All Siena Tours &amp; Excursions in 2026

Skip the Line: Siena Duomo and City Walking Tour

2 hoursFree Cancellation

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

11 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.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

E-Bike rental in Tuscany

1 dayFree Cancellation

Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

2 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.

Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

Price varies by group size

Siena: A Wine Tour and Tasting Experience

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.

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 hoursFree Cancellation

Siena Pasta & Tiramisu Cooking Class With Wine by Cooking Italy

There are places you visit and others you live. A few minutes from Siena, between the Chianti hills and the Crete Senesi, the experience slowly takes shape on our panoramic terrace, in the shade of an ancient white mulberry tree. What makes it special is the opportunity to taste our wines directly with those who produce them, in a family-run cellar where each bottle is born from the link with the territory. It is not a standard tasting, but an authentic moment made of stories, flavors and genuine hospitality. The wines tell the story of the territory, the typical Tuscan dishes accompany them and the landscape completes the experience. If you are looking for a real meeting with Tuscany, made of details, hospitality and dedicated time, this is the right place.

Classic Wine Tasting with Traditional Tuscan Products

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

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

Explore Siena at your own pace with a self-guided walking tour on your phone. You get a clear map of all 12 stops, simple directions through Google Maps, and short audio stories you can play when you reach each location. The route covers Siena's historic center, from Piazza del Campo to Monte dei Paschi di Siena, passing sites like the Palazzo Pubblico, Torre del Mangia, and Fonte Gaia. Start anytime, pause whenever you like, and explore freely. No groups, no schedules. Audio and text available in 7 languages.

Self Guided Walking Tour of Siena

2 hoursFree Cancellation

Special Offer

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

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

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.

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

What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci, a family winery surrounded by the rolling hills of Montalcino. Guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the traditions, craftsmanship and passion behind Brunello di Montalcino production. The experience continues with a carefully curated tasting of premium Tuscan wines paired with a traditional Tuscan lunch featuring local specialities and fresh handmade pasta, creating a journey that combines wine, food and landscape in a truly authentic way. Far from crowded commercial tours, this immersive experience offers a refined and memorable taste of Tuscany in a relaxed and elegant setting. Each tasting is led by expert sommeliers, transforming every glass into a deeper journey through the world of Brunello di Montalcino.

Montalcino: Brunello Wine Tasting & Tuscan Lunch

Discover the charm of the olive grove with a visit to the oil mill, where you can learn the olive oil production process. This tour includes a tasting of local typical products, such as wines, cheeses, and cured meats, all from the region. Immerse yourself in authentic flavors while exploring local culinary traditions in a suggestive and welcoming environment. Guided tour of the olive grove and the oil mill to learn about oil production Tasting of local wines, cheeses, and cured meats - Discover the local culinary traditions in a welcoming atmosphere A unique opportunity for food and local culture lovers

Olive Grove Tour with Wine and Local Product Tasting

5% savings

from

$21$20

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.

Hot Air Balloon Flight Over Tuscany from Siena

Hot Air Balloon Flight Over Tuscany from Siena

Price varies by group size

Montalcino: Brunello Wine Tasting Experience

There are many ways to spend an evening in Tuscany, but few allow you to experience it from the inside. Just a few minutes from Siena, between Chianti and the Crete Senesi, this experience takes you through vineyards, cellars, and history, guided directly by the people who produce the wine every day. What makes it special is the combination of a visit to a family-run winery, a tasting of our wines, and a traditional Tuscan dinner served at sunset on a panoramic terrace overlooking two of the most fascinating landscapes in the Siena area. It is not just a wine tasting or a dinner, but an authentic experience where wine, territory, tradition, and hospitality come together in a relaxed and genuine atmosphere.

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Just a few minutes from Siena, San Giorgio a Lapi offers an authentic experience in the heart of Tuscany, in a unique location between Chianti Classico and Chianti Colli Senesi. What makes this tour special is the opportunity to experience a family-run winery firsthand, guided by the people who cultivate the vineyards and produce the wine. In addition to visiting the vineyards and wine cellars, you will discover the 11th-century Church of San Giorgio a Lapi and conclude your experience on our panoramic terrace overlooking the hills of Chianti and the Crete Senesi, where you will enjoy a guided tasting of 4 wines and a traditional Tuscan lunch prepared with local ingredients. A journey that combines wine, history, landscape, and genuine Tuscan hospitality.

Siena: Chianti Wine Tour with Wine Tasting and Lunch

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?

Siena Walking Tour with Audio and Written Guide by a local

4 to 5 hoursFree Cancellation

Price varies by group size

Italian Opera in Siena Experience

1 hour 20 minutesFree 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

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.

Small-Group San Gimignano and Volterra Day Trip from Siena

Alicia_H, Sep 2026

Excellent do it!

This was really fun tour and I would highly recommend it to anyone thinking about taking it. It was totally worth the money because you are taken around to three separate cities and it’s an all day eight hour tour. I went with my husband and I would recommend that you take Dramamine or motion sickness medication with you for the ride back if you ever get carsick and go easy on the wine tasting during the day because the curvy roads may make you sick. that aside however, the views from the van were beautiful. the van was clean. The guide Kiko was amazing and told us so much history and he was so kind. We loved visiting the winery and we really loved visiting the artisan at the shop in Volterra. We even bought a few items from him that we will treasure. We loved all three cities. They were very interesting and we had plenty of time in all three. I would highly recommend this tour. We also took the other tour to Pienza and Montepulciano. and we preferred the tour to Voltera/ San Gim. over the other one. That tour was fine. It just wasn’t as interesting.

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!!

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.

Small-Group Montepulciano and Pienza Day Trip from Siena

Kevin_B, Sep 2026

Best tour while in Italy...

Best tour while in Italy given by a fantastic tour guide ( Marco). Enjoyed all the stops along the way and Marco was very informative. Lunch was good but was light ( more like charcuterie) with wine and biscotti for dessert. Some hills and steps to climb, Marco was good to try and minimize these. Would highly recommend!!

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.

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

tashhackett, Sep 2026

Perfect way to see Siena and enjoy its delicious food!

Valentina was the perfect guide - friendly, informative and kind. Loved walking around Siena and getting some history about buildings, statues and hidden away streets that we would have missed on our own. And then there’s the food …. delicious and was lovely discovering local restaurants that (again) we would have missed had Valentina not showed us. We took up the drink card option so was lovely to enjoy a local glass of wine with lunch and a small extra treat at the last dessert stop. Highly recommended this tour.

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

Sarah_G, Jul 2026

Wonderful day trip, lunch and wine tasting

The tour was wonderful, we loved San Gimignano with its amazing towers. We had our own free time to explore all the stops. Our guide Ricardo was excellent. He gave us lots of interesting information on the places we were visiting and made sure we all knew the time and place we were meeting. He guided us through Sienna. The wine tasting was fabulous, we tasted 4 glasses of wine , 2 Spumante. The food was great. This is an 11 hour trip but it was only a little walking. We loved it. Christina helped Ricardo with the tour. It was really good value for money and I highly recommended doing it. Bellissimo!

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!!