All Siena Tours &amp; Excursions in 2026

Skip the Line: Siena Duomo and City Walking Tour

2 hoursFree Cancellation

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.

(733)

from $47

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

1 hour 30 minutesFree Cancellation

4.6

(108)

from $70

E-Bike rental in Tuscany

1 dayFree Cancellation

Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

(7)

from $53

2 hoursFree Cancellation

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.

(1)

from $107

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 hoursFree Cancellation

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

(1)

from $153

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.

4.7

(101)

from $88

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

9 hoursFree 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?

(976)

from $225

Siena Walking Tour with Audio and Written Guide by a local

4 to 5 hoursFree Cancellation

4.3

(37)

from $7

Hidden Castles & Chianti Wine Experience– Small Group

5 hoursFree Cancellation

4.5

(175)

from $58

Siena: A Wine Tour and Tasting Experience

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.

(375)

from $101

Likely to Sell Out

Chianti Vespa Tour

4 hoursFree Cancellation

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

(5)

from $129

Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

(255)

from $184

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

11 hoursFree Cancellation

4.5

(175)

from $94

The Cesarina showing one of the recipe of the cooking class

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.

Cook and Taste with a Local in Siena by Cesarine

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.

(30)

from $41

Siena Private Highlights and Hidden Gems Walking Tour

2 to 6 hoursFree Cancellation

(5)

from $90

Italian Opera in Siena Experience

1 hour 20 minutesFree Cancellation

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.

(73)

from $38

Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

Montalcino: Brunello Wine Tasting Experience

(297)

from $225

1 hour 30 minutesFree Cancellation

4.3

(58)

from $38

Siena Underground Wine tasting in a Medieval Cave

1 hour 15 minutesFree Cancellation

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.

(55)

from $89

Hot Air Balloon Flight Over Tuscany from Siena

(137)

from $367

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

Likely to Sell Out

4 hoursFree Cancellation

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.

(167)

from $136

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

There are places you visit, and others you truly experience. Here, among the hills of Chianti and the Crete Senesi, the experience unfolds slowly on our terrace overlooking the landscape, under the shade of an ancient white mulberry tree. This is not just a tasting: it is a moment to share, guided by those who produce the wine every day, in an atmosphere that is genuine and never staged. The wines tell the story of the land, the food accompanies them, and everything around you comes together to create something that stays with you. If you are looking for a real experience, made of details, hospitality, and time dedicated to you, this is the right place.

(217)

from $86

Classic Wine Tasting with Traditional Tuscan Products

1 hourFree Cancellation

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.

(77)

from $33

Guided Winery Tour and Wine Tasting in Siena

2 hours 30 minutesFree Cancellation

Small-Group Montepulciano and Pienza Day Trip from Siena

(64)

from $89

1 2 3

...

Top Attractions in Siena

1 / 2

Attractions

What are people saying about 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.

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

Lynda_R, May 2026

Fun and yummy

Really fun experience, chef was engaging and funny. Made 3 different pastas and tiramisu. Once finished they take you next door to the restaurant to cook up the pasta and serve you. There was a glass of prosecco on arrival and plenty of red wine with lunch! Highly recommend

Skip the Line: Siena Duomo and City Walking Tour

Dasha_C, May 2026

This is a must-do in...

This is a must-do in Siena. Georgia was an amazing guide who packed so much information into the two hours while keeping things lively and interesting. We were there on a national holiday so the city was very busy yet she navigated our large group around the city easily.

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

James_E, Apr 2026

A Must-Do Brunello di Montalcino Wine Tour

Oh boy, where do I start? This has to be one of the best tours my wife and I have ever been on. We love Brunello wine and were really eager to tour the region of Montalcino and sample the wines at a few different vineyards. The tour was about eight hours long starting from our meeting point in Siena. We had five others on the tour with us and we fit comfortably in the van driven by our host and guide, Francesco (Kekko). Francesco grew up in the area around Montalcino and was very knowledgeable regarding the area's past, it's unique geography, and about the wine-making process itself. His English was awesome and he seemed to be able to talk non-stop, but in a good way! We visited three very different wineries and had excellent presentations by the local hosts. We also made a couple of other interesting stops including one at the walled, hilltop city of Montalcino and another at an medieval Abbey that was on the way to one of the wineries. We sampled a nice variety of wines and enjoyed the company of the other guests. The whole day really flew by. Francesco was an excellent driver, even on the many gravel roads and twisting highways, and the whole trip was very comfortable. Francesco's personal stories and his explanations of some of the cultural rituals were fun to hear. We would definitely recommend this tour and Francesco as a tour guide!

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

David_S, Apr 2026

Beautiful historic winery

A little difficult to find the winery. Make sure you specify English tour. We did not and so we had the tour in English withe the owner. He was GREAT!! We got to visit areas of the winery that not included in the regular tours. A fascinating history and the owner was is descendent of the founders and is only there part time as he is a lawyer in Rome.

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!!

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.

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.

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

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.