All Siena Tours &amp; Excursions in 2026 - page 3

Pisa Traditional Food Tour

Free Cancellation
3 hours 30 minutes

from $140

Avoid the stress of navigating winding country roads or unfamiliar public transit on your own and instead discover the fine wines and rich historical heritage of Chianti on this full-day trip from Siena. Travel through the Tuscan countryside to Castello di Brolio in the heart of the Chianti wine country for guided tasting sessions and a traditional Italian lunch. Enjoy the intimate atmosphere of a small group capped at only eight people.

Small-Group Chianti Trip with Wine Tasting from Siena

(73)

Free Cancellation
8 hours

from $223

A wine expert who will guide you through the tasting journey. Wine tasting that includes 2 Spumante and 3 Red Wines. Olive Oil tasting that includes Truffle, Chili Pepper, and Extra Virgin Olive oil. Aceto Balsamico tasting that includes Onion and Modena vinegars. Tuscan appetizers: Salame toscano, finocchiona, prosciutto crudo toscano, pecorino, bruschetta with fresh tomato and basil, cialda di pane tostato with Extra Virgin Olive Oil. First course: Penne al ragù or Penne al pomodoro. Second course: Arista with roasted potatoes. Dessert: Cantuccini and Vinsanto

Dinner with wine tasting at Poggio ai Laghi winery

(3)

Free Cancellation
2 hours

from $66

Get up close and personal with Tuscany’s ineffable scenery, and explore with ease, on a full-day tour by electric bike. Meet your guide in Siena, get familiar with your bike and helmet, and head into the Chianti Hills. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local farm/winery, where you can enjoy a traditional meal and generous wine tasting.

Small Group E-Bike Chianti Tour with farm lunch from Siena

4.8

(34)

Free Cancellation
6 hours

from $223

4.5

(291)

Skip-the-Line Siena Cathedral Duomo Complex Entrance Ticket

Free Cancellation
1 to 2 hours

from $23

Private Tour: Secret Siena Walking Tour

(108)

Free Cancellation
3 hours

from $329

Per group

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. Our location is the very framework of the 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.

Cooking class with fresh pasta, meat and tastings of 4 wines

(2)

Free Cancellation
3 hours

from $147

Explore Val d’Orcia, a UNESCO World Heritage site known for its stunning landscapes, art, and rich food traditions on this private tour. Visit Montalcino, home of the renowned Brunello wine, where you'll enjoy a guided winery tour and lunch. Then, head to Montepulciano, a medieval city with Renaissance palaces and sweeping valley views, famous for its Vino Nobile wine. Enjoy wine tastings in both towns while taking in their historical and scenic beauty.

Private Montalcino and Montepulciano Tour from Siena

(1)

Free Cancellation
7 to 8 hours

from $610

Embark on a sensory journey at Poggio ai Laghi, nestled in the heart of Tuscany, Italy. This unique tasting tour is not just about savoring the flavors of exquisite wines, oils, and vinegars, but it’s an immersive experience that engages all your senses. The tour begins with a tasting of Poggio ai Laghi wines dedicated to Donna Ava and her handmaids. Each sip tells a story of the rich Tuscan soil and the meticulous care taken in every step of the winemaking process. Next, you’ll sample the estate’s olive oils as well as the special chili pepper oil and white truffle olive oil. The tour concludes with a sampling of Poggio ai Laghi artisanal vinegars: the balsamic viegar which is an all-Italian excellence and the special vinegar with Valdelsa onions.. The wine expert will guide you through each tasting, explaining the production process, the flavor notes to look out for, and the ideal food pairings.

Chianti Grand Tasting: Signature Wines, Oils & Balsamics in the

4.8

(30)

Free Cancellation
1 hour 30 minutes

from $59

Experience the highlights of southern Tuscany on a full-day small group 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

Free Cancellation
9 hours

from $151

Immerse yourself in the culinary traditions of Siena during a small-group cooking class set in a charming historical villa. Discover the secrets of Tuscan cuisine and learn to prepare authentic Italian dishes, including ravioli and tiramisu, under the guidance of a skilled chef. After, indulge in a wine tasting, savoring the flavors of local wineries. Finally, tour the villa and admire its rustic charm and surroundings.

Cooking Class in a historical Palace in Siena Provence

4.9

(42)

Free Cancellation
3 hours

from $135

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills. In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.

Private Grape stomping in Chianti from Siena

(1)

Free Cancellation
5 hours

from $454

Experience the hospitality of Poggio ai Laghi with your loved ones, in our authentic Chianti winery. This cozy lunch, leaves you with a deeper appreciation for the art of winemaking and the beauty of the Tuscan winemaking history. Our wine expert will walk you through the tasting journey. As you learn about the winemaking process and the passion behind each bottle, the food and wine experience becomes more than a meal—it becomes a memory, and quite possibly your most cherished souvenir from the Tuscan countryside. You’ll sample a selection of our finest wines, showing the skill and dedication of our winemakers. You’ll also savor the winery’s exquisite oils and vinegars, each one crafted with the same attention to detail and quality as the wines.

The Countess’s Lunch: Wine Tasting Paired with Signature Cuisine

4.3

(16)

Free Cancellation
1 hour 45 minutes

from $82

Experience the enchantment of Siena with an enthusiastic local guide on this private tour. Discover famous sites such as Duomo di Siena, Piccolomini Library, and Piazza del Campo, while revealing secret treasures on your journey. This personalized, adjustable tour allows you to explore Siena in your style, featuring expert suggestions and captivating narratives that animate the city’s history.

Highlights & Hidden Gems of Siena Private Tour - Duomo Included

(20)

Free Cancellation
3 hours

from $228

Renting a Vespa for the day offers a truly immersive and unforgettable way to explore the heart of Chianti. Glide through picturesque Tuscan landscapes—lined with vineyards, olive groves, and golden fields—at your own pace, soaking in the sights, scents, and silence of the countryside. What sets this experience apart is the sense of freedom, intimacy with nature, and the iconic charm of riding a Vespa through postcard-perfect scenery. Easy to handle and ideal even for beginners, each Vespa comfortably seats two—perfect for couples or friends sharing the adventure. This is not just a ride; it’s an authentic slice of Tuscany, seen and felt from the seat of a classic Italian scooter.

Full Day Vespa Rental from Castellina in Chianti

Free Cancellation
8 hours

from $106

Per group

Discover the authentic beauty of Tuscany with our tour of vineyards, art and flavours. We begin with a walk through the vineyards, immersed in the heart of Chianti, to reach the charming little church of San Giorgio a Lapi, dating back to 1100. Here you can admire three splendid frescoes by Nasini, a true hidden gem. After the visit, we will enter our cellars to discover the winemaking and aging process of the wine. And to end in style, a tasting awaits you on our panoramic terrace, overlooking the Crete Senesi, accompanied by a lunch with the best typical Tuscan products, all in the shade of an ancient white mulberry tree. Live an unforgettable experience between nature, history and good wine!

Guided Tour of the Cellars with Wine Tasting and Lunch

(3)

Free Cancellation
3 hours

from $76

Combine three of Italy’s most vital delights—wine, landscapes, and history—on this tour of the 15th-century Castello Tricerchi Montalcino wine estate. Exploring in a group no larger than 15, discover 600 years of history, including the chapel, the vineyards, and the cellars. Round off your visit with a tasting of three signature wines—Brunello di Montalcino, Rosso di Montalcino, and a Toscana IGP—paired with delicious local nibbles.

Montalcino Castle and Vineyards tour with tasting

3.9

(35)

Free Cancellation
1 hour

from $46

Avoid the challenge of navigating Tuscany’s rural roads and finding hidden countryside trails on your own with a guided horseback ride from Siena. This gentle journey carries you through rolling hills, vineyards, and olive groves, reaching quiet landscapes that cars can’t access. Ride at a relaxed pace while taking in the region’s natural beauty and rural charm without any planning or navigation stress.

Tuscan Chianti Hills Horseback Riding Tour

4.0

(61)

Free Cancellation
1 hour 30 minutes

from $88

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

4.6

(8)

Free Cancellation
2 to 6 hours

from $56

Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

San Gimignano, Chianti, and Montalcino Day Trip from Siena

4.3

(150)

Free Cancellation
11 hours

from $164

Private Grape stomping at Chianti Farmhouse

4.9

(11)

Free Cancellation
4 hours

from $374

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.

Small-Group Chianti and San Gimignano Sunset Trip from Siena

4.8

(63)

Free Cancellation
8 to 9 hours

from $223

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

4.7

(7)

Free Cancellation
11 hours

from $164

This experience offers a dynamic tasting path in the heart of Siena, designed for those who want to discover wine in an engaging way, without leaving the historic center. An ideal format to combine culture, conviviality and wine pleasure in a short time. The tasting combines two different styles: bubbles and red wines, allowing participants to understand the main differences between production methods and expressions of the Tuscan territory, with clear and accessible explanations. The experience is guided by an Expert who accompanies the participants in reading the wine, helping them to recognize aromas, structure and characteristics, making the tasting suitable for both beginners and enthusiasts. The small size of the group guarantees a relaxed and interactive atmosphere, ideal for asking questions, discussing and experiencing an authentic moment linked to the local wine tradition.

Wine tasting tour in the historic center of Siena

Free Cancellation
1 hour 30 minutes

from $47

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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.

Skip the Line: Siena Duomo and City Walking Tour

Susan_A, Jan 2026

Sensational Siena!

So glad we did this tour. We were very fortunate that it was only myself and a friend so we had Georgia to ourselves! She was a fantastic guide and so knowledgeable about the history of Siena. Georgia made the tour very specilaised and answered lots of our questions. It was wonderful learning about this beautiful city from a passionate local. Highly recommended.

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!

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!!

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!

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

Sabet_S, Oct 2025

Amazing tour with Sondra!

We had such a great overview of Siena and delicious food! Sondra took us to all of her favorite spots and we had the best pasta at our lunch place! It was so good that I took a group of 10 people back a few weeks later- and she even assisted with the booking! I loved the history she shared about Siena, and it was so much more than a food tour. I highly recommend booking this tour and asking for her. I’m hosting another group in 2027 and hope to use her for a group tour once it’s all planned. Thank you!!

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.