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

1 hour 30 minutesFree Cancellation

E-Bike rental in Tuscany

1 dayFree 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

Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

2 hoursFree Cancellation

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

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

1 hour 30 minutesFree 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

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 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

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

Siena Pasta & Tiramisu Cooking Class With Wine by Cooking Italy

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.

Special Offer

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

10 to 11 hoursFree Cancellation

An authentic journey through the heart of Tuscany unfolds with a truffle hunting experience, led by a skilled truffle hunter and his loyal dog. Wander the serene woodland paths, witnessing the ancient art of truffle hunting and uncovering the secrets behind this culinary treasure. Following the hunt, indulge in a guided tasting of exquisite wines, oils, and vinegars from Poggio ai Laghi, enriched by the enchanting legend of Donna Ava. A delightful Tuscan lunch completes the experience, featuring a truffle-infused appetizer, a pasta dish, and traditional cantuccini. This intimate adventure blends nature, tradition, and gastronomy for an unforgettable day.

Truffle Trail and a Taste of Tuscany

2 hours 45 minutesFree Cancellation

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

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

Siena is one of Tuscany's most fascinating hill towns, but most visitors check off a handful of famous sights and move on. Get a more in-depth, personalized introduction to this medieval city on this private walking tour, fully customized to your pace and interests. Focus on the historic architecture, traditional Palio festival, or local food scene, or combine culture and cuisine to create a unique itinerary. Choose an express tour of just a few hours or a full-day deep dive that takes you to little-known gems most tourists miss.

Siena Private Highlights and Hidden Gems Walking Tour

2 to 6 hoursFree 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.

San Gimignano, Chianti, and Montalcino Day Trip from Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena

11 hoursFree Cancellation

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

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

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Private Tour: Secret Siena Walking Tour

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

Small-Group San Gimignano and Volterra Day Trip from Siena

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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

Alicia_H, Sept 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.

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

Kevin_B, Sept 2026

The scenery of the tuscan...

The scenery of the tuscan hillsides were beautiful although an hour and a half ride to the first winery. Interesting tour of the first winery with tasting in the owners home which was beautiful! The second winery was our favorite with Gianni Bernazzi’s wines and 5 star lunch! He is an excellent chef!! The last winery had a beautiful view of the hills. It was a full day and a lot of Brunello wines.

Skip the Line: Siena Duomo and City Walking Tour

MARTI_W, Sept 2026

Great Tour

This was a great city tour! We learned a lot about the Siena contrades and the horse race. The Duomo was beautiful! The location to the tour on the app took us right to the starting/meeting point. Leave plenty of time to park and walk to meeting point. Great tour and neat to learn about Siena!

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

John_Q, Sept 2026

An evening of exceptional wine tasting

This tour was one of the most knowledgeable and informative tours. The staff and hosts were so friendly and attentive and accommodating. This winery is family owned and so very good. Their tour includes several tasting, walking tour and a fantastic dinner. We would definitely recommend this tour for anyone who enjoys a great relaxing experience that’s engaging and fun

Small-Group Montepulciano and Pienza Day Trip from Siena

Lisa_C, Sept 2026

This tour will add dimension to your experience of Italy beyond the big city attractions you’ve already done.

We got a sampling of several very beautiful towns in Tuscany and participated in varied activities over a full day: driving through the Tuscan countryside, walking through very old, very picturesque little towns and exploring their historical and amazingly well decorated religious buildings, eating a good pasta lunch with cheeses and wines at, and enjoying walking around an organic farm with its charming animals. We got to enjoy 3 lovely wines at a winery. We were safely driven, informed, and entertained by Georgia who is a talented tour guide.

Siena Pasta & Tiramisu Cooking Class With Wine by Cooking Italy

Christine_G, Sept 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

Maryna_H, Sept 2026

We had such a wonderful...

We had such a wonderful experience on this wine tour! Dario was an amazing guide - friendly, knowledgeable, and made the whole experience very enjoyable. The wines were excellent, the food pairings and presentation were fantastic, and everything was very well organized. We enjoyed every part of the tour and had a truly memorable time. Highly recommended if you’re looking for a great wine and food experience in Tuscany!

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

tashhackett, Sept 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!

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

nora_m, Jun 2026

So much more than a wine-tasting!

More than a corporate wine tour, this felt like a home visit with friends. Alice was a warm and wonderful guide who explained the history of the castle, the origins of winemaking in the region, and daily life in her part of Tuscany. A wonderful, unexpected afternoon. And of course, the wine was top-notch.

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

Hanna_A, Mar 2026

Amazing

This was a great experience. My second time on a hot air balloon and it was just as amazing as the first. What a unique and peaceful easy to experience the Tuscan countryside. This team was very experienced with excellent communication before the experience and during it as well, and very friendly staff. The breakfast picnic after landing was perfect.