Siena Private Walking Tour: Traditions, Streets & Cathedral

On a guided walking tour, discover Siena, its famous monuments, and hidden treasures. Enjoy skip-the-line tickets to head in faster and start exploring more quickly. Catch quiet moments in tucked-away squares and cobbled streets as you explore the medieval neighborhoods. Enhance your experience with an extended visit to the Cathedral Complex, Crypt, and Museum.

Meet your expert guide to walk the streets of Siena. Start exploring the medieval history of Siena and then walk the winding path that offers a beautiful of the Duomo and Torre del Mangia from afar. Stop here for a hot second for a lingering first glance of Siena!

Discover how this seashell-shaped square (a UNESCO World Heritage Site and one of the most squares beautiful in Italy) was the result of an enlightened 14th century government. Siena is a city with deeply-rooted traditions, none more notable than its Palio horse race which for centuries has divided the city into neighborhoods known as "contrade." Learn about the contrade, which become like independent towns that challenge each other twice a year during the Palio! Walk through one of the most typical contrada and be immersed in the authenticity of the atmosphere in Siena. The city's past was glorious, particularly during the Middle Ages, and your guide will explain how even the local pastry reflects its prosperity during that era. Ask your guide where to find the best local bakery that still uses centuries-old recipes to make typical Ricciarelli or Panforte.

See the magnificent Fonte Gaia fountain which adorns the higher part of Piazza del Campo. Take a break as to admire the sides of the piazza which are decorated with reliefs representing The Creation of Adam and The Flight from the Garden of Eden.

Admire the striking tower standing tall in the middle of Piazza del Campo. Listen as your guide explains the medieval politics of Siena which explain why its tower was built at the same height as the cathedral.

Our pre-booked tickets make entering the stunning Cathedral a breeze, and our small groups or private tours offer each of our guests a more personalized, intimate experience. Skip the line to enter the cathedral with pre-booked tickets. Inside, you'll see the magnificent marble mosaic inlay floor and astonishing decorations by famous Tuscan artists. Discover the medieval masterpieces by Duccio and Pisano, and the cathedral's renowned stained glass. Inside are several other unmissable Renaissance highlights: Donatello, Michelangelo, and Bernini sculptures, and frescoes by Pinturicchio in the Libreria Piccolomini. Here is where Raphael, then a novice painter, took his first steps towards eternal fame.

Enhance your experience with the extended tour if you want a more profound knowledge of the cathedral’s complex. After a tour inside the Duomo with your knowledgeable guide, continue your adventure at the enchanting Crypt, a true medieval gem. Marvel at the frescoes illustrating biblical episodes that had remained hidden for five hundred years, making the Crypt an authentic time capsule. Admire the vibrant colors, the level of detail, and the beauty of mural paintings. Once outside, you’ll discover the intriguing tale of the unfinished Duomo Nuovo, a visionary project intended to build the largest medieval cathedral in Europe. Visit the Museo dell’Opera and marvel at the original cathedral sculptures by Donatello and Giovanni Pisano, as well as the original stained glass window by Duccio di Buonisegna.