Top Siena Walking Tours

Siena Mysterious Holistic Audio Tour between Legends and Secrets

5 hoursFree Cancellation

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$17

$14

Private Tour: Secret Siena Walking Tour

Discover the island of Siena at your own pace with this guided tour. With a tour of more than 2 hours, you can explore Siena discovering monuments such as Piazza Tolomei, Via Citta or the Duomo of the city. This option without schedules or groups allows you to enjoy the city flexibly, including recommendations on gastronomy and family activities. Available in six languages, this experience is ideal for those looking for hassle-free personalized tourism. - 2h self-guided tour with + 15 points of interest - Access to information in 6 languages: Spanish, English, Portuguese, French, Italian and German Explore iconic attractions and receive food recommendations. - No groups or schedules, ideal for traveling at your own pace.

TOP Siena : Private Guided Tour with your mobile

2 to 3 hoursFree Cancellation

Savor the flavors of Siena on this delightful food tour, where you’ll explore the culinary treasures of Tuscany. A local guide will lead you through the charming streets, sharing fascinating insights about the region’s food and wine culture. Enjoy tastings of sparkling wine, red wine, gelato, pecorino cheese, cured meats, pizza and traditional sweets like cantucci and panforte. This small group experience ensures an intimate atmosphere, perfect for food lovers looking to immerse themselves in authentic Tuscan cuisine. - 2 - hour walking food tour through Siena’s enchanting streets - Taste a variety of local Tuscan products - Learn about the history and culture of Siena’s culinary scene - Enjoy a small group setting for personalized attention from your guide

Siena Food Tour : Local Tuscan Flavors

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

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.

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

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

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and Taste’ will introduce you to the local food and wine and to the fascinating world of sustainable wines. A journey through the secrets of viticulture in the age of climate change. Designed for all those who love fine wine and food, this intimate experience is for a maximum of 8 people and is led by one of the winery's owners. The winery tour will be followed by a guided sensory tasting session to capture and break down the different organoleptic profiles that participate in the complexity of our vintage and private reserve wines. Finally, you will enjoy a full lunch with the right food and wine pairings that will delight your palate and nourish your soul.

Exsclusive Wine Tour and Tasting in Siena

Exclusive Wine Tour and Tasting Experience in Siena

3 hours 30 minutesFree Cancellation

Explore Siena’s historical highlights and iconic cathedral on a private walking tour of the historic center. This short but comprehensive tour is designed for curious travelers who want to maximize their limited time in this Tuscan city. As you admire Piazza San Domenico, Torre del Mangia, and other local treasures, your guide will provide illuminating commentary that takes you out of the guidebook and into medieval Tuscany.

Siena Private Walking Tour: Traditions, Streets & Cathedral

2 to 3 hoursFree Cancellation

Explore the mysterious, magical world of truffles, wander through the woods in the company of a local expert truffle hunter and his dogs and enjoy a unique and direct experience of this ancient tradition. Truffles are a seasonal delicacy but in this area we are very lucky, in spring we can find the Marzuolo or March truffle, in summer the Tartufo Nero Scorzone, a black Summer truffle, while in winter there are black winter truffles but also sometimes the famous " Bianco delle Crete Senesi", the highly prized white truffle. Outside our farm house we meet up with our expert truffle hunter and his wonderful dogs. To help you get the best of the companionship of the truffle hunter, a mine of information on truffles, the dogs, the woods and countryside and the local area in general you will be accompanied by an English speaking interpreter - generally an interpreter who also assists in the cooking classes and so able to give you tips on storing and using the truffles in the kitchen.

Truffle Hunting in Tuscany

Two magic hours to discover the city with Your children! Children and adults will learn the city's history having fun and being enriched by anecdotes and legends from the Middle Ages! Magic is hiding in plain sight.... Stroll around the streets of Siena to discover the mysteries, reach the ancient castle and discover the symbol of Siena, the she-wolf, which from the top of its columns protects us. Learn about the 17 districts that we call Contrade and find the animals that represent them. The Contrade participate to the horse race twice a year, an incredible event! Have fun to watch the videos, find the stables where the horses sleep for four days and the little fountains hidden through the streets where the Sienese are baptized.

Siena Family Tour

Hidden Castles & Chianti Wine Experience– Small Group

5 hoursFree Cancellation

Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

4 hoursFree Cancellation

The city of the Palio runs on rivalry — ideal conditions for a scavenger hunt. This app-led scavenger hunt takes you through Siena on foot, using phone-based riddles to guide you from one landmark to the next. No guide, no fixed start time. • Decode the marble stories of the Battistero di San Giovanni • Sweep into Piazza del Campo, the shell-shaped stage of the Palio • Stand before the striped magnificence of Siena's Duomo Available in 24 languages including English, French, German, Spanish, Italian — see the full list when booking and choose yours when you start the game in the app. Around 2 hours - any group size. Seventeen contrade, one leaderboard.

Siena Self-Guided City Walking Tour & Scavenger Hunt

Discover Tuscany's stunning landscape, culinary delights, and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Avoid the hassle of driving yourself and be led by a local guide. Admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with a visit to a winery.

Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

Italian Opera in Siena Experience

1 hour 20 minutesFree Cancellation

The Chianti Hills are a must-visit for wine lovers in Tuscany—and this small-group winery tour offers an immersive introduction to the region's vinous delights. Pick a start time that's best for you, make your own way to Castellina in Chianti, and explore a wine estate whose history dates back centuries. Then, enjoy a guided tasting of four premium wines, all paired with local olive oil, focaccia, cheese, and cured meats.

Chianti Classico wine Tour and Tasting

1 hour 30 minutesFree Cancellation

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

Tuscany Hiking Tour from Siena Including Wine Tasting

4 hoursFree Cancellation

Explore the enchanting streets of Siena in a unique way through a walking riddle hunt. This interactive adventure invites participants to uncover the city's fascinating stories and hidden gems at their own pace. Wander through iconic spots like Piazza del Campo while solving puzzles and challenges that reveal the rich history of this UNESCO World Heritage Site. With professional guides available for hints, this treasure hunt-style experience is perfect for families, friends, and curious travelers looking to engage with Siena's culture in a fun and dynamic way.

Ultimate Walking Riddle Hunt in Siena

Shake up your sightseeing routine and skip the bland group tour with this app-based quest that leads you through Siena’s medieval center via engaging puzzles and challenges. Solve clues as you stroll through the old town at your own pace, learning about the city’s history and taking in landmark sights along the way. Delve into the power struggles between Siena’s ruling families in the Middle Ages and admire the squares, churches, and palaces they built.

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Siena Medieval Power Quest: Self-Guided Family Feud Game

Siena Medieval Power Quest: Self-Guided Family Feud Game

1 hour to 1 hour 30 minutesFree Cancellation

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Opt for a personalized experience of Siena’s top attraction on a private tour of Siena Cathedral. With just your private guide and party, discover easy-to-miss details in the cathedral’s interior and benefit from commentary integral to understanding the statues of Michelangelo and the art inside the Chapel of St. John the Baptist. Plus, booking in advance means you save hours of waiting in line with a skip-the-line admission ticket.

Private Tour of Siena Cathedral

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!

Private Siena walking tour

Widely considered among Siena’s top attractions, Siena Cathedral dates back to the 13th century—but the cathedral’s medieval history is easy to miss. On this tour, explore Siena Cathedral with your private guide and see the best of this impressive Sienese landmark in one comprehensive visit. Hear the hidden history behind artworks by Bernini, Donatello, and Michelangelo, and admire key features such as the baroque chapels and marble façade.

Siena Cathedral: Private Tour

1 hourFree Cancellation

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 walking tour with Gelato & Prosecco

1 hour 30 minutesFree Cancellation

The Tuscan countryside is a premier hiking destination, but navigating unfamiliar trails and country roads on your own can be daunting. On this private hiking tour, explore the rolling hills and vineyards stress-free with a guide leading the way. Meet in Siena and transfer to the trailhead by minivan, setting off through the verdant countryside and past rustic villages. Take a break to relax over a classic lunch of Tuscan treats and then travel via minivan to San Gimignano for a stroll through town and along a stretch of the Via Francigena before the return ride to Siena.

Private Tour: Guided Hike in Tuscany with Transport from Siena

7 hoursFree Cancellation

Siena: A Wine Tour and Tasting Experience

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Must-Dos in Siena

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The magnificent Gothic and Romanesque structure of Siena Cathedral (Duomo).

What are people saying about Siena

John_L, Oct 2026

We recently took a wine...

We recently took a wine tour here, and to say it exceeded our expectations is an understatement. From the moment we arrived, the atmosphere was incredibly welcoming, warm, and sophisticated yet entirely relaxed. The estate boasts stunning, panoramic views that are worth the visit alone—make sure your phone is charged because you will want to take a lot of photos! Our host, Lorenzo, was absolutely fantastic. He was incredibly thoughtful, attentive, and his deep knowledge of the winemaking process made the tour both insightful and engaging. He didn't just rattle off facts; he shared genuine insights that gave us a whole new appreciation for what goes into every bottle. The wine tasting itself was outstanding. Each pour was excellent, beautifully paired, and generously served. Lorenzo guided us through the notes of each wine in a way that was accessible but highly informative. Everything about this day was perfect, from the breathtaking scenery to the immaculate hospitality. If you are considering booking this tour, do not hesitate—it is a flawless experience!

Skip the Line: Siena Duomo and City Walking Tour

Mattea_K, Oct 2026

We loved our tour with...

We loved our tour with Giulia! She is a Siena local, she was very passionate and knowledgeable about local history and culture. We only had a few hours in Siena so it was nice to get some background about the city. The trip inside the Duomo was lovely as well, Giulia’s explanation of different parts of the church made it more interesting that we could understand the history and images.

Tuscany Hiking Tour from Siena Including Wine Tasting

Sandra_J, Oct 2026

This was an outstanding...

This was an outstanding experience. The guide, Giovanni, is also a naturalist, and in the way he explained different plants and other things we were seeing. He was friendly, witty, and very knowledgeable. The map we were given for the bus back to Siena was confusing, but he helped several of us locate the bus stop.

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

Jane_S, Oct 2026

A wonderful way to spend an evening

This class was excellent. Francesco provided many valuable general cooking tips that can be used apart from the specific dishes that we were taught to make. Julie's English translation was invaluable in helping us understand Francesco's instruction (and jokes). And finally, the five course meal that we had at the end was very enjoyable.

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

Amar_P, Oct 2026

This is a beautiful wine...

This is a beautiful wine immersive experience! Our guide Paolo was beyond amazing with his personality, knowledge, and passion for Italy and the region! We heard great stories of wine, family and tradition from all 3 wineries visited, none were tasting rooms in the city but a true vineyard experience

Hidden Castles & Chianti Wine Experience– Small Group

Keith_C, Sep 2026

Great way to fill in an afternoon in Siena

Our tour guide was caught in traffic from Florence, but we were kept informed. It wasn't a small group, we had about 25. The tour was fantastic with plenty of time at each stop. It went overtime, which was excellent value for money. Our guide was a little shy with limited English, and could have given more info en route. Overall... woukd recommend.

Siena Street Food Tour With 4 or more Tastings

Michael_N, Aug 2026

The best tour and guide you will ever have!

Veronica was the best guide we have ever had. We’ve traveled the world and have gone on many tours, high-end, on the lower side, in the middle. She is the absolute best and went above and beyond all of our expectations. Even after the tour, she was extremely accommodating and made us feel like a local. I would never use anyone else ever. Absolutely 10 out of 10 the best you’re gonna get.

Hot Air Balloon Flight Over Tuscany from Siena

Tal_W, Aug 2026

Breathtaking Experience and View of Tuscany

This was hands down one of the most memorable experiences of my life. The company went out of its way to find a location to ensure more optimal weather for the ride. It was so serene to fly up and down and see Tuscany from air. The ride was incredibly smooth as was the landing. This was a bucket list experience for me and it delivered. Would absolutely recommend booking this ride.

Siena Underground Wine tasting in a Medieval Cave

Ronald_J, Jul 2026

One of our best wine tasting experiences.

This is amazing experience in which the owners discovered the cave by accident in a shop they purchased. All temperature controlled. Francesca and her husband are a devoted and very knowledgeable couple. Don't miss this wine tasting experience and history of the Tuscan wine region specifically in Siena.

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.

Siena Private Walking Tour with a Local

Steven_O, May 2026

A one of a kind tour of Siena

Giacomo guided me on a solo tour of Siena this afternoon and it was my best tour so far. He took me outside the city center to see some to other smaller churches and a spectacular view back to Siena from the north. He was very knowledgeable but also added in some of his personal experiences growing up there. It was fantastic and I highly recommend him as a guide. Steve