Morning: Your journey begins in Piazza del Campo, unique for its shell shape and the setting for the famous Palio horse race. Admire the Palazzo Pubblico and, if you're up for it, climb the 400 steps of the Torre del Mangia for an unparalleled view of the Sienese hills.
Lunch: Wander the alleys around the square and stop at an osteria for a plate of Pici (thick handmade spaghetti) with wild boar ragù or "cacio e pepe."
Afternoon: Visit Siena Cathedral: it's more than just a church, but a treasure trove with a marble floor that's a unique work of art. Also visit the Piccolomini Library to admire the frescoes, still in vibrant colors.

Morning: Explore the Santa Maria della Scala complex, a former pilgrim hospital transformed into an extraordinary museum. Then wander aimlessly through the alleys, looking for the fountains and flags marking the boundaries of the Contrade (the city's districts), to understand Siena's true social soul.
Lunch: Enjoy a platter of Tuscan cured meats (finocchiona, prosciutto) and Pienza pecorino cheese, accompanied by a glass of Chianti Classico.
Afternoon: Visit the Pinacoteca Nazionale to see masterpieces of Sienese painting (gold-ground paintings). Conclude with a stop at a historic pastry shop to sample Panforte or Ricciarelli, the city's typical spiced sweets.

Morning: Head to the imposing and austere Basilica of San Domenico, which houses the head-relic of Saint Catherine. From here, you can enjoy one of the most photographed views of the Duomo, towering above the rooftops.
Lunch: Try ribollita (bread and vegetable soup) or Sienese tripe at a traditional trattoria in the Camollia district.
Afternoon: Stroll to the Fortezza Medicea. Its ramparts are now a public park, perfect for relaxing. End your journey at the Enoteca Italiana (often located in the fortress or downtown) for a final tasting of the great local red wines.