Private Walking Tours in Siena, including the Cathedral, Palio, Duccio di Buoninsegna and artisan shops


Private Tours in Siena


The Cathedral, Il Campo, Artists & Artisans
Visit a Contrada Headquarters and Learn about the Palio


The Cathedral, Il Campo, Artists & Artisans

Let our experienced, entertaining and erudite private guides lead you back into the Middle Ages in one of Italy's most pristine historic cities, beautiful Siena. We know for sure that it was a Roman colony, but its origins probably go back to the Etruscans, who were vanquished by the Roman legions. Perhaps it was this early "bad blood" that made Siena a notoriously disrespectful colony; even today the Sienese continue to be fierce rivals of nearby Florence, with their own way of life, their own beliefs and their own traditions. As you visit the winding streets and alleys, paved with their original cobbles and lined with centuries-old palazzi, your guide will regale you with tales about the wars between the two great Tuscan cities -- you will learn why that animosity began, how it turned into all-out warfare, and why the battle has never been won by either side (although each side says THEY won!). As you stroll, you'll see hardly a sign of the 21st century because this city has stubbornly protected its historic appearance, making it a gem few travelers want to miss. You will visit the spectacular cathedral, one of the leading examples of the Italian Romanesque-Gothic style. It took 200 years to build -- you'll understand why once you see the exquisite striped-marble façade, as well as the breathtaking interior with its soaring golden cupola supported by massive marble pillars, and gigantic nave adorned with glorious frescoes. Artistic masterpieces abound all along the route of your walk, which will also include stops at the shops of local artisans, who practice trades handed down by generations of ancestors. The day culminates at Piazza Il Campo, the unique oval-shaped town square where the world-famous Palio horse race takes place twice a year. The stories of Siena reach their climax as your guide explains about the 17 contrade (neighborhoods) whose rivalry has existed since the 7th century. Afterwards you will step inside the imposing Palazzo Vecchio and visit its museum, a treasure-trove of early Renaissance art.

2016 All-inclusive price:
1-2 People: 206 EURO/group
3-6 People: 216 EURO/group
7-8 People: 231 EURO/group


This private walking tour lasts three hours from the time you meet your guide in front of a centrally located hotel in Siena. Meals and transportation are not included in the price. Entrance tickets to the Cathedral and the Museum cost 16.50 Euro/person extra, paid directly to the guide in Euros cash. If your group includes at least two adults plus children, up to two of the children under 18 years old pay nothing for the tour except for entrance tickets. If you have more than two children, all the others pay the adult price for the tour no matter their age.
Line Break


Visit a Contrada Headquarters and Learn about the Palio

Siena is magic; it's the quintessential medieval jewel representing everything we imagine when we think of Tuscany: history, art, architecture, food, wine, and most of all, pageantry! Even in a country like Italy, where every single town and city has its ageold traditions, none are more famous than Siena's Palio, which takes place every July 2 and August 16. The event is known around the globe as a totally unique horse race, but it is much, much more. Preparations go on all year long in Siena, whose 17 neighborhoods invest every spare Euro and every waking moment in their efforts to win. The evening before the race it is estimated that 25,000 people eat outside, as each contrada (neighborhood) stages a sumptuous banquet to "rehearse" their surefire victory celebration. To some outsiders this may all seem like much ado about nothing, but when you realize that these contrade have been virtual minirepublics for centuries, where every single member has a role with no sexual or social discrimination, and frenzied preparations go on all year round, it becomes clear why no visit to Siena would be complete without a visit to a contrada, and there could be no better way to do that than this brand new opportunity we offer you.


Spend a few hours with our old friend Dario Castagno, bestselling author, esteemed tour guide and dedicated Tuscan farmer. You'll visit the headquarters of his beloved Nobil Contrada del Bruco (Caterpillar) where, as he says, "I have the pleasure to open the private rooms of the società and show you the medieval costumes we wear on special occasions, the Palio banners we have won over the centuries, and some very touching images that are evidence of the emotions and passions the people of Siena live during the days that lead up to the Palio. During our visit I will explain in plain English how the contrada functions. I am grateful to the contrada for granting me this rare opportunity, and I’m equally honoured and eager to share this experience with you."

2016 All-inclusive price:
1-2 People: 257 EURO/group
3-6 People: 357 EURO/group


This private tour is available on request seven days a week. It lasts approximately three hours from the time you meet your guide in front of a centrally located hotel in Siena. Meals and transportation are not included in the price.