All Siena Tours &amp; Excursions in 2026

Skip the Line: Siena Duomo and City Walking Tour

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.

(753)

from $46

From Siena Best of Tuscany Wines and Lunch in Montepulciano

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 hoursFree Cancellation

4.4

(9)

from $115

Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

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.

(2)

from $105

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

(115)

from $68

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.

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?

Chianti Vespa Tour

4 hoursFree Cancellation

4.1

(7)

from $127

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

4.4

(39)

from $7

Price varies by group size

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.

Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

Price varies by group size

(258)

from $180

E-Bike rental in Tuscany

1 dayFree Cancellation

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

(9)

from $52

11 hoursFree Cancellation

4.5

(177)

from $92

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.

Private Tour: Montalcino Wine Tasting Experience

8 hoursFree Cancellation

Price varies by group size

(66)

from $407

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.

Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

4.9

(316)

from $221

Horsebackriding - explore Tuscan nature

Siena: A Wine Tour and Tasting Experience

4.7

(31)

from $99

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

(385)

from $99

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.

4.6

(121)

from $86

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

9 hoursFree Cancellation

4.9

(997)

from $221

Special Offer

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

Hidden Castles & Chianti Wine Experience– Small Group

5 hoursFree Cancellation

4.5

(179)

from $57

Tuscan Chianti Hills Horseback Riding Tour

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

1 hour 30 minutesFree Cancellation

4.0

(61)

from $87

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.

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

2 hours 30 minutesFree Cancellation

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.

(19)

from $69

Likely to Sell Out

San Gimignano, Chianti, and Montalcino Day Trip from Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena

11 hoursFree Cancellation

4.3

(151)

from $163

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan with an English-speaking driver and complimentary water. Small group experience, maximum 8 participants. Please note that from November to April, and in case of bad weather, lunch will take place indoors. For tours departing on Mondays, lunch is always served in an indoor restaurant. Why choose us? • Guaranteed departures • Secure booking • 24-hour cancellation policy • Best rates guaranteed For operational reasons, the itinerary order may vary between Montepulciano and Montalcino.

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

4.6

(5)

from $266

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

(44)

from $41

Special Offer

Chianti and Castles Tour from Siena Small Group

Discover the picturesque wine region of Chianti on a half-day excursion from Siena. Enjoy the Tuscan scenery of gently undulating hills and vineyards while tasting Chianti wines. A day journey from Siena to the Chianti region allows you to experience the gorgeous Tuscan landscape. Begin with a visit to Castellina in Chianti, followed by a wine tasting at a nearby vineyard. Immerse yourself in the bright colors of the rolling hills, where the views, smells, and flavors of the region will captivate your senses. Enjoy a stroll in Monteriggioni, a medieval village where time seems to stop. Proceed to another winery in the heart of the Chianti Classico region, where you can have a second wine tasting and sample extra virgin olive oil. A return trip to Siena marks the end of the excursion.

Chianti and Castles Tour from Siena Small Group

5 hoursFree 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.

Cook and Taste with a Local in Siena by Cesarine

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

(33)

from $41

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Top Attractions in Siena

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The magnificent Gothic and Romanesque structure of Siena Cathedral (Duomo).

Attractions

What are people saying about Siena

Alisha_F, Jun 2026

Book It Now!

This tour was awesome! We traveled with friends (two couples) and the tour was us and one other person who became a fast friend! Our guide Jacapo was wonderful! He was local and knew all about local history and traditions. The food and wine was plentiful! In addition, the tour included lots of educational pieces about the food and wine of Siena! He also sent photos and other recommendations the next morning. Don’t hesitate to book this-so good! Great way to see and taste the history of Siena!

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

Jennifer_B, Jun 2026

Traditional Tuscan Treat

This was the best cooking class I have experienced - based on other experiences in France, China, and the United States. Francesco, who is now the owner, and Julie , who also helped translate from Italian to English, both gave each of us (7 participants) individual attention on techniques, tips along the way, and patiently answered questions in between demonstrations. The food we created from all fresh and local ingredients was delicious and based on traditional local Tuscan cuisine! When any friends and family visit Siena, I will be recommending this experience! And for the reader here, you will enjoy every step of the process!

Small-Group Montepulciano and Pienza Day Trip from Siena

Jennifer_H, Jun 2026

Our time in Montepulciano...

Our time in Montepulciano was one of our favorite days in Italy. Giovanni was an exceptional guide and he taught us so much about the wine and the area. We highly recommend Tuscan Wine Tours as they book small wineries. Our delicious lunch was at a dairy farm where we overlooked the gorgeous Tuscan region.

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

lisa_s, Jun 2026

Great family fun in Siena

This was such a fun experience! Our instructor was amazing, personable and knowledgeable and we learned some great tips and techniques. The cooking space was light, bright and wonderful. It was so fun to eat our pasta and tiramisu at dinner afterwards. Our family of 7 adults had a great time. We highly recommend this class!

Skip the Line: Siena Duomo and City Walking Tour

Kevan_A, Jun 2026

Siena Duomo and walking tour

A very enjoyable two hours spent walking through Siena and the Duomo. Elio, our guide had an extensive knowledge of the history of Siena, its customs and people. With his wonderful sense of humour he kept all of us entertained with his stories. The Duomo was very busy and partially closed due to Republic Day but we were able to see and hear enough about this magnificent building to make the tour very worthwhile.

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

Donna_N, May 2026

Must do tour!

Absolutely amazing experience in the Tuscan countryside. Our tour guide Paulo was so much fun and so knowledgeable of the area and the history of Siena and the region. All three wineries offered fantastic tasting experiences and were so welcoming. Lunch with the wine maker at his home was a highlight. This tour is an absolute must!

Tuscan, Italian, tiramisu cooking class and tasting 3 wines

Karen_G, May 2026

Fun and informative cooking class!

We gathered for a glass of prosecco and introductions to start. First we learned how to make and assemble tiramisu - simple yet precise. Then we made and kneaded pasta dough. We stretched the dough through a pasta machine then made 3 shapes - ravioli, tortellone, and tagliatelle. Our instructor, Joanna, was fun, energetic and positive. She gave great tips throughout and praised us, even when our shapes didn't turn out quite right. 😄 We enjoyed a hearty lunch of each pasta with a complimentary sauce. The wine tasting option was great, as we tasted new varieties of wines that paired well with the pastas. Overall an excellent experience - highly recommend!

Siena: A Wine Tour and Tasting Experience

Joseph_M, May 2026

A wonderful wine experience

Cristian was a fantastic host/guide! He was very knowledgeable about the wine growing, harvesting, and distillation processes. There was a great assortment of wines, perfectly paired with food & dessert. He and the staff also helped with getting taxis back to Siena train station, which was very kind and helpful. It was a great way to spend the day in Siena, have great food, and learn about wine.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Desmond_R, May 2026

Awesome experience

It is a small bit of everything you'd want to experience at a vineyard ☺️. The guide and her team are friendly, helpful and happy that you are their guests. We enjoyed the small tour of history and the 3-course meal was a light delight. The wines were delicious 😋. Lovely experience for the price at hand.👌🏾

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!!

Hot Air Balloon Flight Over Tuscany from Siena

Marita_L, Oct 2025

Absolutely an experience not to miss

They do a great job in making sure that the flight will be safe, gauging the weather and letting you know if it has to be canceled or moved to a new location. While a new location can be inconvenient it is for your safety. I appreciate the care they take. The experience was extraordinary. The staff was very helpful and they treat you with kindness and respect.

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.