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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 pre-reserved 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.

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

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

Discover the beauty of Siena during a 2-hour walking tour, one of the world's most well-preserved medieval cities. Walk the narrow cobblestone streets and marvel at the architecture. Visit the Basilica di San Domenico and learn more about St Catherine, patron of Italy. Learn about the grand history of this proud Republic and discover the traditional Palio, a spectacular festival that features a wild bare-back horse race around Piazza del Campo, the city's central square. Learn about the Contrade or city neighborhoods and how they wait all year to participate in this fundamental race. Visit Siena's historic city center, a UNESCO World Heritage Site, to marvel at the magnificent architecture of Palazzo Salimbeni, today the world's oldest Bank, attesting to the wealth and trade of its glorious past. See Palazzo Tolomei, an imposing private Gothic building and the main square with its monuments and fountain. Discover the culinary traditions of the town and finally walk to one of the most spectacular cathedrals in Italy, the Duomo of Siena.  Your English-speaking local tour guide will escort you inside the Siena Cathedral to visit the chapels and to see the impressive masterpieces by Donatello, Michelangelo, and other artists, an unforgettably rich building of centuries of art and devotion.

Historic Siena: Guided Walking Tour

3. 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

4. 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: 3h Private City Walking Tour with Optional Cathedral

5. Siena: 3h Private City Walking Tour with Optional Cathedral

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: Food and Wine Walking Tour

6. Siena: Food and Wine Walking Tour

Walk around Siena and discover its best foods while meeting local vendors. Learn about the region's wine production and taste a typical white and red wine. Taste local wines at the Tuscan Wine School and learn about the local production of cheeses, cold cuts, and extra virgin olive oil. Walk around Siena to discover its best foods while meeting local vendors. Learn about the region's main products and how they are connected to local history and tradition. Discover more about the Cinta Senese and how local truffles are found. Follow your guide to discover why the Tuscan bread is historically plain and saltless, how it is used in recipes today, and the medieval recipes behind the traditional.

Siena: Private City Highlights Walking Tour

7. Siena: Private City Highlights Walking Tour

Siena is one of the most loved and most visited medieval cities in Tuscany, a place rich in history and art, but also in strong traditions, mainly linked to the contrade and the famous Palio di Siena. Siena is one of the best preserved historical cities in Tuscany, still surrounded by walls, created as a work of art that blends into the surrounding landscape. The city of Siena is a medieval jewel made of bricks and stones that houses dozens of Gothic palaces, churches and squares of enchanting beauty. Together with your guide, you can enjoy a private tour to discover the beauties this city has to offer, such as Piazza del Campo, where the Palio takes place, the 102-metre-high Torre Mangia, Fonte Gaia, and many other masterpieces to admire as you stroll through the narrow streets of this Tuscan gem.

Siena: Civic Museum Private Tour

8. Siena: Civic Museum Private Tour

With this 2hour guided tour of the Civic Museum you will discover one of the major Italy museums. Inside Palazzo Pubblico an expert guide will explain you the frescoes, created by some of the most important 14th-century artists, such as Simone Martini, Duccio di Buoninsegna and Ambrogio Lorenzetti. Within the exhibitions, you will see artistic works from the 14th up to the 19th century, offering you a complete overview of the evolution of Sienese art. Your guide will lead you to discover the heart of Sienese Art — the Civic Museum inside the Sienese town hall. Once inside the Civic Museum you will be introduced to the beautiful 19th-century frescoes in the first room of the museum, dedicated to Italy’s Risorgimento (unification), and you'll discover the medieval World Map Room, with the masterpieces of Simone Martini, la Maestà, and il Guidoriccio da Fogliano. Finishing your visit in the Peace Room, where you'll find the famous depiction of Siena, and the Allegory of Good and Bad Government, by Ambrogio Lorenzetti, one of the first examples of civil art. The subject of the painting is not religious, but rather represents Utopia in Siena and explains the difference between the good and the bad government.

Chianti: Wine and Olive Oil Tasting with Cellar Tour

9. 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: Walking Food Tour with Tastings

10. Siena: Walking Food Tour with Tastings

Enjoy a rich meal (lunch or dinner) within the city of Siena on a guided food tour. Learn about each dish you taste as you visit local restaurants, cafes, and historic eateries. Discover what the local cuisine has to offer. Try some of the best food in Siena and learn a little bit about the local culture along the way. Here's a list of possible tastings: Charcuterie and cheese board - Taste the best charcuterie and cheeses from the area accompanied by a good glass of local wine. Pici cacio e pepe or with wine - Pici senesi are made in a way that respects ancient processes, such as bronze wire-drawing. You can taste them seasoned with cacio e pepe or with wine. Pappa senese - of peasant origin, the recipe has been handed down from generation to generation. With a small detail that differentiates it from the traditional Tuscan pappa al pomodoro. Ribollita - the typical soup made of bread and vegetables, delicious! Tonno del chianti - an ancient Tuscan recipe made with pork, purged for days in coarse salt and then cooked 5 hours in white wine and herbs. Ricciarelli - Marzipan biscuits in the shape of a grain of rice with a crunchy, wrinkled and cracked surface coated in sugar and a grainy interior that is soft to the bite... delicious!

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Frequently asked questions about Siena

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The best day trips and excursions from Siena are:

San Gimignano

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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..

Wonderful guided tour around Siena; helpful to do your first day to get you oriented.

Great tour in a beautiful city! Would definitely recommend to anyone!

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