All Siena Tours &amp; Excursions in 2026

Skip the Line: Siena Duomo and City Walking Tour

(692)

Free Cancellation
2 hours

from $47

Sample Italy's flagship Brunello di Montalcino wine in the hills where it’s produced with this exclusive winery tour and tasting at a medieval castle. Join a sommelier for a stroll through the vineyards to learn about the history and production of Brunello at this family-run estate, then relax over a tasting that pairs three different wines with local specialties. Cap off your experience with a three-course Tuscan lunch.

(7)

E-Bike rental in Tuscany

Free Cancellation
1 day

from $53

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

4.6

(94)

Free Cancellation
1 hour 30 minutes

from $69

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

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

(955)

Free Cancellation
9 hours

from $223

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

(87)

Free Cancellation
3 hours

from $87

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

(55)

Free Cancellation
2 hours 30 minutes

from $88

4.5

(172)

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

Free Cancellation
11 hours

from $93

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.

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

(204)

Free Cancellation
3 hours

from $86

Hidden Castles & Chianti Wine Experience– Small Group

4.5

(173)

Free Cancellation
5 hours

from $58

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)

4.7

(20)

Free Cancellation
3 hours

from $106

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

(281)

Free Cancellation
8 hours

from $223

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

4.2

(31)

Free Cancellation
4 to 5 hours

from $7

Siena: A Wine Tour and Tasting Experience

(355)

Free Cancellation
3 hours

from $100

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

(3)

Free Cancellation
5 hours

from $58

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

(3)

Free Cancellation
2 to 6 hours

from $89

Siena: Small group Cooking Class in Chianti Farmhouse

(162)

Free Cancellation
4 hours

from $135

Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

(1)

Free Cancellation
2 hours

from $82

Get views you can't find anywhere else on this hot-air balloon ride over Tuscany. Starting in Siena, float above the countryside and take in scenic views of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) and enjoy seeing the countryside and surrounding ancient villages and towns. Upon landing, enjoy a glass of sparkling wine to celebrate your experience.

Hot Air Balloon Flight Over Tuscany from Siena

(130)

Free Cancellation
3 hours

from $364

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

(3)

Free Cancellation
3 hours

from $100

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

(112)

Free Cancellation
4 hours

from $70

Tuscany and Pisa have always been synonymous with rich and fine food and there are many and varied aspects of the city that you can discover with our food and wine tour. Along with the locals, who live the city every day, we will take you to the city’s most popular and historic places and we will make you try the real “pisano” taste and flavours: starting from the typical rural tuscan salamis and cheeses, to the traditional focaccia “cecina” (from italian “ceci”: chickpeas), to conclude with an ice cream in one of the historical ice-cream stores in the city. If you want to really enjoy Pisa food tradition walking downtown and entering in restaurants that only local people know, join our Pisa food tour!

Pisa Traditional Food Tour

Free Cancellation
3 hours 30 minutes

from $140

The academy is much more than a cooking school where you can learn traditional dishes, it is an authentic experience that blends tradition, local flavors and Tuscan hospitality. We stand out for the careful selection of ingredients of the territory, many of which are zero km. Position is the very framework of experience. Immersed in the medieval streets a few steps from Piazza del Campo, it gives our guests a unique and suggestive atmosphere where every experience is accompanied by the beauty of Siena.

Tuscan, Italian, tiramisu cooking class and tasting 3 wines

(8)

Free Cancellation
3 hours

from $100

Spend your day through the picturesque Tuscan landscape on an original Vespa scooter, enjoying peaceful roads that wind through the rolling hills of Chianti. This unique experience allows you to immerse yourself fully in the sights, scents, and sounds of the Tuscan countryside. As you navigate the winding roads, take in panoramic views of vineyards, olive groves, and ancient farmhouses dotting the landscape. Midway through your excursion, make a stop at a renowned winery nestled in the heart of the Chianti region. Here, indulge in a delightful wine tasting experience, savoring the flavors of locally produced wines that have been crafted with passion and expertise. After replenishing your energy, discover hidden gems off the beaten path, uncovering the rich history and culture that define this beloved region.

Free Cancellation
4 hours

from $128

4.7

(67)

Italian Opera in Siena Experience

Free Cancellation
1 hour 20 minutes

from $38

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Top Attractions in Siena

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Attractions

What are people saying about Siena

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

Heather_B, Feb 2026

Great experience

My husband and I did this class during our short stay in Siena and had a great experience. We did the 1030 AM class figuring we could have lunch as part of it - and I'm so glad we did lunch. We were so full at the end! It was good to walk around a bit after. We ended up being the only 2 people in the class which was fun. The instruction was great and everything was set up and ready for us. Once we made the 3 different pastas and the tiramisu, we went down to the restaurant to eat it. We ended up not being able to finish it all and were thankful for a to-go box (it made for a great dinner later!). We also were able to get the recipes (on a QR code) so that we could make it on our own later. I would highly recommend this class.

Small-Group Montepulciano and Pienza Day Trip from Siena

Mark_Y, Nov 2025

A great day in Tuscany!

We had a wonderful day with our amazing and awesome guide, Daniele. He was extremely knowledgeable and informative and personable. He shared bits of history and interesting facts about the area. His knowledge of wine and it’s production is impressive. He’s a true connoisseur of great wine. A little bit of a long day but worth every minute. We returned to our meeting point at about 6:15pm. I highly recommend this trip!

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

ToniAnne_S, Oct 2025

Jacopo is both knowledgeable and passionate about the history and customs of Siena

Jacopo was a very knowledgeable and friendly guide. To begin with he sent us a What’s App message with a picture of where we were meeting with the exact meeting spot circled in red. This was so helpful. As we walked between our food stops Jacopo extended on our previous knowledge of the city, bringing to life the past and present history and traditions of Siena. While I have had other wine tastings no one ever explained the ratings and classifications of wine in Italy to me as clearly as he did. His 5 choices of food stops gave us a taste and understanding of local food. We both enjoyed our meal immensely! In the Norton husband and I had a walking tour of the city and what I think was most notable about Jacopo is that rather than repeat what we learned he asked us questions and then added to our knowledge.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Mark_R, Oct 2025

Exceptional wine tasting and lunch in Tuscany!!!

My wife and I enjoyed three wine tastings in Tuscany and this was the best. The location is beautiful. The wine was great and lunch was delicious. The service was also great. I would highly recommend this particular tour and I would return in a heartbeat!

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

Erin_K, Oct 2025

Best Experience in Italy!!!

This was an AMAZING experience!! We spent all day tasting high quality wine at very small family vineyards and enjoying authentic Italian food made in their kitchens. Our guide, Mattia, was so great! He was knowledgeable (a wine-maker himself) and SO funny! Our group was small (8) and we became fast friends. We cannot recommend this tour highly enough!!

Skip the Line: Siena Duomo and City Walking Tour

Sharon_S, Oct 2025

Wonderful tour that hits many highlights of culture, history, and art.

We learned about many of the unique traditions of Sienna and its "animal" neighborhoods, along with wonderful tidbits about the cathedral and the Duomo. 2 hours was a perfect amount of time for us, and gave us a wonderful overview of the beautiful and long history of Siena and its people. Claudia is a learned and upbeat guide and a proud lifelong resident of the city. Go, Unicorns!

Hidden Castles & Chianti Wine Experience– Small Group

Jeremy_P, Oct 2025

Tour host was extremly...

Tour host was extremly knowledgeable and created a friendly atmosphere on the mini-bus. The 2 wine tasting experiences were excellent, but contrasting. One being more of a family vine yard located on an old Tuscan farm in the hills, the other being a dedicated tasting / function venue, hosted by a charismatic Sommelier. Quality of wine superb and from my hazy memory exceeded the 7 glasses advertised! Only down side was disorganised pick-up at station. Having a wine tour notice on bus and having host there at stated meet time, 15 mins before departure. Italian speaking driver turned several clients away before host arrived. Still a 5-Star tour though, as rest of afternoon made up for this.

Siena: A Wine Tour and Tasting Experience

Hannah_N, Sep 2025

Great Tuscan experience

I'm so glad I chose to book this at the last minute. La Lastra winery is stunning and picturesque, just what I pictured when I planned a visit to Tuscany. Maya was a knowledgeable and warm guide who gave us lots of engaging information about the wines and answered our questions. The homemade meal and wine tasting was a highlight. And it wasn't awkward at all going along solo.

Tuscan Cooking Class in Central Siena

Alexandra_S, Aug 2025

Incredible experience

My fiancé and l had the most incredible experience at this Tuscan cooking class. From the moment we arrived, Francesco and Giulia made us feel completely welcome. They are not only warm and kind hosts, but also so knowledgeable about the traditions and techniques behind Tuscan cuisine. Every step of the class was hands-on, fun, and full of little tips we’ll definitely take home with us. The dishes we prepared together turned out to be the best food we had during our entire stay in Siena—fresh, flavorful, and made with precision. Sharing the meal at the end with the other couple in the class felt like dining with friends rather than in a class. We left with full hearts (and full stomachs!) and cannot wait to recreate these recipes in our own kitchen. If you’re in Siena, this is an absolute must-do experience.

Siena: Small group Cooking Class in Chianti Farmhouse

Grace_C, Jul 2025

Best cooking class ever!!

Amazing experience!! Simone was an incredible host and cooking instructor. The day was fun and full of learning and enjoying! The food was delicious and the views were stunning. We took a taxi there and were nervous about getting back to Siena but Simone called a taxi for us so we didn’t even have to think about it. This experience was a highlight of our trip!

A Brunello Cooking Class with Vineyards View Winery

Jonathan_S, Jul 2025

Wonderful chef, truly fun experience

Wonderful is how I would describe this. Chef Alexandra was so engaging and made this experience exceptional. We enjoyed the classic farmhouse setting and the small group (eight) class. We definitely learned the basics and some great tips for making pasta, and had a wonderful time relaxing on the terrace enjoying our food, with wine, afterwards. I would definitely recommend this to anyone traveling to the Tuscany area.

Hot Air Balloon Flight Over Tuscany from Siena

malvarezymailcom, Jun 2025

Spectacular balloon ride over Siena- WOW!

The balloon ride was absolutely incredible! It was on my bucket list and what a perfect place to do it over Tuscany- WOW! Our operator Oliver was very knowledgeable and skilled and we felt steady and safe the entire time. The views breathtaking !! Loved the drone footage as well!- so professional. It was our 40th anniversary and truly an unforgettable experience and the highlight of our trip! The return breakfast and champagne toast was a wonderful way to celebrate it all. Perfection! So happy we decided to do this.