Best Walking Tours in Siena 2025

Siena , Tuscany

From $ 47.80

Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and visit the stunning Siena Duomo (Siena Cathedral) with your fast-track, skip-the-line entrance ticket. As you walk through this incredibly beautiful Tuscan city with your expert guide, you'll feel as though you’ve journeyed back in time.

Siena , Tuscany

From $ 101.58

In the hills of the gorgeous Tuscan countryside,  just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine and Life' is a 3-hour tour held in an organic winery. Learn about the different stages of wine making through the seasons and enjoy tastings and a light lunch.

Siena , Tuscany

From $ 108.75

Siena is one of Tuscany's best-loved cities, a fixed stop for those in the Chianti region. A destination for many visitors, Siena is internationally known not only for its picturesque, medieval historical centre, the famous Palio di Siena in Piazza del Campo and the colourful countryside that surrounds it, but also for the delicious cuisine it offers. It is impossible not to think of the excellent dishes and exquisite wines that can be found in the city. Thanks to our gastronomic tour of Siena, we will discover together the secret dishes and recipes of the Sienese tradition.

Siena , Tuscany

From $ 101.58

I will take you for a wonderful walk and show you historical Cafes, local deli, mediaeval alleys, secret medieval caves and the "the oldest bank of the world". The main attraction are: - The lookout where you will see the entire city - Piazza Salimbeni - Piazza del Campo - Piazza Tolomei - Panoramic View of the Cathedral - Traditional food tasting with Chianti & Prosecco On this tour you will try some local food and wine like the famous Chianti, Pecorino cheese, bruschetta and homemade pasta known as pici. We will discover together the myths, legends, and secrets of this medieval town and see iconic neighborhoods and streets where locals spend their time with friends and family.

Siena , Tuscany

From $ 95.60

•Discover the highlights of Siena on a walking tour and enjoy skip-the-line tickets for the Cathedral Complex. •Enhance your experience with an extended tour of the Cathedral Complex, Crypt, and the Museum. •Explore medieval Siena on a guided walking tour and learn about the history behind the famous Palio horse race. •In a small group, marvel at the architectural highlights that dot Siena's skyline, including the renowned Duomo.

Siena , Tuscany

From $ 89.63

For real wine lovers, This is a wine tasting experience hosted by a Sommelier. This tour offers you an exclusive wine tasting in a Medieval cave dating back to Etruscan period, 600 BC. This place is private and the only one accessible to public. Here you will have one of a kind experience tasting the best wines selection from Sienna's region. Brunello di Montalcino is also in the list of top 100 best wines in the world by the magazine Wine Spectator. Our Licensed Tour Guide will give you an introduction about Sienna history and assist you during the tour giving some tips on where to eat and what do in town during your stay. Please note: This experience being the a private premises is limited to 12 people per day.

Siena , Tuscany

From $ 89.63

Winery Tour and Wine Tasting in Siena with Afternoon Meal. Immersed in the magical atmosphere of rural Tuscany, just a stone's throw from the old town of medieval Siena, the experience is a journey into the history, culture, tradition, and science that give life to every bottle of our organic wine. During the winery tour we will analyze together the characteristics of the vineyard agro-ecosystem and the techniques used to preserve and regenerate rural resources. In our old wine cellar, we will take you through the fascinating world of winemaking and the secrets behind crafting quality wine. The tour will end in our tasting room, where you will grasp all the organoleptic nuances of our young and vintage wines. Each glass will be paired with the best seasonal Tuscan products, to delight your palate and nourish your soul.

Siena , Tuscany

From $ 47.80

Splendid Classic Siena Tour with guaranteed departure from Via di Città at 11am in English and at 12.15pm in Italian. An expert local guide will introduce you, in an interesting and pleasant way, to the history of Siena, the Duomo, Piazza del Campo and other monuments of the city. We will talk about the Palio, the districts and visit the lesser known and quieter corners of the city. Including entrance ticket to the Duomo and Palazzo delle Papesse. The expert guide will accompany you inside the Duomo or the Palazzo delle Papesse, subject to availability. On days of religious celebrations or extraordinary closures of the Duomo (such as Sunday morning for Mass), the tour will be adapted to ensure a complete experience. Access to both monuments is included in the package, and you can also visit them independently during the rest of the day. The entrance to the Duomo also includes access to the splendid Piccolomini Library, located inside.

Siena , Tuscany

From $ 74.09

If you are looking for a unique and fun activity to involve the whole family in the interactive discovery of the most hidden but no less fascinating places in Siena, you cannot miss our Treasure Hunt! Furthermore, instant photography will allow you to appreciate the beauties of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be customized, to be browsed whenever you want. Find out all the details, solve the puzzles and answer the quizzes to transform your visit to Siena into a unique memory to share with the whole family, young and old, and with friends. N.B. In the days of the Palio (29 June-2 July and 13-16 August) the treasure hunt route is not feasible and is replaced with that of the Top 10 dedicated to the places of the Palio, of which we will provide a dedicated guide and map.

Siena , Tuscany

From $ 7.41

Unravel the secrets of medieval Siena through a thrilling quest of power, rivalry, and hidden history. This isn’t just a walk - it’s an adventure through time. Guided by your phone, you’ll follow in the footsteps of Siena’s powerful families as you solve 9 clever puzzles tied to the city’s most iconic landmarks and lesser-known corners. You’ll explore places like Fonte Gaia, Piazza del Duomo, Palazzo Tolomei, and even the world’s second-oldest bank - all while uncovering the dramatic story of a family’s rise to power during the Middle Ages. Every solved clue reveals another piece of the city’s rich history. What makes this tour unique? It blends real-world exploration with a historical escape game, letting you experience Siena not just as a tourist, but as part of its medieval drama. Perfect for families, couples, or solo travelers who love history, mystery, and a bit of strategy. Play at your own pace, offline or online—no schedule, no pressure.

Siena , Tuscany

From $ 71.70

Discover the authentic beauty of Tuscany with our tour of vineyards, art and flavors. We start with a walk through the vineyards, immersed in the heart of Chianti, to reach the picturesque church of San Giorgio a Lapi, dating back to 1100. Here you can admire three splendid frescoes by Nasini, a true hidden jewel. After the visit, we will enter our cellars to discover the winemaking and aging process of the wine. And to top it off, a tasting is waiting for you on our panoramic terrace, overlooking the Crete Senesi, accompanied by a lunch with the best typical Tuscan products, all in the shade of an ancient white mulberry tree. Live an unforgettable experience between nature, history and good wine!

Siena , Tuscany

From $ 74.09

Our Polaguides will allow you to discover the most hidden, but no less fascinating places than Siena and instant photography will allow you to appreciate the beauties of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be customized, to be browsed whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends. N.B. In the days of the Palio (29 June-2 July and 13-16 August) the normal route of the Top 10 in Siena is not feasible and is replaced with that of the Top 10 dedicated to the places of the Palio, of which we will provide a dedicated guide and map.

Siena , Tuscany

From $ 6.57

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the support of a local, you will be able to visit all the most important monuments at your own pace: Piazza del Campo, the Duomo, Basilica di San Domenico and much more! You'll get to know the stories and curiosities of Siena! But also you will discover everything about local foods, Italian aperitivo in authentic local restaurants, and much more! What are you waiting for?

Siena , Tuscany

From $ 74.09

If you are looking for an activity that combines a visit to a special city of art like Siena with fun for the whole family, with particular attention to the little ones, you just have to try this PolaTour! By reading the guide you will enter directly into a fairytale world that will allow adults to discover the city with new eyes and children to explore Siena through the places in the heart of the 17 Contrade. Discover the places where the indissoluble bond that binds every Sienese to their district is created: the fountains! Will you be able to find all the fantastic animals? Immortalize them with an instant photo and keep them in the PolaGuide! N.B. In the days of the Palio (29 June-2 July and 13-16 August) the path of the 17 Fantastic Animals is not feasible and is replaced with that of the Top 10 dedicated to the places of the Palio, of which we will provide a dedicated guide and map.

Siena , Tuscany

From $ 92.02

Come and discover Siena and its incomparable historic centre with our morning walk that aims at showing you the main attractions but also discovering some hidden gems. You can understand this wonderful medieval city in many ways and taste some of its best local products.