All Siena Tours &amp; Excursions in 2026

Fresh Pasta & Authentic Italian Sauces

Home to medieval hilltop towns and fertile vineyards, Tuscany is widely considered the jewel in Italy’s crown. On this tour, visit the beautiful Tuscan towns of Pienza and Montepulciano, and enjoy a complete immersion in authentic Italian culture and cuisine. With travel from your Chianti or Siena hotel, sample local wines in historic cellars and savor a delicious lunch in a traditional Montepulciano winery.

Cities, Cheese and Wine Tour in Pienza & Montepulciano

6 to 8 hoursFree Cancellation

Our dynamic team of cooks, tutors and interpreters will guide our guests on a voyage of discovery of traditional cooking, preparing the most typical of the local dishes, home made pasta with sauces of organic seasonal vegetables from our kitchen garden, melt in the mouth home made gnocchi, bruschetta, second courses like Vin Santo chicken or eggplant parmigiana, delicious desserts.. .all accompanied by our own Chianti Colli Senesi wine. The courses are organized for small groups (2 to 14 pax) and make the most, both our own produce, wine, honey, saffron, extra virgin olive oil, our fresh garden vegetables and also other local produce from neighboring farms. The classes start in the morning at 10.30 ending with a delicious lunch or in the afternoon around 15:30 ending with a wonderful dinner, to celebrate the joy of cooking with all the delicious dishes we have prepared together.

Cooking classes in Tuscany

4 hoursFree Cancellation

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

8 hoursFree Cancellation

Siena Award Winning Chef Pasta and Iconic Dessert Class

2 hours 30 minutesFree Cancellation

5% savings

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$79$75

Tour by Van to the Saturnia and Pitigliano Mill Falls

2 hours 30 minutesFree Cancellation

Explore Siena’s historical highlights and iconic cathedral on a private walking tour of the historic center. This short but comprehensive tour is designed for curious travelers who want to maximize their limited time in this Tuscan city. As you admire Piazza San Domenico, Torre del Mangia, and other local treasures, your guide will provide illuminating commentary that takes you out of the guidebook and into medieval Tuscany.

Siena Private Walking Tour: Traditions, Streets & Cathedral

2 to 3 hoursFree Cancellation

Discover the island of Siena at your own pace with this guided tour. With a tour of more than 2 hours, you can explore Siena discovering monuments such as Piazza Tolomei, Via Citta or the Duomo of the city. This option without schedules or groups allows you to enjoy the city flexibly, including recommendations on gastronomy and family activities. Available in six languages, this experience is ideal for those looking for hassle-free personalized tourism. - 2h self-guided tour with + 15 points of interest - Access to information in 6 languages: Spanish, English, Portuguese, French, Italian and German Explore iconic attractions and receive food recommendations. - No groups or schedules, ideal for traveling at your own pace.

TOP Siena : Private Guided Tour with your mobile

TOP Siena : Private Guided Tour with your mobile

2 to 3 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

Take a break from sightseeing and head to the Tuscan countryside surrounding Siena to join a local forager on a truffle hunt through the woods. Follow your host and his pups across the hills as they search out precious tubers and learn all there is to know about truffles and the dogs trained to hunt them. Afterwards, head back to Siena to sample a number of truffle products in a local gourmet shop.

Truffle Hunting Experience Siena Tartufi

2 hoursFree Cancellation

Discover the tricks to making authentic homemade Italian pasta and tiramisu during a private cooking class in Siena. Set in a local home, your party will enjoy the undivided attention of your friendly and experienced host. After preparing two traditional types of noodles and the famous espresso-infused dessert - using some Italian family secrets - enjoy all three with a selection of local wines.

Cesarine: Pasta & Tiramisu Class at a Local's Home in Siena

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

Take a chance to discover Siena, a jewel of the Middle Ages set in the Tuscan hills, full of history and culture. Accompanied by a specialized guide of the city you’ll walk through the characteristic streets of Siena, admiring the beauty and the magnificent of Piazza del Campo where twice a year the horses run for the Palio race. You will learn about the world's oldest bank and the pilgrim's path as you discover the secrets of the famous 17 Contrade. The historic center is a UNESCO heritage site: the Cattedrale dell’Assunta is a gothic architectural work of art that will leave you breathless. You'll be amazed by the Duomo and by the heavy chimes of the Torre del Mangia that resound throughout Siena in its most important moments, especially during the Palio. Let’s discover together the myths, legends and secrets of this medieval town!

Private Siena walking tour

Skip the crowds and delays of the train and opt for this stress-free private transfer directly from your Siena hotel to your final destination in Florence. Avoid the hassle of lugging your heavy bags and relax on board a quiet, air-conditioned vehicle while you enjoy the Tuscan views along the drive. Arrange drop-off at any location in Florence, including the airport, train station, or any city hotel.

Private transfer from Siena to Florence

1 to 2 hoursFree Cancellation

Opt for a personalized experience of Siena’s top attraction on a private tour of Siena Cathedral. With just your private guide and party, discover easy-to-miss details in the cathedral’s interior and benefit from commentary integral to understanding the statues of Michelangelo and the art inside the Chapel of St. John the Baptist. Plus, booking in advance means you save hours of waiting in line with a skip-the-line admission ticket.

Private Tour of Siena Cathedral

2 hoursFree Cancellation

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

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

6 hoursFree 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.

Small-Group Chianti and San Gimignano Sunset Trip from Siena

8 to 9 hoursFree Cancellation

Explore the enchanting Chianti region during your trip from Siena to Florence with our expert local driver, aboard a comfortable Minivan with a large trunk. Immerse yourself in the picturesque Tuscan landscape adorned with rolling hills, vineyards, cypresses, olive trees, and sunflowers. Itinerary: • Private collection at the indicated address. • 1st stop at the Monteriggioni Castle, an invincible castle and ancient outpost built by the Republic of Siena, serving as a strategic control point along the historic Via Francigena (the medieval road once traveled by Crusader soldiers and pilgrims). • 2nd stop in San Gimignano, a true open-air museum, famous worldwide for its valuable medieval towers and typical shops managed by expert craftsmen. If you wish, you can ask our driver to make an additional stop in the cellar to enjoy a typical lunch or a fine wine tasting, with an additional cost based on the extended time. This is our beautiful Tuscany for you !

PRIVATE TRANSFER from Siena to Florence with stop in S Gimignano & Monteriggioni

4 hoursFree Cancellation

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition to it, this tour has an Arts footprint. We'll lead you through some hidden sculptures, located throughout the landscape, as a warm up to our stop at the Chianti Sculpture Park, where you'll visit some contemporary sculptures and installations. We'll build on to the arts experience by stopping at the hamlet of Scopeto, where the film "Letters to Juliet" has been shot. Least, but not last, it will be wine time right after at the Scopeto Winery, where you can further develop your reconnaissance of the territory by tasting one of its maximum expression: the Chianti Classico. We then, climb back to our comfortable ebikes to return to Siena

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

5 hours 20 minutesFree Cancellation

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

Private Grape stomping in Chianti from Siena

5 hoursFree Cancellation

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

4 hours 30 minutesFree Cancellation

Pienza and Montalcino are top foodie destinations, but getting there by train and bus can eat hours out of your day. Experience the area's top cheese and wine with ease on this private tour from Siena. Admire the Val d’Orcia scenery, learn about cheese making during an organic dairy farm tour, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine at a Montalcino winery.

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

8 hoursFree Cancellation

The hot air balloon tour is a magical experience, a true adventure carried out in total safety by flight professionals. Our pilots, all with great experience, are ENAC certified commercial pilots. They will guide you during your trip, sharing with you detailed information about hot air balloons and satisfying all your curiosities about the flight and its navigation. Don't wait any longer, immerse yourself in this extraordinary adventure.

Hot air balloon over the hills of Pienza, Montalcino and Val D'Orcia

The city of the Palio runs on rivalry — ideal conditions for a scavenger hunt. This app-led scavenger hunt takes you through Siena on foot, using phone-based riddles to guide you from one landmark to the next. No guide, no fixed start time. • Decode the marble stories of the Battistero di San Giovanni • Sweep into Piazza del Campo, the shell-shaped stage of the Palio • Stand before the striped magnificence of Siena's Duomo Available in 24 languages including English, French, German, Spanish, Italian — see the full list when booking and choose yours when you start the game in the app. Around 2 hours - any group size. Seventeen contrade, one leaderboard.

Siena Self-Guided City Walking Tour & Scavenger Hunt

2 hoursFree Cancellation

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Must-Dos in Siena

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

What are people saying about Siena

Small-Group San Gimignano and Volterra Day Trip from Siena

Israel_K, Oct 2026

An exceptional day in Tuscany

A truly wonderful experience and one of the highlights of our trip to Tuscany! Our guide, Giovanni, was exceptional: knowledgeable, patient, friendly, and attentive throughout the day. His understanding of the region, its history, and its wines made the visits to San Gimignano, Volterra, and the surrounding countryside especially enjoyable. The tour felt relaxed and personal. The lunch at Il Palagione was particularly memorable. We enjoyed excellent wines, delicious home-prepared food, and the warm hospitality of the family members we met. It was a very special experience. Beautiful scenery, fascinating places, outstanding food and wine, and a fantastic guide. Highly recommended!

Small-Group Montepulciano and Pienza Day Trip from Siena

Bradley_R, Oct 2026

Extreme fun in Tuscany

Leonardo was a FANTASTIC tour guide. He was extremely personable and knowledgeable. He was very considerate of each of our tour group members wants and needs. The wine was great, the food was great and the camaraderie was even better. We had a wonderful experience and I would highly recommend it!

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

Paula_G, Oct 2026

Great value tour …highly recommended.

A great day seeing the medieval cities .. and a delicious lunch at the winery with plenty of wine to taste and enjoy. Well organised and plenty of time at each place. More walking than I envisaged, as buses have to park outside the city centres, so be prepared for this. Our guides Ricky and Christina were great…and very helpful to me when I had to take it a little slower due to a recent injury during my travels. Great value for money.

Montalcino: Brunello Wine Tasting & Tuscan Lunch

Vlada_T, Oct 2026

Brunello lover’s paradise

Expertly led wine tasting, exquisite wines, and an excellent lunch. They are passionate about the wine they make on this small vineyard and eager to share their knowledge. We sampled an array of wines, and experienced their differences. The food was homemade and top shelf. Hard to imagine a better way to spend an afternoon in Tuscany. All the other reviews are spot on. It was a thoroughly enjoyable off the beaten path experience.

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Craig_S, Sep 2026

Wine tasting in Siena

What an incredible day and a beautiful setting for a wine tour outside of Siena. We only thought we were getting a tour of the winery and some wine tasting but an incredible 4 course meal was included in the fee four our tasting and it couldn't have been more spectacular. Everyone was incredibly nice, especially Bene who was our guide for the day as we discovered the history of the winery and its origins. The wine was fantastic and we were able to also ship wine back to the United States for a nominal fee which was an added bonus. And the chef for the winery was fantastico!! Thank you again for an incredible day that was one of the biggest highlights of our trip so far, and only 15 minutes outside of Siena. Grazie Mille!!

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

Jennifer_V, Sep 2026

More than wine tour

This was an exceptional tour. Leonardo was so wonderful as our tour guide. He did a great job of educating us on the history of the growing region of Montaclino and the surrounding Tuscany region. The tour definitely exceeded our expectations. We saw 3 different wineries, toured a church and got to climb atop a very cool castle. Such a great experience we will never forget. Thank you again!

Skip the Line: Siena Duomo and City Walking Tour

Kathy_T, Sep 2026

Wonderful tour of the Duomo

Our group was about 30. Claudia, our guide was easy to understand and answered lots of questions. Enjoyed thoroughly - especially the Duomo and the floors on display. They are viewable now - usually covered. Incredible pieces of art - on the floor. Our tour ended in the Duomo and then you can spend more time exploring inside.

Siena Pasta & Tiramisu Cooking Class With Wine by Cooking Italy

Christine_G, Sep 2026

Amazing Pasta Experience, Yum

We had an absolutely wonderful time with our chef and the rest of our group! The location was impeccable, and the course was very well organized and paced. Learning how to make pasta was such a lovely experience, and the hands-on approach made it even more enjoyable. I’m thrilled to say that I can now make fresh pasta for my family and friends! Ending the day with a delicious feast made the experience even more special. I’m so glad I attended this class—it was the perfect way to complete my trip!

Siena: A Wine Tour and Tasting Experience

Kim_P, Sep 2026

Amazing experience

We had such a wonderful experience at La Lastra Winery in Siena! Lorenzo was welcoming, knowledgeable and passionate about the wines and the winery. He made our entire experience fun, relaxed and informative. We had excellent wines and food! The setting is beautiful, the wines were excellent, and pared well with what we ate. We would highly recommend this tour.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Joseph_S, Sep 2026

Wonderful Tuscan Lunch

This was an amazing experience. Way more than I had expected. We started with a tour of the property, lead by a very knowledgeable young lady (name escapes me). This was followed by a tasting experience of 4 of their wines (2 Brunellos), paired with a very nice lunch, antipasto and a wonderful, home made pasta. Of course, the best part was getting to meet so many fellow travelers during the lunch. It started down pouring as we headed back out to the car, so we all stayed inside for a while longer. There was no feeling of being rushed out of there because “our time was up”. This trip far exceeded expectations and was a great value at the offered price. This is a trip I will do again the next time I come back to the area.

Hot Air Balloon Flight Over Tuscany from Siena

Suzanne_S, May 2026

Great customer service with Renato

Even though I wasn’t able to do my balloon ride due to inclement weather I would still very much like to pay my sincere compliments to the tour operator, Renato. He provided such excellent customer service…his genuine sense of caring and concern, his responsiveness and helpfulness all makes me definitely want to try to book another ride with him upon my return to Tuscany. Renato is a credit to Viator!

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!!