Meet up with your local guide at the Basilica of San Domenico, the gorgeous Gothic church made of red brick. Set off with your guide walking the narrow cobblestoned lanes, learning about the various contrade, or neighborhoods, all of which have a distinct personality and character. Stop at Palazzo Tolomei, the oldest private palace in town.
Then head over to Piazza del Campo, the seashell-shaped space that has been the public living room of locals for centuries. Admire the Fonte Gaia, Fountain of the World, built in 1419; look up at at the tall campanile, attached to the 14th-century Palazzo Pubblico.
After some time, move on from the square and head to the Siena Duomo, one of the most awe-inspiring cathedrals in Europe. Take in the black-and-white-striped facade and then breeze right in to the interior thanks to your skip-the-line ticket. Inside, let your guide lead you around, revealing priceless works of art by Donatello, Bernini and Michelangelo. Take in the Gothic interior of the cathedral, along with Renaissance-era busts of pope and emperors.
When the tour is over, you'll feel connected to Siena like never before.