All Siena Tours &amp; Excursions in 2026

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.

(1)

from US$106

E-Bike rental in Tuscany

1 dayFree Cancellation

4.9

(7)

from US$53

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

1 hour 30 minutesFree Cancellation

4.7

(109)

from US$70

From Siena Best of Tuscany Wines and Lunch in Montepulciano

Experience the highlights of southern Tuscany on a full-day tour from Siena through the rolling landscapes of the Val d’Orcia. Travel in comfort and enjoy a perfect blend of food, wine, history, and scenery. Your first stop is Montepulciano, where you’ll enjoy an authentic Tuscan lunch featuring local cured meats and cheeses, followed by handmade Pici pasta with ragù, or tomato sauce for vegetarian guests. During lunch, take part in a guided tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional cuisine. Continue to Pienza, the “ideal Renaissance city,” and enjoy free time to stroll its picturesque streets, admire panoramic countryside views, and browse artisan food shops. In the afternoon, reach Montalcino, home of the prestigious Brunello di Montalcino. Visit a local winery for a guided tasting and learn about the traditions and aging process behind one of Italy’s most celebrated wines.

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 hoursFree Cancellation

4.0

(5)

from US$152

If you've only got limited time in Siena, make sure you maximize your experience of the Tuscan hot spot on a sightseeing tour that includes skip-the-line entry. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo and stroll the streets with your guide, learning about the history of the place and leaving the navigating to someone else. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket.

Skip the Line: Siena Duomo and City Walking Tour

2 hoursFree Cancellation

4.8

(743)

from US$47

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 US$41

Montalcino: Brunello Wine Tasting Experience

1 hour 30 minutesFree Cancellation

4.3

(58)

from US$38

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

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.

4.7

(108)

from US$87

Likely to Sell Out

Hidden Castles & Chianti Wine Experience– Small Group

Chianti Vespa Tour

4 hoursFree Cancellation

4.7

(6)

from US$129

5 hoursFree Cancellation

4.5

(176)

from US$58

Precision and Mastery: The delicate riddling process

Explore the fascinating world of Tuscan sparkling wines with us! Book our unique experience now and discover what makes our business so special. During the guided tasting, you will be immersed in the art and science of sparkling wine production. Our wine educators will guide you through an exclusive selection of three Tuscan sparkling wines, each produced with a different production method: the classic method, the charmat method and the ancestral method. This experience will not only allow you to savor the unique flavors of these high-quality sparkling wines, but will also give you an in-depth understanding of the different techniques used in their production. You will be fascinated by the diversity of aromas and complexity that each production method adds to the wine.

Exclusive Wine Tasting in the Historic Center of Siena

1 hourFree Cancellation

Savor the fresh flavors of Sienese cuisine in this small-group morning or afternoon cookery class in Siena. Visit the home of Cesarina, your host, and roll up your sleeves for an immersive cooking experience—Sienese style. With all utensils and ingredients included, follow three traditional local recipes with helpful hints and tips from your host. Then, enjoy your food with a glass of wine among your fellow chefs.

(37)

from US$41

The Cesarina showing one of the recipe of the cooking class

Cook and Taste with a Local in Siena by Cesarine

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.

(31)

from US$41

Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

4.9

(301)

from US$224

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

11 hoursFree Cancellation

4.5

(175)

from US$93

Italian Opera in Siena Experience

1 hour 20 minutesFree Cancellation

4.8

(74)

from US$38

Siena Underground Wine tasting in a Medieval Cave

1 hourFree Cancellation

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?

(55)

from US$89

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 US$7

Price varies by group size

Siena: A Wine Tour and Tasting Experience

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.

(376)

from US$100

Chianti Half Day Wine Tasting Tour from Siena

Chianti Half Day Wine Tasting Tour from Siena

5 hoursFree Cancellation

4.4

(9)

from US$58

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

Avoid the hassle of planning routes between scattered wine towns and booking separate tastings on your own with a guided day trip from Siena. This experience connects the flavors of Montepulciano and Pienza with the scenic landscapes of Val d'Orcia, letting you move easily between villages without logistics stress. Spend your time enjoying wine, local food, and countryside views at a relaxed pace.

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

10 to 11 hoursFree Cancellation

3.9

(101)

from US$152

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

9 hoursFree Cancellation

4.9

(979)

from US$224

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

1 to 2 hoursFree Cancellation

4.5

(292)

from US$23

Siena Highlights Private Walking Tour With A Guide (Private 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.

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

Price varies by group size

4.6

(30)

from US$106

Lunch in a Tuscan vineyard with wine tasting

2 hoursFree Cancellation

Tuscan, Italian, tiramisu cooking class and tasting 3 wines

(5)

from US$85

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Top Attractions in Siena

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Attractions

What are people saying about Siena

VictoriaLynn_T, May 2026

A perfect and fun Italian experience!!

This was so fun!! My husband and I had a great time creating something new that we can now go home and try!! We created the pastas and the chefs cooked them with the sauces. The butter and sage sauce they put on the ravioli was incredible. We were so happy to do something fun and Italian haha. Our teacher was so fun and made it easy to learn. We would definitely recommend this!!

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

Rosanna_D, May 2026

Cooking in the Tuscan Countryside

It was a wonderful experience in the countryside of Tuscany. Very rustic but warm and inviting. The owner and chef Simone was outstanding, extremely friendly, included everyone. He ensure everyone was looked after ans has fun completing all the steps in preparing the food. It was a lively atmosphere with fun and laughter. We were a group of six and had an absolutely fantastic day. Highly recommended.

Small-Group Montepulciano and Pienza Day Trip from Siena

Valerie_C, May 2026

Food, wine and Tuscany. What could be better?!

My adult son and I truly enjoyed the trip, and most of the credit goes to our tour guide, Will. He was so knowledgeable, humorous and accommodating. He answered so many questions, and obviously took pride in sharing his love of Tuscany. We stopped several times to take photos, went to the small town of Pienza and enjoyed cappuccino on the flowered patio. Then onward to a local farm, and received a tour of the olive grove and grapes and the animals, and were treated to a delicious wine tasting of the farmer’s wine, as well as a lunch of varied meats and cheeses, a delicious soup-like dish of bread and beans and some almond biscotti with honey and sweet wine. Then on to Montepulciano for a wine tasting and free time to explore the town. A delightful day!

Siena: A Wine Tour and Tasting Experience

Steven_C, May 2026

Wonderful wine tour in the Tuscan hills

This was a wonderful organic vineyard and wine tasting tour in the beautiful hills of Tuscany, just outside Siena. Our host (and sommelier) was top notch - extremely knowledgeable, charming and passionate about their entire process and various wines. The light lunch and wine tasting segment of the afternoon was a perfect ending to a very enjoyable visit. Would highly recommend this tour if a vineyard and wine tasting event is on your to do list while in Tuscany.

Skip the Line: Siena Duomo and City Walking Tour

SusanJoan_S, May 2026

Good overview of Siena

Well paced walking tour with a good overview of Siena. Highlights of the key sights and history. Sylvia did a nice job of keeping the large group together. The only drawback was the low quality of the headset technology. But easy meet point with convenient parking and ends at the Duomo for access to the rest of town.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Robin_H, Apr 2026

Fabulous!!

Stunning drive to this beautiful, sun-soaked castle in Montalcino. Our hostess was so lovely and shared just the right amount of information. We enjoyed an amazing lunch paired with delicious wine—and couldn’t resist taking a couple bottles with us. Highly recommend this tour…we absolutely loved it.

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!!

Private Tour: Secret Siena Walking Tour

Jay_S, Oct 2025

Wonderful Tour, Great Guide!

Our tour guide, Giorgia, was very personable and knowledgeable. We learned a great deal about Siena and a short amount of time. A highlight was Giorgia's expertise regarding the Duomo pavement art. Truly fascinating. The pace of the tour was perfect and Giorgia walked the streets discussing it's history and views with patience.

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.

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.