All Siena Tours &amp; Excursions in 2026

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 hoursFree Cancellation

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.

(1)

from $142

Skip the Line: Siena Duomo and City Walking Tour

2 hoursFree Cancellation

(727)

from $48

E-Bike rental in Tuscany

1 dayFree Cancellation

Hidden Castles & Chianti Wine Experience– Small Group

(7)

from $54

5 hoursFree Cancellation

4.5

(175)

from $59

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.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

1 hour 30 minutesFree Cancellation

4.6

(104)

from $70

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

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.

(972)

from $227

Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

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

(293)

from $227

11 hoursFree Cancellation

4.5

(173)

from $94

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.

Chianti Vespa Tour

4 hoursFree Cancellation

Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

(5)

from $130

2 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?

(1)

from $84

Siena Walking Tour with Audio and Written Guide by a local

4 to 5 hoursFree Cancellation

4.3

(35)

from $7

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

5 hoursFree 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.

(7)

from $59

Hot Air Balloon Flight Over Tuscany from Siena

3 hoursFree Cancellation

(137)

from $371

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience. Begin your full-day journey by seeing San Gimignano, well known as the City of Fine Towers. With your tour guide's insights, take advantage of your free time to explore the historical center and its artisan stores. Explore the birthplace of Vernaccia, the renowned white wine that is regarded as Italy's first DOCG wine, after that. Enjoy a sample of Chianti and you can choose to buy the optional lunch at a nearby winery. Discover the UNESCO World Heritage Site of Val d'Orcia before continuing on to Montalcino, which is famous for its panoramic vistas of Brunello grapes. Finish your tour by visiting a local wine cellar to experience the renowned Brunello di Montalcino.

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

11 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.

(8)

from $167

Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

(254)

from $185

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

2 hours 30 minutesFree Cancellation

Italian Opera in Siena Experience

(64)

from $90

1 hour 20 minutesFree Cancellation

DEPARTURE GUARANTEED! Enjoy a perfect day trip visiting 3 of the most impressive places in Tuscany. Montalcino, house of "Brunello" wine; Pienza, well known for the "Pecorino" cheese and Montepulciano where the undisputed symbol is the "Nobile di Montepulciano" wine! Please note that from November to April I cannot guarantee the restaurant with view, as stated in the inclusions. The Valdorcia has been recognized as UNESCO world heritage site since 2004, as it was an inspiration for many Renaissance painters. There you will be surrounded by impressive views, art, culture, amazing wine and delicious food! Your semi private tour will be on board of a premium minivan with an English speaking driver, air conditioning and free water. WHY CHOOSE ME? Secure bookings, Guaranted Departures! 48 hours Cancellation policy, best rates guaranteed! Group of maximum 8 people.

(72)

from $38

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

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.

(1)

from $274

Siena : Siena Guided Tour with Duomo or Museum

1 hourFree Cancellation

4.3

(43)

from $42

Siena Underground Wine tasting in a Medieval Cave

1 hour 15 minutesFree Cancellation

With no train station and spotty bus service, San Gimignano can be a hassle to reach from Siena. On this small-group tour, sip world-class wine and watch the sunset over Chianti and San Gimignano with stress-free transportation. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills.

(52)

from $90

Small-Group Chianti and San Gimignano Sunset Trip from Siena

8 to 9 hoursFree Cancellation

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.

(63)

from $227

Likely to Sell Out

Siena Private Highlights and Hidden Gems Walking Tour

2 to 6 hoursFree Cancellation

(4)

from $91

Discover UNESCO-listed Siena through the eyes of a local on this custom-made Lokafy walking tour. Skip the typical guided tour and instead connect with a Siena local who will show you around their city like a friend and introduce you to the neighborhoods that they know and love. As you explore the city, gain an insight into Tuscan culture, cuisine, and everyday life; and receive recommendations on where to eat, drink, and shop.

Siena Private Walking Tour with a Local

2 to 6 hoursFree Cancellation

4.4

(11)

from $57

Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.

Tuscan Cooking Class in Central Siena

4 hoursFree Cancellation

Tuscan, Italian, tiramisu cooking class and tasting 3 wines

(344)

from $155

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Top Attractions in Siena

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Attractions

What are people saying about Siena

Sue_H, May 2026

Great night out!

It’s an authentic family trattoria and the chefs running the classes make them fun and interesting. The classes are in a purpose built cookery school and then you move next door to the restaurant to eat your own food. Add in the wine tasting too for the full Italian experience. Ayoub, our chef, was just great!

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

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.

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.

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!

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.

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.

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.