Ultimate 3-Day Siena Itinerary: Best Things to Do & See

Start your Siena adventure at the iconic Piazza del Campo, the city’s stunning shell-shaped main square, famed for its medieval architecture and the legendary Palio horse race.

Piazza del Campo

Enjoy a classic Italian breakfast at Bar Il Palio, overlooking the Campo, for a cappuccino and fresh pastry in a vibrant setting.

Bar Il Palio

Explore the breathtaking Duomo di Siena, a masterpiece of Gothic architecture with intricate striped marble, vibrant frescoes, and the remarkable Piccolomini Library.

Duomo di Siena

Climb the Facciatone for panoramic views of Siena’s rooftops and Tuscan hills—an unforgettable sight for photographers and dreamers alike.

Facciatone

Dine at the atmospheric Osteria Le Logge, a local favorite for creative Tuscan cuisine in an elegant, historic setting just steps from the Campo.

Osteria Le Logge

Discover masterpieces of Sienese painting at the Pinacoteca Nazionale, home to works by Duccio, Lorenzetti, and Simone Martini in a grand 15th-century palace.

Pinacoteca Nazionale

Stroll through the labyrinthine Contrada della Torre, one of Siena’s historic neighborhoods, to spot symbols, fountains, and the authentic spirit behind the Palio.

Contrada della Torre

Lunch at Trattoria La Tellina, a cozy spot beloved for hand-rolled pici pasta and hearty, home-style Tuscan recipes.

Trattoria La Tellina

Visit the stunning Basilica di San Domenico, an imposing church housing the sacred relics of St. Catherine of Siena and famous for its peaceful, cavernous interior.

Basilica di San Domenico

For dinner, indulge in local wines and rustic specialties at Enoteca I Terzi, an atmospheric wine bar tucked into Siena’s medieval streets.

Enoteca I Terzi

Step back in time at Palazzo Pubblico, Siena’s grand town hall, and admire the civic frescoes of Ambrogio Lorenzetti and Simone Martini.

Palazzo Pubblico

Climb the slender Torre del Mangia for an exhilarating bird’s-eye view over Siena’s rooftops and countryside—worth every step!

Torre del Mangia

Pause for lunch at Antica Osteria da Divo, where you can dine in atmospheric Etruscan caves and savor truffle dishes and Tuscan classics.

Antica Osteria da Divo

Unwind in the green oasis of Orto de' Pecci, a charming urban garden with walking trails, farm animals, and views back toward Siena’s skyline.

Orto de' Pecci

End your Siena journey with aperitivo at Liberamente Osteria, where you can sip local wines with a view of the illuminated Piazza del Campo.

Liberamente Osteria