Siena
Walking Tours

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Our most recommended Siena Walking Tours

Florence Cathedral: Tour with Cathedral Terraces and Brunelleschi's Dome

1. Florence Cathedral: Tour with Cathedral Terraces and Brunelleschi's Dome

Explore the marvels of the Santa Maria del Fiore Cathedral in Florence with an expert guide. Learn about the cathedral's construction and artworks, and admire breathtaking views over the city from Brunelleschi's Dome. Begin with a guided visit of the interiors of the magnificent Santa Maria del Fiore Cathedral. Avoid wasting time waiting in the ticket line and enter the Duomo accompanied by a licensed guide. After your quick entry, discover the superb works of art preserved inside the cathedral.  Then, enjoy the chance to go to one of the cathedral's exclusive terraces, where you can take in the magnificent scenery surrounding you, dominated by the amazing Brunelleschi's Dome. Find out about the techniques Brunelleschi used to create this architectural wonder. Without any additional waiting in line, climb even higher up to the magnificent Dome to enjoy a spectacular 360-degree view of Florence.

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Siena: City Walking Tour with Optional Siena Cathedral Tour

2. 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. 

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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.

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San Gimignano, Siena, Chianti Guided Tour from Florence

4. San Gimignano, Siena, Chianti Guided Tour from Florence

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

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Siena: Medieval Legends Exploration Game

5. Siena: Medieval Legends Exploration Game

Discover the top attractions and landmarks in Siena in a unique way by playing a city exploration game on your smartphone. Visit some of Siena's most famous sites, such as the Palazzo Tolomei, Fonte Gaia, and Piazza del Duomo. Download Questo, the gamified travel app, onto your smartphone, and begin your exciting exploration game. Assume a role in an ancient political fight between the Salimbeni and Tolomei families. Take part in a historical struggle for the control of Siena, and fight for the cause of a third family, the Terrazini. Find out secrets about the Salimbeni and Tolomei families that you can use to harm them. Stay out of the spotlight, and provoke the two families to start a war against each other. Solve a clue to reveal exact directions to your next stop on the tour, without the need of a map, GPS, or a physical guide. Each solution reveals a secret story about Siena's main attractions, such as the Banca Monte dei Paschi di Siena, the second oldest bank in the world. Complete the tour at your own pace, and pause and restart the tour whenever you please. After purchasing the quest, an access code will be delivered to your email, which can then be used in the downloadable app. If you are a large group, one person can purchase access for the entire group by selecting the number of people in the group. All group members will be able to play the city game on their smartphone. Alternatively, each person can purchase their own ticket. You can play as a group and solve the clues together as you walk, or you can split into smaller groups/teams and compete against the others. Each person can also play on their own, separate from the group, and meet the group at the end.

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Historic Siena: Guided Walking Tour

6. 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.

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

7. 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 world-wide 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 also the Palazzo Tolomei, said to be the oldest private palace in the city as well as the Basilica di San Domenico, Rocca Salimbeni, Palazzo Chigi Saracini, and other historical buildings. See 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 Renaissance busts of popes and emperors, and marvel at the unique black-and-white-striped bell tower.

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Siena: Guided Nighttime Walking Tour

8. Siena: Guided Nighttime Walking Tour

Meet your guide after dusk, then set off on a 2 hour adventure through Siena. Walk through the city’s bustling streets and see a selection of famous landmarks including Piazza del Campo, Siena Cathedral, and the Torre del Mangia. Along the way, listen to your guide’s fascinating tales of the city’s history and culture as well as the noble families and prominent historical figures who still haunt the streets.  You’ll also discover some of the city’s hidden gems, and visit locations only the locals know about. By the end of the tour, you’ll have seen Siena from an entirely new perspective.

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Florence: Siena and San Gimignano Day Trip

9. Florence: Siena and San Gimignano Day Trip

Boarding your air-conditioned coach in Florence, you will meet your tour leader who will stay with your group for the duration of your day trip. As you journey through the rolling hills, vineyards and olive groves of the Chianti region, they will tell you what to look out for in each new town. Your first stop will be the medieval town of Siena, where the Palio horse race has been held twice a year since the 17th century. A local guide will join you for a tour through the red-brick streets to the Duomo di Siena. Exquisitely faced and floored with marble, this grand cathedral also houses sculptures by the young Michelangelo. Take the time to breathe it all in, before your tour continues to the Piazza del Campo. It is at this exact location where twice a year, jockeys representing Siena’s wards compete fiercely (and not always fairly) for glory. As you listen to your guide’s tales of victories and defeats, it will be easy to imagine the piazza filled with the thunder of horses hooves. Back aboard your coach, you will spot the iconic tower houses of San Gimignano on the skyline from miles away. This Medieval walled town will be yours to explore, as you wander back in time along the narrow streets, being able to ask your tour leader where to find the best gelato. After enough free time to explore and take pictures, rejoin the group for your complimentary glass of Chianti wine and some nibbles. The coach will then return you to Florence.

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

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

Join a small group or private walking tour to discover Siena’s famous monuments and hidden treasures with an expert guide. Enjoy skip-the-line entry to Siena Cathedral and explore tucked-away squares and gardens. Meet your guide at the San Domenico Basilica. First, follow a winding route to take in panoramic views of the city, including the Duomo and Torre del Mangia. Continue your tour with the 14th-century seashell-shaped square, Piazza del Compo, a UNESCO World Heritage site. Then, learn the history of the "contrade" (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. Find out about Siena in the Middle Ages and the local pastry that reflects these glory days. Make sure to ask your guide where to find the best local bakery that still uses centuries-old recipes to make traditional Ricciarelli and Panforte. Next, admire the magnificent Fonte Gaia fountain with its side reliefs of "The Creation of Adam" and "The Flight from the Garden of Eden." Finally, skip the line at Siena Cathedral. 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, you will say goodbye to your guide in the square in front of the cathedral.

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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

We enjoyed the whole experience. We booked this wine tasting in winter, probably not the ideal season cos the weather is so unpredictable and the vineyard is not in its full bloom but despite that we had fun learning about the history, the process and the wine tasting itself. Our guide/host Ilaria is very warm, welcoming and very knowledgable. She considered us, being beginners, during the whole tour, so she explained the basics and everything in layman’s term. It was a very interesting and wonderful experience. We learned a lot and ordered a few wines to take home cos they tasted that good.

Best way to see Florence! Our guide Carmen was amazing and so knowledgeable, she tailored our tour to accommodate to a slightly slower pace since my parents couldn’t walk too fast. She answered all the questions we had along the way and even provided tips for places to go see on our own during the rest of our visit in Florence. Her voice was very soothing and easy to listen and my family and I enjoyed spending the day with her exploring the city. Entrance to the museums was faster and the galleries were even more interesting and enjoyable thanks to our guide. Will definitely recommend!

Mateo met us at the appointed time in an easy to find location. His commentary and insights during the visit to the Accademia were focused on a select group of artworks and permitted a more in-depth enjoyment of the selected works, of course, Michelangelo's David being a centerpiece. The access to the terrace during our Duomo visit was a special treat as well as the visit to the top of the dome. 3 and 1/2 hours well-invested.

We learned so much from our wonderful guide. Everyone in our family enjoyed this tour.

Excellent guide. He was able to underline the important aspects.