THE TOP 20 Siena Likely To Sell Out (UPDATED 2026)

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

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.

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San Gimignano, Chianti and Montalcino Tour through Tuscan wine

11 hoursFree Cancellation

4.8

(8)

from $165

Likely to Sell Out

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

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.

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

3 hoursFree Cancellation

4.9

(234)

from $86

Likely to Sell Out

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

4 hoursFree Cancellation

4.8

(176)

from $135

Likely to Sell Out

Cooking Class in a historical Palace in Siena Provence

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.

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Cooking Class in a historical Palace in Siena Provence

3 hoursFree Cancellation

4.9

(43)

from $138

Siena walking tour with lunch & Chianti wine

Take a tour of Siena with a local, and get the lowdown on the city that the guidebooks can’t give. In a small group, explore Siena by foot to discover the history behind the UNESCO-listed Piazza del Campo, the oldest bank in the world, and other monuments. You also have a chance to sample classic food and drinks from Tuscany such as Pecorino cheese, homemade pasta known as pici, the famous Chianti wine, and more.

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Siena walking tour with lunch & Chianti wine

2 hours 30 minutesFree Cancellation

4.8

(101)

from $100

Likely to Sell Out

Tuscany Hiking Tour from Siena Including Wine Tasting

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.

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Tuscany Hiking Tour from Siena Including Wine Tasting

4 hoursFree Cancellation

4.9

(122)

from $71

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.

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Cook and Taste with a Local in Siena by Cesarine

3 hoursFree Cancellation

4.9

(34)

from $199

Cesarine: Small group Pasta and Tiramisu class in Siena

Connect with a local cook and learn how to make two staples of classic Italian cuisine with this cooking class hosted in a local's kitchen. Discover the secrets to turning out flawless fresh pasta with two different recipes for both a stuffed and a shaped version. Then assemble a show-stopping tiramisù from scratch under the guidance of your instructor and host. Cap off your experience by sampling your creations.

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Cesarine: Small group Pasta and Tiramisu class in Siena

3 hoursFree Cancellation

4.9

(22)

from $211

Likely to Sell Out

Visit San Gimignano and Volterra the easy way from Siena, on an intimate small-grop tour. Head to the hilltop town of Monteriggioni, then stop for a while in UNESCO World Heritage–listed San Gimignano, with its medieval towers and views over the Tuscan countryside. Drop into an alabaster workshop in Volterra, then indulge in a rustic lunch at a Tuscan farm. Learn about local history and culture along the way.

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Small-Group San Gimignano and Volterra Day Trip from Siena

8 hoursFree Cancellation

4.9

(199)

from $224

Chianti Horseback Riding Tour at San Gimignano

Begin your adventure with a friendly introduction by professional staff who ensure you feel comfortable and confident before setting off. Once in the saddle, ride through lush vineyards, olive groves, native woodlands, and scenic hills, soaking in breathtaking panoramic views that define the Tuscan landscape. Enjoy a relaxing and immersive journey far from the crowds, surrounded by nature, tradition, and timeless beauty. This Chianti horseback riding experience is the perfect way to explore Tuscany at a slow pace and create unforgettable memories in the countryside.

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Chianti Horseback Riding Tour at San Gimignano

1 hour 30 minutesFree Cancellation

4.0

from $100

Siena Sightseeing Walking Tour with Food Tastings for Small Groups or Private

2 hours 30 minutesFree Cancellation

5.0

(16)

from $141

Price varies by group size

Likely to Sell Out

Pasta and Tiramisu Cooking Class in Tuscany near Siena

Immerse yourself in Italian culinary traditions with a hands-on pasta and tiramisu cooking class. Learn how to roll fresh pasta ('sfoglia') by hand and prepare two iconic pasta dishes from scratch. Plus, master the art of making Italy’s beloved dessert, tiramisu. Join a small group and share your love for Italian cuisine while connecting with fellow food enthusiasts. The experience begins with an Italian Aperitivo to kickstart your cooking adventure. Hosted by Cesarine, Italy's oldest network of home cooks, this class offers a unique opportunity to learn from passionate local hosts who share authentic regional specialties passed down through generations. A perfect way to experience the heart of Italian culture!

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Pasta and Tiramisu Cooking Class in Tuscany near Siena

3 hoursFree Cancellation

5.0

(2)

from $159

Likely to Sell Out

Florence Duomo Cathedral Guided Tour from Siena

7 hours 40 minutesFree Cancellation

4.0

from $87

Likely to Sell Out

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.

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Chianti Vespa Tour

4 hoursFree Cancellation

4.1

(10)

from $128

Likely to Sell Out

San Gimignano, Chianti, and Montalcino Day Trip from Siena

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.

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San Gimignano, Chianti, and Montalcino Day Trip from Siena

11 hoursFree Cancellation

4.3

(151)

from $165

Likely to Sell Out

Siena Bites & Stories: A Tasty City Adventure with a Local

To fully discover a city one may participate in a lot of tours and go eat at many venues published on travel guides and recommended by online travellers but the true local knows where to take you and you'll be paired with a Local Expert who will tell you stories, curiosities and will take you to spots outside of the tourist lens. We'll visit the most important and the least acknowledged hitspots of the Medieval Centre of Siena. Also, with us, you'll be able to eat some of the most typical snacks available in the city and taste the local Tuscan Wines, which mean a lot to the gastronomic history of the locals. The activity is suitable to people of all ages, from the kid discovering the curiosities behing the walls of the centre to the adults learning about Siena's culture.

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Siena Bites & Stories: A Tasty City Adventure with a Local

2 hours 30 minutesFree Cancellation

4.8

(19)

from $69

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.

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Small-Group Chianti and San Gimignano Sunset Trip from Siena

8 to 9 hoursFree Cancellation

4.8

(64)

from $224

Likely to Sell Out

VIP Chianti, Brunello wine & Pienza with lunch From Siena

8 to 9 hoursFree Cancellation

5.0

(28)

from $277

Likely to Sell Out

From Siena: Pisa and San Gimignano Day Trip

Spend a memorable day exploring Tuscany’s most famous landmarks and landscapes on a relaxed and well-balanced itinerary from Siena. Your journey begins with a comfortable transfer by air-conditioned coach through the rolling hills of the Tuscan countryside. Reach Pisa, where you will have free time to explore the stunning Piazza dei Miracoli, a UNESCO World Heritage Site. Admire the world-famous Leaning Tower, the Cathedral, and the Baptistery from the outside, and take your time capturing unforgettable photos. Continue your experience with a stop in the heart of Chianti, where you will enjoy a traditional Tuscan lunch paired with a guided wine tasting at a local winery. In the afternoon, arrive in San Gimignano, one of Tuscany’s best-preserved medieval towns. On the way back from Pisa, you’ll pass through Florence before returning to Siena. This allows for a smooth and well-organized route across Tuscany.

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From Siena: Pisa and San Gimignano Day Trip

8 hoursFree Cancellation

4.0

(1)

from $93

Cesarine: Typical Dining & Cooking Demo at Local's Home in Siena

2 hours 30 minutesFree Cancellation

5.0

(8)

from $152

Likely to Sell Out

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!

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Pisa Traditional Food Tour

3 hours 30 minutesFree Cancellation

from $140

Likely to Sell Out

Explore Siena Market & Cook at a Local’s Home by Cesarine

4 hours 30 minutesFree Cancellation

5.0

(5)

from $211

Likely to Sell Out

From Siena Brunello di Montalcino Wine Tour with Lunch

Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through our organic vineyard and take in the stunning views while savoring two distinct wines alongside a delicious three-course meal. Admire the picturesque Tuscan landscape as you learn about the traditional methods and techniques used to produce our high-quality wines. The lunch menu features a selection of cured meats and cheeses, handmade pasta with flavorful sauces, and delightful desserts. A vegetarian option is available; please let us know at the time of booking if you would like this alternative.

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From Siena Brunello di Montalcino Wine Tour with Lunch

4 hoursFree Cancellation

5.0

(1)

from $164

Likely to Sell Out

Explore the enchanting streets of Siena in a unique way through a walking riddle hunt. This interactive adventure invites participants to uncover the city's fascinating stories and hidden gems at their own pace. Wander through iconic spots like Piazza del Campo while solving puzzles and challenges that reveal the rich history of this UNESCO World Heritage Site. With professional guides available for hints, this treasure hunt-style experience is perfect for families, friends, and curious travelers looking to engage with Siena's culture in a fun and dynamic way.

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Ultimate Walking Riddle Hunt in Siena

2 hoursFree Cancellation

4.0

from $71

Top Siena Likely To Sell Out

38 results

Top Attractions in Siena

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni

Siena Cathedral (Duomo di Siena)

Piazza del Campo

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni

Siena Cathedral (Duomo di Siena)

Piazza del Campo

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni