Day 1: The Campo and the Duomo

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.