Best Siena Walking Tours in 2026

Siena , Tuscany

From $ 46.54

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 $ 87.27

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 $ 87.27

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 $ 75.63

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 $ 72.14

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 $ 6.97

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 $ 6.98

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 $ 72.14

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 $ 68.65

To fully discover a city one may participate in a lot of tours and go eat at many venues published on travel guides and recommended by online travellers but the true local knows where to take you and you'll be paired with a Local Expert who will tell you stories, curiosities and will take you to spots outside of the tourist lens. We'll visit the most important and the least acknowledged hitspots of the Medieval Centre of Siena. Also, with us, you'll be able to eat some of the most typical snacks available in the city and taste the local Tuscan Wines, which mean a lot to the gastronomic history of the locals. The activity is suitable to people of all ages, from the kid discovering the curiosities behing the walls of the centre to the adults learning about Siena's culture.

Siena , Tuscany

From $ 72.14

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 $ 64.00

This is a city walking tour that will give you the occasion the see this city from the eyes of a local. Your Guide is a certificate professional that has lived and worked in Siena for many years and can give you a full immersion view on the traditions of the city. We will discover together the myths, legends, and secrets of this medieval town and we will have the occasion to see very iconic neighborhoods and street where normally locals spend their time with friends and family. You will try 3 different flavors of Artisan Gelato & Tuscan wines. At the end of the tour our guide if requested will give you some great recommendation like the best restaurants or any other activities to do in Siena.

Siena , Tuscany

From $ 55.85

Skip the standard sightseeing tour and discover Siena through the eyes of a local. With Lokafy, every tour is private, unscripted, and personalized to you. Your Lokafyer is a passionate local who shares stories, hidden gems, and authentic tips you won’t find in a guidebook. They aren’t professional guides with memorized scripts, they're locals who love their city and want you to experience it like a friend would. Whether you’re interested in food, art, history, or simply exploring the neighborhoods beyond the tourist spots, your Lokafyer will adapt the walk to your interests. By the end, you’ll feel at home in the city, with insights to keep exploring on your own.

Siena , Tuscany

From $ 72.14

Our Polaguides will allow you to discover the most hidden, but no less fascinating places than Siena and its districts and instant photography will allow you to appreciate the beauties of each district 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. During the days of the Palio (29 June-2 July and 13-16 August) the 17 Fontanine di Contrade 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 $ 75.63

Discover the authentic beauty of Tuscany with our tour of vineyards, art and flavours. We begin with a walk through the vineyards, immersed in the heart of Chianti, to reach the charming little church of San Giorgio a Lapi, dating back to 1100. Here you can admire three splendid frescoes by Nasini, a true hidden gem. After the visit, we will enter our cellars to discover the winemaking and aging process of the wine. And to end in style, a tasting awaits 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 $ 88.77

This walking tour offers a truly local take on Siena, far beyond the postcard views. With your host, you’ll explore hidden chapels, medieval backstreets, peaceful gardens, and the living traditions of the Palio and contrade. Whether you're tracing the path of a district rivalry, admiring Gothic architecture, or sipping wine in a tucked-away enoteca, this is your chance to explore like a local, not a tourist. After booking, you’ll receive a short questionnaire to share your interests and travel style. Based on your responses, you’ll be matched with a like-minded host who will contact you directly to suggest a personalized itinerary. You’ll agree on a meeting point and time, and your route can adapt throughout the day based on what captures your interest.