Top Siena Walking Tours - page 3

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

Private Tour: Guided Hike in Tuscany with Transport from Siena

(6)

7 hoursFree Cancellation

from $381

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.

PolaTour The 17 Fountains of the Contradas of Siena

(7)

1 to 4 hoursFree Cancellation

from $74

Florence Duomo Cathedral Guided Tour from Siena

7 hours 40 minutesFree Cancellation

from $88

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

(2)

from $191

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.

from $169

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.

Hunt for the 10 Treasures of Siena

4.9

(39)

1 to 4 hoursFree Cancellation

from $74

1 hour 30 minutesFree Cancellation

from $214

Explore the artistic heart of Tuscany with this Florence Walking Tour from Siena. Experience a scenic train ride to Florence, where you'll discover iconic landmarks such as the Cathedral of Santa Maria del Fiore, Piazza della Signoria, and the historic Ponte Vecchio. This guided tour brings the city’s rich history to life, revealing hidden gems and engaging stories about the Renaissance. Enjoy free time to wander and soak in the vibrant atmosphere of Florence, making this a perfect day out for art lovers and history enthusiasts alike. - Scenic train journey from Siena to Florence included - Guided walking tour featuring major landmarks and hidden gems - Free time to explore Florence at your own pace - Ideal for those comfortable with walking and stair climbing

Florence Walking Tour from Siena with Train Tickets Included

7 hours 40 minutesFree Cancellation

from $77

Visit to the Farm and walk with the Alpacas

1 hour 30 minutesFree Cancellation

from $54

Visiting our farm means exploring a historical reality of the Tuscan Maremma, a traditional family farm - which today has been able to transform itself into a 4.0 company based on the concept of circular economy. A journey between tradition and innovation. The route of the guided tour shows the entire sustainable supply chain of the company: from agriculture for the production of buffalo feed to cattle breeding in large outdoor fenced areas; from the production of milk to its transformation into cheese in the company dairy; from the use of agricultural waste to produce renewable energy in a biogas plant to reuse the process residue as an organic fertilizer.

Visit to the Bufale and Dairy farm with cheese tasting

4.6

(14)

1 hour 30 minutesFree Cancellation

from $77

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).

Secret Siena Walking Tour

4.8

(11)

from $268

Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

San Gimignano, Chianti, and Montalcino Day Trip from Siena

4.3

(150)

11 hoursFree Cancellation

from $167

Half-day Private Walking Tour of Siena

(2)

from $441

A two hours enchanting walk, discovering Siena most beloved places. Start in front of the Basilica San Domenico, where the relics of St. Catherine are kept, then continues towards her ancient house. Stroll in the characteristic streets and reach the Cathedral. Decide with your guide if you want to enter shortly to see the unique marble floor and artworks by Donatello, Bernini and Michelangelo. Arrive at the famous Piazza del Campo, the main square, where the Palio (horse race), takes place twice a year. Discover this medieval tradtion and understand why it is so important for the Sienese. The Town Hall is an example of Italian architecture, which houses the important city museum. Admire also the Joyfull Fountain and listen to funny anecdotes about the mysterious river called "Diana". At the end of the tour visit our location in an historic palace, Palazzo Scotti, where you can take amazing pictures from our exclusive windows overlooking Piazza del Campo. Relax and enjoy your time!

Siena Tour and exclusive window on Piazza del Campo

4.8

(40)

from $208

Siena Sightseeing Walking Tour with Food Tastings for Small Groups or Private

(16)

2 hours 30 minutesFree Cancellation

from $143

Capture your memories of Siena on camera during this private photo shoot in the heart of the city. Bookable for a group of up to five people, the experience is led by a professional photographer with knowledge of the best backdrops around the beautiful city of Siena. Bring any additional clothing, shoes, or accessories to make the most of your photo shoot. After the shoot, take home a collection of quality digital images to impress friends and family back home.

Private Photo Shoot in Siena

(4)

1 hour 30 minutes

from $417

The perfectly intact medieval center of Siena is stuffed with important historic sights, and it’s hard to know where to begin. Get your bearings and touch on the top attractions in just a few hours with this private walking tour. Stroll through the cobblestone streets with a guide so you can focus on the architecture rather than a map and marvel at highlights like the Piazza del Campo and cathedral.

Siena Private walking tour

(4)

from $262

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

4.7

(3)

from $306

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

(20)

from $231

Siena Historic Center (Siena Centro Storico) is a UNESCO World Heritage Site for its glorious Gothic architecture and rich culture. Join an official, licensed guide who specializes in the city and understands it deeply on this in-depth tour. You'll see the signatures: Piazza del Campo, home of the annual horse race, and Siena Cathedral, with its marble stripes. But you'll also delve further into Siena's medieval neighborhoods and local lifestyles.

2 hour Siena Private Guided Walking Tour

from $393

Siena lovers, you will get the chance to breathe the atmosphere of the life of the Contrada and the Palio of Siena! An exclusive opportunity! An exciting experience lived with its protagonists: the Sienese people: vising the Museum and the Church of the Contrada Our guide will also lead you through the Piazza del Campo, where the most famous Palio in the world takes place every year on July 2nd and August 14th. We will also visit the Duomo of Siena, a gem set in a jewel city! We will continue to move into the world of the purest tradition with a tasting of typical Sienese sweets: Panforte, Ricciarelli and Cavallucci accompanied by Vin Santo del Chianti. These products, famous all over the world, maintain a high quality offered to the public in the past hundred years! The family of singer Gianna Nannini has been producing these sweets for generations and iat Caffè Nannini twe will stop and taste these specialities.

510

Vip Siena Palio Tour!

from $336

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills. In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.

Private Grape stomping in Chianti from Siena

5 hoursFree Cancellation

from $461

The entire historic center of Siena has been declared a World Heritage Site, if you desire to feel the atmosphere of a unique medieval town this is the place to be, you will effectively walk in a giant, open-air museum celebrating the Gothic style. This 3 hour walking group tour is ideal for first-time visitors or those short on time, our English- speaking tour guide will lead you to discover the beauties and stories of this picturesque medieval town. You will learn about the Francigena road, the ancient route that in medieval times connected Canterbury to Rome, understand the Contrade way of think and the importance of the Palio, admire gothic buildings and cathedrals, see the oldest bank in the world, discover fossils imprinted in marble, unravel the mystery of the Sator magic square. At the end of the tour you will feel transported in another time and will desire to spend more time immersed in this gothic dream.

Highlights of Siena Private City Tour with Local Guide

3 hours

from $273

Guided Winery Tour and Wine Tasting in Siena

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Top Attractions in Siena

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What are people saying about Siena

Leslie_S, May 2026

Don’t Miss this Experience!

Absolutely perfect afternoon! Lorenzo was so knowledgeable, warm & friendly. We learned so much about the vineyard life and winemaking in general. The vineyard is beautiful, the tasting was exceptional, the food was an unexpected delight and the company was engaging. We made new friends, tried 5 wines and then dessert with a dessert wine. One of the best tour experiences we’ve ever had. Highly recommend to anyone looking for a wine experience! Say hi to Lorenzo!

Tuscany Hiking Tour from Siena Including Wine Tasting

Jean_B, Apr 2026

Beautiful, educational and delicious.

This is a leisurely stroll through the Tuscany countryside. During the hike, the guide teaches participants about the history of castles, the history of the pilgrimage you experience (you are walking 5 miles of the Via Francigena; which begins in Rome and ends in Canterbury) and the importance of many of the trees, plants and herbs along the trail. The guide departs at this point; giving bus tickets to return to Siena. Participants then do get a small Chianti wine tasting. There is a lunch table prepared outside and participants can choose small plates to eat while choosing a wine to drink. The food and wine is not included; this is an additional cost. Giovanni was a wonderful guide; friendly, knowledgeable and very passionate about his culture and the natural environment.

Discover the Medieval Charm of Siena on a Private Walking Tour

Jeffrey_G, Apr 2026

Siena tour - Not to be Missed!

Highly recommend this tour! Barbara was a wonderful tour guide! Very knowledgeable about Siena, having grown up in the area. It’s a fabulous city not to be missed! And the surprise at the end made us all fall in love with Siena that much more! Spectacular view! Thank you, Barbara!!

Siena: A Wine Tour and Tasting Experience

Lauren_D, Apr 2026

A Must Do Experience at La Lastra in Siena

An absolutely amazing experience at La Lastra. The winery is charming and full of character. The tour was very informative and engaging covering information on the vineyards, wine making process and wine cellar. The wine tasting was delicious and the homemade lunch was a perfect pairing with the wine selections. Shipping wine home to the US rather than carrying through Italy and the airport was trouble free. Thank you Lorenzo and the entire staff at La Lastra!

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!

Skip the Line: Siena Duomo and City Walking Tour

Ruthann_C, Apr 2026

Highly recommend!

I so wish I could remember our guide’s name. He was fantastic! He did a thorough job telling us all about Siena. He was very knowledgeable and had a great sense of humor. His English was great and easy to understand. At the end of the tour, he gave us great recommendations for dinner and gelato. Two thumbs up!! Siena is a very hilly little town, so be prepared to walk alot of hills on this tour.

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

Marie_M, Mar 2026

Anita was fantastic. She...

Anita was fantastic. She kept us thoroughly entertained as she walked us through the history of Siena then gave us a feel for local life in Siena today. She provided wonderful restaurant recommendations as well as suggestions for additional things to do and tours to consider. This was one of our favorite activities while in Siena

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

Karon_M, Mar 2026

Excellent Wine Tour and Guide

This small group wine tasting was the highlight of our trip! Our tour guide Georgia was amazing. We had the most delicious wines at a small vineyard and the best food ever by a chef (and winemaker) at one of the other vineyards. It was nice to also visit a local town and abbey. This tour (and Georgia) should not be missed!

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!!

Hot Air Balloon Flight Over Tuscany from Siena

Marita_L, Oct 2025

Absolutely an experience not to miss

They do a great job in making sure that the flight will be safe, gauging the weather and letting you know if it has to be canceled or moved to a new location. While a new location can be inconvenient it is for your safety. I appreciate the care they take. The experience was extraordinary. The staff was very helpful and they treat you with kindness and respect.

Siena walking tour with lunch & Chianti wine

Chris_C, Oct 2025

Our tour guide Mohad was...

Our tour guide Mohad was incredibly knowledgeable, not only about Siena’s history but also about all the food, wine and gelato places. Some of them truly hidden gems! Perfect mix of walking tour and tasting of local specialties, all within 3 hours and away from the big tourist areas. I would highly recommend this tour!

Hidden Castles & Chianti Wine Experience– Small Group

Donna_W, Jun 2025

Great Tour for sightseeing and wine tasting

Great tour. The castles and the wineries were great. A lot of different wines to taste, but also gained knowledge of the region and the winemaking process. Just one warning. If you get car sick easily, make sure you bring your remedy. The roads are curvy and bumpy.