try the pici pasta) in a cozy dining room just off Piazza del Campo.
Explore the Museo Civico and Torre del Mangia on Piazza del Campo; take the tower climb for sweeping views of Siena and its contrade.
Wander the narrow lanes toward Basilica of San Domenico, pausing at Pasticceria Nannini for an espresso and a slice of ricciarelli.
Visit the quieter Fontebranda area to see the medieval fountain and learn about its role in Siena's water history; great for photos away from crowds.
Aperitivo at Enoteca Italiana (Palazzo Pubblico) or a nearby wine bar on Via di Città — sample local Chianti or a Vernaccia with small plates.
Return to Piazza del Campo as the lights come on and enjoy a leisurely passeggiata; stop for photos of the illuminated Palazzo Pubblico and the shell-shaped square.
Head to La Taverna di San Giuseppe for an early dinner — savor traditional Tuscan dishes like ribollita or wild boar ragu in a cozy, stone-walled dining room.
After dinner, walk up to the panoramic terrace at Fortezza Medicea to sip a digestivo and take in nighttime views of Siena and the surrounding hills.
Stop by Bar Il Palio or Dada Cafe for an after-dinner coffee or a glass of local dessert wine while soaking up the relaxed evening atmosphere.
If you’re up for a gentle stroll, explore the quieter streets of the Contrada area, pausing at small gelaterias like Gelateria Kopakabana for a late gelato.
Conclude the evening with a nightcap at Enoteca Le Logge or a nearby wine bar, sampling a last pour of Brunello or Vernaccia before heading back to your accommodation.