Siena Walking tours

Our most recommended Siena Walking tours

Siena: Guided City Tour with Cathedral Skip-the-Line Entry

1. Siena: Guided City Tour with Cathedral Skip-the-Line Entry

Explore the beauty of Siena on a small group or private walking tour. See its famous monuments and hidden treasures with an expert guide. Benefit from skip-the-line entry tickets to Siena Cathedral. Meet your guide at the San Domenico Basilica and admire its Gothic architecture. Follow a winding route to take in panoramic views of the city, including the Duomo and Torre del Mangia. Find out about Siena in the Middle Ages, see the imposing palaces said to be the oldest in the area. Have a break to take in the charm of the 14th-century seashell-shaped square, Piazza del Compo, a UNESCO World Heritage site. Admire the magnificent Fonte Gaia fountain with its side reliefs of "The Creation of Adam" and "The Flight from the Garden of Eden." Learn about the history of the contrada (districts) that challenge each other twice a year during Siena’s Palio horse race. Walk to one of the most typical contrada and immerse yourself in the authentic atmosphere. Follow your guide to see one of the local pastry shops that reflect the glory of Italy in using the centuries-old recipes to make traditional Ricciarelli and Panforte. Finally, explore one of the most fascinating cathedrals in Italy with pre-reserved tickets. Follow your guide to marvel at the magnificent marble mosaic inlay floor, stained glass, and medieval masterpieces by Duccio and Pisano. See the Renaissance highlights: several Donatello, Michelangelo, and Bernini sculptures and frescoes by Pinturicchio in the Libreria Piccolomini. Armed with a wealth of knowledge about Siena, say goodbye to your guide in the square in front of the cathedral.

Historic Siena: Guided Walking Tour

2. Historic Siena: Guided Walking Tour

See the highlights of Siena on a walking tour as your guide tells you about the development of the city over the centuries and you enjoy the spectacular scenery and monuments. As you visit Siena’s major attractions such as the central Piazza del Campo, the Palazzo Comunale, the Cathedral, and the majestic Basilica of San Domenico you’ll learn about each of these sights in depth from your guide. You’ll also hear about the noble families that were instrumental in the history of the city, including the Piccolomini, Tolomei, and Salimbeni, and see their palazzos. You’ll learn about the great tradition of the palio and hear stories of pilgrimage and saintliness that distinguish Siena. You can decide to finish the tour with a visit to Cathedral where numerous artistic treasures are preserved. Entrance to the Cathedral is available at an additional cost. You’ll see works by artists such as Pisano, Duccio di Buoninsegna, Donatello, Pinturicchio, and Gianlorenzo Bernini. During the summer you can also see the marvelous marble floor, which is a unique work in the history of art.

Total Immersion Wine Tour in Chianti

3. Total Immersion Wine Tour in Chianti

All the guests will be welcomed at the estate and brought to the roof of the cellar to see the most breathtaking views of the rolling hills at 600 meters above sea level. Here one of the passionate members of the team will provide an introduction to a history of the estate and a small general explanation of what guests will see and what they will be doing in the next one and a half hours of their time. Clients will be able to visit one of the vineyards followed by an explanation of the working process and of organic agriculture with some additional biodynamic techniqes that are often used and practised at the estate. If the weather permits, guests would be offered a glass of sparkling wine or a fresh wine of their choice at the small adjecent terrace built under an oak tree.  The tour will then take everyone to a visit through the gardens of the villa and include a visit of the vegetable garden. The cellar is the next stop, where detailed explanation follows about the harvest and selection of the grapes during the harvest, fermantation, and further aging of the wines. Each step of the viniticulture process is explained in great detail and guests would learn a lot of new and exciting things about how to make wines in the Chianti Classico area. The last stop is a tasting room, where guests will be able to try all 5 products of the estate with the selection of various local cured meats and/or cheeses with bread and olive oil. Guests will also learn particular details about the history of each wine, will learn how to smell and taste it, and what to look for when opening a new bottle of wine. The last exciting detail is the grappa, for those who would like to learn about its production and unique and delicate taste.

Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets

4. Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets

Discover the beauty of Siena during a 2-hour walking tour. One of Italy's loveliest medieval cities, it is known worldwide for its Palio, the country’s most spectacular festival that features a wild bareback horse race around Piazza del Campo, the central square. Visit Siena's historic center, a UNESCO World Heritage Site, and marvel at the magnificent architecture of the Palazzo Comunale and the Palazzo Tolomei, said to be the oldest private palaces in the city. See the Basilica di San Domenico, Rocca Salimbeni, Palazzo Chigi Saracini, and other historical buildings. Admire the imposing stone tower of Palazzo Chigi Saracini, built by the powerful Marescotti family in the 12th century. The building is now the seat of the prestigious Accademia Musicale Chigiana, founded in 1923.  Take a walk to St. Dominic's Basilica, built entirely of brick, and admire its Gothic architectural style. Continue your tour to one of the most spectacular cathedrals in Italy, the Duomo of Siena.  Your guide will escort you inside the cathedral, where you’ll see impressive masterpieces by Donatello, Bernini, and Michelangelo. Admire the exquisite Gothic architecture, walk through the arcades with busts of popes and emperors, and marvel at the unique black-and-white-striped bell tower.

Siena: City Walking Tour with Optional Siena Cathedral Tour

5. Siena: City Walking Tour with Optional Siena Cathedral Tour

Explore Siena's rich history, culture, and traditions with a local guide. The tour is designed to show you Siena's most intriguing sites in a short period, with plenty of stops for photos along the way. Start the tour with a visit to some of the city’s most significant sites including the Piazza del Campo, Palazzo Publicco, Palazzo Tolomei, Palazzo Salimbeni, and the ancient Banchi di Sopra. Upon exploring, learn which buildings hold UNESCO World Heritage-listed status and why. Continue the tour to the Basilica of San Domenico, which is home to Saint Catherine's relics. Next, stop by the Sanctuary of St. Catherine of Siena, where she once lived with her family. Pass by the Baptistery and the Siena Cathedral (or the Duomo di Siena), and head inside for a closer look (if the optional guided tour option is booked). Inside, admire the array of works of art from some of Italy’s most important artists. 

Siena: Palio Walking Tour

6. Siena: Palio Walking Tour

Learn about the unique history of Sienna on a walking tour of the medieval old town with an informative guide. Get to know the different "contrade" or districts that make up the city and hear how they date back to medieval times. Stroll through the Piazza del Campo, where the famous Palio horse race takes place every year on July 2nd and August 14th, featuring a contestant from each of the contrade. Visualize the colorful banners and crests of the competing contrade and learn how the competition has defined civic life in the city for centuries. Hear stories about the life and culture of the city from locals and visit the Museum of the Contrada for a more official account. Then head to the Duomo of Siena and check out the characteristic black and white marble interior of the cathedral designed to symbolize the black and white horses of the city's founders. Afterwards, switch gears and enjoy a local tasting experience at a traditional cafe. Try Panforte, Ricciarelli, and Cavallucci, typical sweets famous around the world. Wash them down with a glass of Vin Santo del Chianti.

Chianti: Wine and Olive Oil Tasting with Cellar Tour

7. Chianti: Wine and Olive Oil Tasting with Cellar Tour

After arriving at the Fattoria Santa Stefano, your tour begins with an introduction to the grounds and history of this charming farmhouse. After learning about the building’s construction and local food and wine production, you’ll enter the farmhouse’s large wine cellar, featuring stainless steel and cement tanks used for the fermentation of their delicious Chianti wines. Then, it's time to visit the small and rustic 18th century cellar, home to the large barrels of French oak where the wine gets transferred and remains for six months to develop its rich and vibrant flavors. In the same cellar, you’ll also find the little barrels used for the production of Vinsanto, a delicious, amber-colored local dessert wine. To finish off the tour, see the farmhouse’s impressive “Orciaia”, where the extra-virgin olive oil is stocked directly after harvesting and pressing. From there, head back into the small wine shop to enjoy a tasting of some of the excellent local wine varieties and delicious extra-virgin olive oil, along with some great local food.

Siena 2-Hour Private Guided Walking Tour

8. Siena 2-Hour Private Guided Walking Tour

The beautiful city of Siena is famous not only for its beautiful and historical buildings and the picturesque landscape surrounding it, but also for its cuisine, art, museums, medieval cityscape and of course the Palio, the famous horse race held here twice a year. Take part in this private guided tour of the city and see its highlights, while your guide tells you about the development of the city over the centuries and you enjoy the spectacular scenery and monuments. You will visit Siena’s major attractions such as the central Piazza del Campo, the Palazzo Comunale, the Cathedral, the majestic Basilica of San Domenico, the Battistero of San Giovanni and much more! Prepare to take amazing pictures of the palaces, the "piazze", the typical streets of the old town and the picturesque hills all around you.

Siena: 2-Hour Private Walking Tour

9. Siena: 2-Hour Private Walking Tour

See the artistic, religious, and cultural treasures of Siena on a 2-hour guided walking tour. Discover the best of the city on foot as you listen to your guide's explanation of local history, traditions, and noble families.  As you wander around the streets of this ancient town, discover how its glorious past is still present in the beauty and elegance of its palaces and squares, along the ancient pilgrim's route called 'Via Francigena' - The French Way. During your tour, visit the main sites, such as Piazza del Campo, where the famous horse race Palio takes place twice a year, and the Duomo square, with its amazing marble striped cathedral. You will also have the opportunity to get off the beaten track and discover some of the lesser-known sights dotted throughout the medieval neighborhood.

Siena: Food and Culture Guided Walking Tour

10. Siena: Food and Culture Guided Walking Tour

Take a guided walk through Siena's history and food culture with a guide on this walking tour. Discover the medieval historic center and try some local specialties. Your experience begins at the main entrance of the Church of San Domenico. This is an important place for Siena and its people because it holds the relics of Saint Catherine, the Patron Saint of Italy. Walk through the medieval historic center and admire the charming architecture. Learn about the history of Siena from your guide along the way. Let the narrow alleys of the city lead you to the Piazza del Campo. Marvel at this shell-shaped square which is home to the majestic Palazzo Pubblico. Taste some "ricciarelli," a sweet local specialty, at your first food stop. Continue on to your next tasting at a local wine bar and try an Italian panino stuffed with your favorite ingredients and paired with a glass of wine. Afterward, admire the Gothic cathedral and the medieval pilgrims' hospital, which has attracted many pilgrims to Siena throughout the centuries. End your tour with some gelato at a local ice cream shop.

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Frequently asked questions about Siena

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What are the best day trips and excursions from Siena?

The best day trips and excursions from Siena are:

San Gimignano

Other Sightseeing Options in Siena

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What people are saying about Siena

Overall rating

4.2 / 5

based on 1,994 reviews

Idiana was terrific, charming, knowledgeable and answered our many questions with a smile, she made the tour fun and interesting. She had a very easy way about her and easily transitioned to highlight key places and history of Siena pointing out specific things to really heighten out tour

A delightful few hours learning about wines and food from area. Ambra was personable and animated as she talked to us. We loved the intimacy of the group..

Really good female guide who lives in Siena, speaks good English and knows the local history + short cuts. Very good, interesting + knowledgeable tour

Elena was an excellent guide and really helped us get a better understanding of Siena.

This was a great tour and it was a great way to see Siena!