All Siena Tours &amp; Excursions in 2026 - page 11

Maremma Wine Experience: 5 Wines & Local Specialties

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.

from CA$50

Ultimate Walking Riddle Hunt in Siena

2 hoursFree Cancellation

4.0

from CA$99

Tour by Van to the Saturnia and Pitigliano Mill Falls

2 hours 30 minutesFree Cancellation

Hop on a full-day private tour to Florence and San Gimignano from Siena. Your adventure kicks off with a drive from Siena to Florence to explore the city center. Take a guided walking tour of the historic center and see key landmarks, including the Duomo, the Uffizi Gallery, and the Ponte Vecchio. Then, it's off to experience the medieval town of San Gimignano, known as the "medieval Manhattan."

(3)

from CA$124

From Siena to Florence & San Gimignano - Private Tour by Minivan

From Siena to Florence & San Gimignano - Private Tour by Minivan

9 hoursFree Cancellation

4.5

from CA$579

Discover Siena, a UNESCO World Heritage city, on a guided walking tour with a licensed local guide. Explore medieval streets, elegant piazzas, and Gothic landmarks while discovering the history, legendary Contrade, and traditions behind the world-famous Palio di Siena. Enjoy a traditional Tuscan aperitif with local specialties, freshly prepared bruschetta, regional cheeses, and a glass of Tuscan wine. Special Palio Experience – August 16 walking tour + Tuscan aperitif On August 16, experience Siena during its most iconic event. Your guide will explain the history and traditions of the Palio before accompanying you to Piazza del Campo and assisting you in entering the square before the crowds. Enjoy the spectacular Historical Parade (Corteo Storico), the Flag Throwers (Sbandieratori), and the unique atmosphere before the famous horse race. Please note: This experience includes guided assistance to access Piazza del Campo but does not include a reserved seat or grandstand ticket.

Siena Palio Experience: Walking Tour & Tuscan Aperitivo

Siena Palio Experience: Walking Tour & Tuscan Aperitivo

Direct Transfer from Hotel in SIENA to Hotel in ROME

(2)

from CA$232

2 hours 40 minutes to 3 hours 20 minutesFree Cancellation

from CA$1,346

This is an exclusive tour for you and your loved ones and, comfortably seated in the car you can enjoy the beauty of the places. In fact, we will see fascinating landscapes that are a little lost in time. In fact, the Maremma, in addition to being considered the new Eldorado for its powerful and elegant wines, offers wild and splendid landscapes. The typical local cuisine is Mediterranean. The people of Maremma are the most outspoken in Italy. Furthermore, the story I told will take us back in time to the Etruscans. As our ancestral ancestors did, you can, if you wish, take a thermal bath in the Saturnia waterfalls. New shower and toilet rooms available.

Exclusive Saturnia and City of Tuff

8 hoursFree Cancellation

from CA$636

Highlights - Historic Estate Tour: Guided 90-minute visit of Montechiaro Villa (since 1760), including the original wine cellar, aging rooms, and ancient olive mill. - Vineyard Walk: Self-guided stroll through scenic vineyards before or after your tasting. - Seated Wine Tasting: Enjoy four organic wines, including our signature Chianti and award-winning Super Tuscans. - Food Pairing: Traditional Tuscan delicacies perfectly matched with each wine. - Personalized Experience: Our expert Sommelier adapts the tasting to your preferences.

Wine Tour & Tasting - Organic Chianti & Supertuscan

Wine Tour & Tasting - Organic Chianti & Supertuscan

Discover the Siena of the soul during the Jubilee with a local guide expert in religious itineraries. The tour includes the following itinerary: Native places and history of the life of Saint Catherine, patron saint of Italy and Europe, you will visit San Domenico where his relics are preserved, the birthplace and the famous chapel where he received the Stigmata in front of a wonderful wooden crucifix. We will talk about Saint Bernardino of Siena, and we will see the exact point from which he preached to the Sienese in Piazza del Campo where the tile of the exact point is still visible. You will visit the splendid Basilica of San Francesco which preserves one of the most important Eucharistic Miracles in the world, namely the miracle of the Sacred Uncorrupted Particles. We will talk about the famous Blessed Ambrogio Sansedoni and San Bernardo Tolomei who founded the monastery of Monte Oliveto. At the end you will have a rich tasting of local products in a typical place, cold cuts-cheeses-oil-wine to also restore the body, after the spirit.

(1)

from CA$74

Exclusive Tour of Siena Santa with Rich Final Tasting

Exclusive Tour of Siena Santa with Rich Final Tasting

4 hoursFree Cancellation

Tuscan Wine Tasting and Local Cheeses

from CA$339

Maremma Wine Experience: 7 Wines & Local Specialties

3.7

(3)

from CA$60

Shared Val d’Orcia Bike Tour

from CA$58

4 hours

from CA$298

Discover Siena on an immersive walking tour through one of Tuscany’s most enchanting medieval cities, a UNESCO World Heritage Site. We discover the historic Palazzo Salimbeni, headquarters of the Bank Monte dei Paschi, and the city’s deep financial and cultural heritage. Continue through narrow medieval streets filled with artisan shops and local flavors. Visit the spectacular Piazza del Campo, famous for its shell shape and the legendary Palio horse race held twice a year. Admire the Palazzo Pubblico, Torre del Mangia, Loggia della Mercanzia, and Fonte Gaia while learning about the traditions of the city’s Contrade. The journey continues through charming alleys where you can find Tuscan specialties such as local wines and salami. The tour concludes with exterior views of the stunning Baptistery of St.Giovanni and the magnificent Duomo of Siena, masterpieces of white and black marble that define the city’s skyline. An experience that blends history, culture, and authentic Tuscan life

Siena Private Tour: Discovering the legendary Palio spirit

Siena Private Tour: Discovering the legendary Palio spirit

2 hoursFree Cancellation

from CA$551

Join our expert guide with your family on this kid-friendly, outdoor tour of Siena. You will discover the historic center, declared World Heritage Site, with its highlights, such as Piazza del Campo and Fonte Gaia, and discover the history of this beautiful medieval city. The guide will keep everyone involved with quizzes, trivia and games while sharing with you unique insights and commentaries about the landmarks of the town, including the Cathedral, Torre del Mangia and Palazzo dei Tolomei. You will also learn about the Francigena road and the life of Santa Caterina da Siena, one of Italy's patron saints. This 2-hour fun and informative tour will be a great way to explore the city, spend time with your children and play enjoyable activities. This will be a great way to live a memorable experience with the all family!

Kid Friendly Private Tour of Siena City Wonders for Families

Kid Friendly Private Tour of Siena City Wonders for Families

2 hoursFree Cancellation

from CA$37,214

Discover Siena's perfectly preserved medieval splendor with our self-guided audio tour app, allowing you to explore this Tuscan jewel at your own pace. Begin at the magnificent Piazza del Campo, the shell-shaped square that hosts the legendary Palio horse race and remains the heart of Sienese civic life after seven centuries. Marvel at the soaring Torre del Mangia and the Gothic grandeur of the Palazzo Pubblico, then ascend to the heavenly Duomo where Pisano's pulpit and the Piccolomini Library showcase Renaissance mastery. Wander through the contrade neighborhoods where medieval rivalries still define local identity, their fountains, flags, and parish churches marking territories unchanged for centuries. Discover the Pinacoteca's golden altarpieces and the Basilica of San Domenico where St. Catherine's head is reverently preserved, then lose yourself in the winding vicoli that reveal unexpected piazzas and artisan workshops.

Special Offer

At Your Own Pace: Discovering Siena & Tuscany

At Your Own Pace: Discovering Siena & Tuscany

9 hours 30 minutesFree Cancellation

from

CA$12

CA$2

Meet with tour guide at 10 am at Basilica San Domenico and departure for Pienza & Val d’Orcia Tour. A drive through a stunning landscape with its rolling hills, vineyards, olive groves that make unique the Unesco heritage territory of Val d’Orcia. We’ll stop to visit the Benedectine Monastery of Monte Oliveto Maggiore, stunning cicle of frescos, visit to the ancient library and Farmacy. Continuation to Pienza, the renaissance town born from Pope Pio the 2nd dream with its gorgeous architecture, narrow streets and terraces overlooking the Val d’Orcia. Time to stroll and visit craft made shops and enjoy a light lunch at typical farmhouse. Continuation to visit the stunning small hamlet of Bagno Vignoni with its thermal bath pool. Know before you go: Min. participants: 3 If the minimum number of participants is not met, the tour will be canceled or rescheduled, or you will be offered another available tour. You will be informed at least 16 hours before the tour date

from CA$372

Discover the beauty of Siena on a private walking tour through its most iconic landmarks, where medieval charm, art, and spirituality blend in perfect harmony. Your journey begins at Piazza San Domenico, closely tied to the life of St. Catherine, Siena’s patron saint. Just a short stroll away lies the Santuario Casa di Santa Caterina, a peaceful complex built around the birthplace of the saint. Nearby, you’ll come to Fontebranda, one of Siena’s oldest fountains. Your walk continues into the beating heart of the city: Piazza del Campo, a breathtaking shell-shaped square often considered one of Europe’s finest. Lined with graceful palaces and crowned by the Palazzo Pubblico and the Torre del Mangia, this is the stage for the world-famous Palio horse race. No visit to Siena would be complete without exploring the Duomo, a Gothic masterpiece adorned with black-and-white marble stripes, richly decorated interiors, and priceless works of art by masters such as Michelangelo.

Siena Private Walking Tour: Duomo & Historic City Highlights

Siena Private Walking Tour: Duomo & Historic City Highlights

3 hours

from CA$379

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition to it, this tour has an Arts footprint. We'll lead you through some hidden sculptures, located throughout the landscape, as a warm up to our stop at the Chianti Sculpture Park, where you'll visit some contemporary sculptures and installations. We'll build on to the arts experience by stopping at the hamlet of Scopeto, where the film "Letters to Juliet" has been shot. Least, but not last, it will be wine time right after at the Scopeto Winery, where you can further develop your reconnaissance of the territory by tasting one of its maximum expression: the Chianti Classico. We then, climb back to our comfortable ebikes to return to Siena

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

5 hours 20 minutesFree Cancellation

(2)

from CA$400

Embark on a one-of-a-kind adventure through the rolling Tuscan hills in a classic Fiat 500 – an authentic Italian icon. This rental offers a perfect blend of relaxation, nostalgia, and discovery as you cruise along scenic country roads, explore charming historic villages, and take in the beauty of vineyards and olive groves. What makes this rental truly unique is the combination of slow travel, vintage charm, and the chance to connect with Tuscany’s landscape and traditions at your own pace. Optional stops at local wineries offer opportunities to taste renowned Chianti wines right at the source (tastings not included). Ideal for couples, friends, or anyone seeking a memorable and stylish way to explore Tuscany, this tour combines freedom, authenticity, and the timeless joy of driving a vintage car.

Vintage Fiat 500 Daily Self-Drive Tour from Castellina in Chianti

Vintage Fiat 500 Daily Self-Drive Tour from Castellina in Chianti

9 hoursFree Cancellation

4.0

from CA$610

WHY CHOOSE US? Explore the beautiful city center of Siena at your own pace. This self-guided audio tour will take you to all the well-known spots and undiscovered gems of Siena. Go on a journey of discovery with your virtual audio guide and get to know Siena and its history in a unique way. - Walk at your own pace - The most beautiful walking routes and best stories - Unexpected discoveries - Route guidance via audio & GPS - Works offline and with phone in your pocket, hands and eyes free.

Siena: City Walk with Audio Guide in 7 Languages on your Phone

Siena: City Walk with Audio Guide in 7 Languages on your Phone

3 to 4 hoursFree Cancellation

Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.

from CA$13

Tuscany 3-Days 5-Cities Flexible Sightseeing bus tour

Tuscany 3-Days 5-Cities Flexible Sightseeing bus tour

3 daysFree Cancellation

4.5

from CA$115

Discover the enchanting landscapes, mouthwatering flavors, and intriguing history of Cortona and Montepulciano on a private day tour from Siena. This excursion is designed for travelers seeking an immersive and authentic sightseeing experience in Tuscany. As you marvel at spectacular vistas, savor tastings at renowned wineries, and gain insights into the towns’ Renaissance art, your guide will provide illuminating commentary that takes you out of the guidebook and into the heart of Tuscan culture.

Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings

8 hoursFree Cancellation

from CA$430

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s simple use as a vehicle. Ideal both on city’s tiny alleys and on the famous country-side windy roads. We will be visiting typical medieval villages, get in touch with local wine and food producers as well as artisans, and stop along the way to take some picturesque photos that will become indelible memories. An experienced tour guide will lead you around and show you the way as only a local can. The tour ends in a local farm where we will be hosted by a family that has been living there since centuries, producing their own wine, Chianti Classico. We will have the chance to visit the property including the cellar and then relax where a traditional Tuscan lunch will be served, all accompanied by their wines. Pick up and drop off from your accomodation in Siena included.

Private Vintage Fiat 500 tour in Chianti From Siena

5 hoursFree Cancellation

(1)

from CA$673

Private Luxury Olive and Wine off road tour

7 hoursFree Cancellation

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

from CA$455

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Top Attractions in Siena

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

Attractions

What are people saying about Siena

Noelle_S, Jul 2026

Fun date night dinner

My partner and I had a lot of fun with this cooking class and it met our expectations. We enjoyed learning how to knead the pasta dough and pressing out/ cutting the shapes for tortellini, tagliatelle and ravioli. It was a heat wave in Siena and the space had adequate A/C which was definitely necessary and appreciated as A/C is impossible to find in Siena. The food tasted just "ok" at dinner but the class had maybe 14 people in it all making the pasta so I wasn't expecting perfection. If you are a serious chef, this is not the class for you, you would need a much longer experience. They pasta ingredients are already in a bowl and you mix them together, knead the dough and make the shapes. You are not really cooking as you don't make the sauce or actually see the kitchen itself. That being said, it was the perfect length and type of experience for us. Red wine was served in jugs at dinner and plentiful. Water was served during the pasta making portion. The chefs were helpful and moved around the room to make sure everyone knew what they were doing. I would recommend this for couples looking for a fun evening or families with kids.

Siena: A Wine Tour and Tasting Experience

Amy_O, Jul 2026

A gorgeous afternoon in the Tuscan countryside

We really enjoyed this tour of the gorgeous La Lastra vineyard! Lorenzo was a great guide - knowledgeable and fun! The main house was beautiful and meeting one of their lovely little cats was an added bonus. The lunch served was delicious, and they asked about dietary requirements beforehand which was great as my partner and I are vegetarian. The tour was the perfect mix of laidback, low pressure and genuinely really interesting. You should definitely go here if you’re visiting Siena!!!

From Siena Best of Tuscany Wines and Lunch in Montepulciano

MELANIE_H, Jul 2026

Fabulous wine tour

Very full day visiting several Tuscan towns. Montepulciano, Pienza and Montalcino were all lovely and quaint. The winery in Montepulciano was amazing! Lunch and wines were fantastic! We did get lost and it was hard to get back in touch with our tour so make sure you take pictures and get phone numbers. Also, think about what you might want to buy in advance- you will have time for shopping!

Small-Group Tuscan Cooking Class with Wine & Lunch from Siena

Robert_P, Jul 2026

Amazing time. We...

Amazing time. We accidentally arrived 50mins early and our host didn’t mind a bit. He took my wife and I to the back yard and gave us beer from his personal supply and talked a while. The view was sensational. When everyone arrived we went into the room where the class was held. Our instructor made everyone feel relaxed and answered any questions that came up. After we made the pasta we had a small break to drink Chianti or beer and to get to know other people in the class. Then we made tiramisu. After that we had lunch which consisted of bruschetta, the pasta we made and finally the tiramisu. Can’t wait to come back and do it again!

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Zoe_N, Jul 2026

Wonderful Surprise!

Experiencing a long table for lunch with new found friends while tasting several wines & eating authentic Italian food was much more than expected. I even bought Biscotti & Pasta! Discovering Siena on foot, seeing the Cathedral & revisiting the history & learning the culture of the city is priceless!

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

Richard_B, Jul 2026

Fantastic tour

It was a really great wine tour, all 3 wineries were fantastic and the lunch was absolutely amazing. Pablo our guide was very informative and a really nice guy. We could not recommend this tour highly enough. We have done wine tours in Nappa valley and Santa Barbra before, this was our first in Italy 🇮🇹 and it was up there with the best. (Ps we are not American)

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Natalie_M, Jun 2026

A sensational evening to be had!

This experience was a highlight of our trip to Siena. Helene hosted our vineyard tour and chef-prepared, delicious 4 course dinner with generous paired wine tastings in excellent English, making the experience easy and very relaxed. The vineyard was easy to find and such a stunning and picturesque location, we felt we got great value for money and highly recommend.

Small-Group San Gimignano and Volterra Day Trip from Siena

Robert_T, Jun 2026

Tuscan Escapes - San Gimignano and Volterra

Ceco was an amazing guide for the day. The right amount of interesting history and facts delivered with passion and interest, balanced with sufficient time for self-exploration. Comfortable and safe vehicle to travel in. Small group made this souch more enjoyable and accessible. The lunch at Carmela's property was superb and just added to an already great day. Highly recommend Tuscan Escapes for the care they take and the passion they have for the Tuscan region (as evidenced by the high quality of their guides).

A Brunello Cooking Class with Vineyards View Winery

Stephanie_R, Jun 2026

Tuscan Experience

We had a great time at this cooking experience. We were greeted by Alice who gave us an informative tour of the castle and the winery. She was so kind and interested in sharing as well as answering any of our questions. The cooking part of our day was great. Yummy wine and fun Italian music was the perfect start to our lesson with Cat. We worked together with another family to create two kinds of pasta as well as tiramisu. While making, rolling and cutting our pasta, we were treated to a beautiful view out of the windows. After we completed our pasta, we sat down together to a lovely lunch (feeling proud to have made it ourselves) with more delicious wine. It was a fantastic way to immerse ourselves in the Tuscan life! Thank you for a fun day for our group.

Small-Group Montepulciano and Pienza Day Trip from Siena

Jennifer_H, Jun 2026

Our time in Montepulciano...

Our time in Montepulciano was one of our favorite days in Italy. Giovanni was an exceptional guide and he taught us so much about the wine and the area. We highly recommend Tuscan Wine Tours as they book small wineries. Our delicious lunch was at a dairy farm where we overlooked the gorgeous Tuscan region.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Desmond_R, May 2026

Awesome experience

It is a small bit of everything you'd want to experience at a vineyard ☺️. The guide and her team are friendly, helpful and happy that you are their guests. We enjoyed the small tour of history and the 3-course meal was a light delight. The wines were delicious 😋. Lovely experience for the price at hand.👌🏾