Top Siena Walking Tours

Skip the Line: Siena Duomo and City Walking Tour

Commence your journey at the iconic Piazza del Campo, immersing yourself in the vibrant atmosphere of Siena's renowned square. Delve into the city's history at Palazzo Pubblico, an architectural marvel serving as the seat of governance. Meander through historic streets, passing Palazzo Tolomei and Palazzo Salimbeni, both UNESCO-listed treasures. Continue to the Basilica of San Domenico, housing the relics of Saint Catherine, before a visit to the Sanctuary of St. Catherine of Siena. Admire the Baptistery and opt for a guided tour of the awe-inspiring Siena Cathedral, adorned with masterpieces of Italian artistry.

(745)

from $47

Siena Highlights Private Walking Tour With A Guide (Private Tour)

Siena Highlights Private Walking Tour With A Guide (Private Tour)

4.6

(30)

from $107

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.

Siena Private Highlights and Hidden Gems Walking Tour

Siena Private Highlights and Hidden Gems Walking Tour

2 to 6 hoursFree Cancellation

(5)

from $90

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

(257)

from $184

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 Walking Tour with Audio and Written Guide by a local

Siena Walking Tour with Audio and Written Guide by a local

4 to 5 hoursFree Cancellation

4.3

(37)

from $7

Siena has one of the most intact medieval cityscapes in Italy, and with this walking tour, you can take in the hill town’s top sights in just two hours. Skip the hassle of following a map and instead head straight to the highlights with a guide. Stroll past Piazza del Campo, the town hall, and the Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.

Discover Siena: Guided Walking Tour and Cathedral Visit

Discover Siena: Guided Walking Tour and Cathedral Visit

1 hourFree Cancellation

3.7

(36)

from $26

Private Tour: Secret Siena Walking Tour

(112)

from $332

Discover UNESCO-listed Siena through the eyes of a local on this custom-made Lokafy walking tour. Skip the typical guided tour and instead connect with a Siena local who will show you around their city like a friend and introduce you to the neighborhoods that they know and love. As you explore the city, gain an insight into Tuscan culture, cuisine, and everyday life; and receive recommendations on where to eat, drink, and shop.

Siena Private Walking Tour with a Local

2 to 6 hoursFree Cancellation

4.4

(12)

from $57

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. In case of religious celebrations or extraordinary closures (such as Sunday morning for Mass), the visit will be moved to the Antico Ospedale di Santa Maria della Scala, still guaranteeing a complete experience.

Siena : Siena Guided Tour with Duomo or Museum

1 hourFree Cancellation

4.3

(43)

from $42

When you’re in the Tuscan city of Siena, don’t miss the chance to discover its famous wines and enjoy some local food, too. This small-group wine tour visits a winery near Siena’s historical center, and gives the lowdown on the winery’s organic production methods. After visiting the vineyard, you’ll savor a meal made with local produce along with samples of five organic wine varietals. Numbers are limited to 12 per group.

Guided Winery Tour and Wine Tasting in Siena

2 hours 30 minutesFree Cancellation

Take a chance to discover Siena, a jewel of the Middle Ages set in the Tuscan hills, full of history and culture. Accompanied by a specialized guide of the city you’ll walk through the characteristic streets of Siena, admiring the beauty and the magnificent of Piazza del Campo where twice a year the horses run for the Palio race. You will learn about the world's oldest bank and the pilgrim's path as you discover the secrets of the famous 17 Contrade. The historic center is a UNESCO heritage site: the Cattedrale dell’Assunta is a gothic architectural work of art that will leave you breathless. You'll be amazed by the Duomo and by the heavy chimes of the Torre del Mangia that resound throughout Siena in its most important moments, especially during the Palio. Let’s discover together the myths, legends and secrets of this medieval town!

(66)

from $89

Private Siena walking tour

(5)

from $190

Indulge in Siena's culinary treasures on a private tour designed to delight your palate, led by an expert local guide. Stroll through charming cobblestone streets, where the enticing aromas from bustling food stalls beckon. Begin your epicurean journey with the crispy perfection of coccoli, drizzled with aromatic olive oil, and savor the multi-layered flavors of savory panini, each bite a testament to Siena's rich gastronomic heritage. As you meander through the city, your guide will share enthralling tales of Siena's history, blending tradition with modern culinary innovations. Discover how the city's vibrant food scene reflects its cultural tapestry, making this tour an ideal exploration for devoted foodies and curious travelers alike. Each stop unveils a new chapter in Siena's epicurean story, promising a memorable adventure that intertwines taste and tradition in the heart of this historic city.

Siena Street Food Tour With A Local Guide

Siena Street Food Tour With A Local Guide

(6)

from $101

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti’s rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

Chianti Half Day Wine Tasting Tour from Siena

Chianti Half Day Wine Tasting Tour from Siena

5 hoursFree Cancellation

4.4

(9)

from $58

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 Bites & Stories: A Tasty City Adventure with a Local

Siena Bites & Stories: A Tasty City Adventure with a Local

2 hours 30 minutesFree Cancellation

Discover the best of Siena’s traditional cuisine and food scene with the insights of a local insider guide on this small-group food tour. Set off with your foodie guide and group of just 12 fellow gourmands to visit the top artisan food shops, market stands, and other landmark eateries to sample a range of savory and sweet delicacies. Feast on charcuterie boards, pici pasta, ricciarelli cookies, and more as you explore the old town.

(19)

from $70

Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better

Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better

Siena Underground Wine tasting in a Medieval Cave

4.9

(219)

from $87

1 hourFree Cancellation

Private Tour: Siena Walking Tour

(56)

from $89

(49)

from $214

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.

The 17 Fantastic Animals of Siena

4.9

(16)

from $74

Siena is one of Italy’s most captivating medieval cityscapes, but its mazelike historic center is a challenge to navigate. With this private tour, explore with a local guide to cover the highlights in a few hours. Marvel at the Piazza del Campo, stroll the historic center, and take in the Basilica of St. Francis and Medici Fortress while you learn about the local history and architecture.

Siena Private Walking Tour With A Professional Guide

Siena Private Walking Tour With A Professional Guide

4.7

(3)

from $305

Explore Siena at your own pace with a self-guided walking tour on your phone. You get a clear map of all 12 stops, simple directions through Google Maps, and short audio stories you can play when you reach each location. The route covers Siena's historic center, from Piazza del Campo to Monte dei Paschi di Siena, passing sites like the Palazzo Pubblico, Torre del Mangia, and Fonte Gaia. Start anytime, pause whenever you like, and explore freely. No groups, no schedules. Audio and text available in 7 languages.

Self Guided Walking Tour of Siena

Discover with me the unknown and most fascinating Siena with this unique and unusual tour. SECRET SIENA WALKING TOUR, is my favorite to discover history, art and architecture of this wonderful medieval town,away from the crowded tourist routes. Uncover hidden squares, medieval alleys, 14° century perfectly preserved palaces, courtyards and ancient fountains with bewitching legends Enjoy the breathtaking views of Siena, perfect for unforgettable photos and peaceful and suggestive corners. Learn the stories about ancient noble families, medieval pilgrims and ancient disappeared monasteries Explore the territory of a Contrada to know the history of Palio race and visit, if you like, its private museum that I can book for you( tickets not included).

from $6

Secret Siena Walking Tour

(11)

from $267

Experience the enchantment of Siena with an enthusiastic local guide on this private tour. Discover famous sites such as Duomo di Siena, Piccolomini Library, and Piazza del Campo, while revealing secret treasures on your journey. This personalized, adjustable tour allows you to explore Siena in your style, featuring expert suggestions and captivating narratives that animate the city’s history.

Highlights & Hidden Gems of Siena Private Tour - Duomo Included

Highlights & Hidden Gems of Siena Private Tour - Duomo Included

(20)

from $230

Let our local guide guide you to discover the irresistible city of Siena, unique for having maintained its unmistakable medieval style intact. The main foundation of Siena's history, customs and popular traditions is the Palio, a horse race that takes place in the city twice a year, an event of great importance to the Sienese, who divide their supporters into contrade (districts) rich in legends, fervour and ancient symbols. The main attractions that our guide will show you during the tour are the splendid Piazza del Campo, with its characteristic shell shape, the majestic Palazzo Pubblico, the Torre del Mangia and the Fonte Gaia, a model of Renaissance sculpture. No less important, strolling through the alleyways of the centre, you will reach one of the most beautiful cathedrals in Italy, the Duomo di Siena. There are also alleys, narrow streets, ancient palaces, artisan shops, wineries and the many shops of the typical sweets of Siena: panforte, ricciarelli, cavallucci.

Siena: private 2-hours tour of the treasure chest of Tuscany

Siena: private 2-hours tour of the treasure chest of Tuscany

4.5

from $237

Private Guided Tour of Siena with a Licensed Local Tour Guide

(13)

from $134

Siena Underground Wine tasting in a Medieval Cave

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Top Attractions in Siena

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Attractions

What are people saying about Siena

Blake_H, May 2026

Wonderful Wine Journey

Frederico is amazing. A class act, truly. He gave us a wonderful tour of his shop and told us the story of how he was remodeling and a jackhammer fell through the floor and they discovered a tomb. An Etruscan tomb that later became his wine cellar, and it is magnificent. Although small, it has so many details. Frederico was patient and explained all of the wines, all of the regions, and how they can be different even if they're not that far from each other geographically. We tasted several great things and really believed that we were in the right place of the right time learning about all of it with him. We joined the wine club and are really excited to continue learning and savoring each and every bottle ahead.

Siena: A Wine Tour and Tasting Experience

Joseph_M, May 2026

A wonderful wine experience

Cristian was a fantastic host/guide! He was very knowledgeable about the wine growing, harvesting, and distillation processes. There was a great assortment of wines, perfectly paired with food & dessert. He and the staff also helped with getting taxis back to Siena train station, which was very kind and helpful. It was a great way to spend the day in Siena, have great food, and learn about wine.

Skip the Line: Siena Duomo and City Walking Tour

Joseph_A, May 2026

Elio to the Rescue!

Siena is stupendous! So a Siena Tour is a dream job for a Siena native, totally immersed Elio!!! Fantastic! Elio knows every nook and cranny of this Italian gem, and all 25 of our tour-mates felt the same way. Worth every hill and valley. Thank you Elio!!!

Siena Highlights Private Walking Tour With A Guide (Private Tour)

Henry_S, May 2026

Sienna Private tour review

Marianna our tour Guide was Wonderful! She educated us about the history of Sienna, was very knowledgeable and proud of living there and engaged with us during our private tour. Sienna is a truly Beautiful and diverse City to visit and a must for any Tuscany visit.

Tuscany Hiking Tour from Siena Including Wine Tasting

Donna_M, May 2026

A great and informative hike

Wonderful guided hike through the beautiful countryside: our guide Giovanni was excellent - educated us on the history of the area and the trail as well as the plant life. We wound up being the only ones on the tour the day we went. Wear good shoes - part of the trail is rocky. There are some inclines but overall a doable hike. We enjoyed the winery at the end and stayed there for lunch after the tasting. Thanks Giovanni for a grea lt morning. We learned so much

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Joshua_T, May 2026

Outstanding Tuscany Experience!

This was a fantastic day that we really enjoyed!! We learned a ton about the history of the region and how it’s been tied to wine making. Our guide Paulo was so nice, knowledgeable, and a joy to have as a host and driver throughout the day! Cannot thank him enough for a very memorable experience on our trip!! For sure book this trip if you can, as you will not regret it!

Discover the Medieval Charm of Siena on a Private Walking Tour

emma_t, May 2026

Siena Brought to Life

We had a truly lovely tour of Siena with Idania. She was warm, welcoming, and incredibly knowledgeable, happily answering all of our numerous questions. Because she lives in Siena, she was able to share not just the history but also what life is like in the city today, which made the experience feel even more personal and authentic. She guided us through fascinating historical sites and spoke with such passion that everything came to life. Her background in art history really showed, she wove in details and stories that we never would have discovered on our own. We ended the tour with one of her lunch recommendations, which was the perfect way to wrap up a wonderful morning.

Private Tour: Secret Siena Walking Tour

Susan_Y, Apr 2026

The absolute best! Must do!

This was probably one of the best tours we've been on. Georgia, our guide, was so much a great guide. She was very in tune with us too, knowing when she had to slow down her talking for my older mother who was not understanding and when to speed it up. She customized our tour with us and gave us so much history and lore, we fell instantly with Siena because of her. 10/10 best thing to do in Siena. Highly recommended!

Hot Air Balloon Flight Over Tuscany from Siena

Hanna_A, Mar 2026

Amazing

This was a great experience. My second time on a hot air balloon and it was just as amazing as the first. What a unique and peaceful easy to experience the Tuscan countryside. This team was very experienced with excellent communication before the experience and during it as well, and very friendly staff. The breakfast picnic after landing was perfect.

Hidden Castles & Chianti Wine Experience– Small Group

Christina_P, Nov 2025

Great guided experience with Luca

Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.

Tuscan Cooking Class in Central Siena

Paul_R, Oct 2025

A Tuscan Gem!!

Scuola di Cucina di Lella is a gem!!! From the moment we walked in the door we felt right at home. We were welcomed into this beautiful kitchen by Giulia and chef Francesco with open arms. They explained all that we will be making that evening and we eagerly got right into it. We made Pici (pasta), La Pappa col Pomodoro (soup), Chicken Escalopes, roasted potatoes, and Panna Cotta which all were mouthwatering .... even right now just thinking about them. The step-by-step process was so much fun because they made it fun. Asking for voluntaries I was able to get my mind, body and soul into knowing that we can create anything if you give yourself the space to do so. I was able to share the kitchen with chef Francesco and had so much fun because he made it fun and inviting for all to partake in. Once we got back home to the states my husband and I recreated this meal only 4 days after this class (which was recommended by Giulia after our meal) and had a blast doing so. The Pici is a work in process and will not give up in trying to create this very yummy pasta. The rest of the dishes came out perfectly!! This was our first cooking class ever and now that the bar has been set extremely high it will be difficult to compare others to it because of how perfect everything was. Thank you for making the end of our Italy Tuscany journey a special one to remember!! Ciao!!

Siena Walking Tour with Audio and Written Guide by a local

Michael_G, Aug 2025

Family Tour of Siena (family of five with 13, 10, and 8 year old kids)

Great experience walking through Siena. Audio guide gave great insight into various sites and website was very easy use. We went to Siena in August so it was very warm. The self paced audio guide was nice because we could take breaks whenever we wanted and start back up at any point within the tour.