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

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

E-Bike rental in Tuscany

1 dayFree 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

Discover Siena's perfectly preserved medieval splendor with our self-guided audio tour app, allowing you to explore this Tuscan jewel at your own pace. Begin at the magnificent Piazza del Campo, the shell-shaped square that hosts the legendary Palio horse race and remains the heart of Sienese civic life after seven centuries. Marvel at the soaring Torre del Mangia and the Gothic grandeur of the Palazzo Pubblico, then ascend to the heavenly Duomo where Pisano's pulpit and the Piccolomini Library showcase Renaissance mastery. Wander through the contrade neighborhoods where medieval rivalries still define local identity, their fountains, flags, and parish churches marking territories unchanged for centuries. Discover the Pinacoteca's golden altarpieces and the Basilica of San Domenico where St. Catherine's head is reverently preserved, then lose yourself in the winding vicoli that reveal unexpected piazzas and artisan workshops.

At Your Own Pace: Discovering Siena & Tuscany

9 hours 30 minutesFree Cancellation

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USD 3

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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

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

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

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

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

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

When you’re in the Tuscan city of Siena, don’t miss the chance to discover its famous wines and enjoy some local food, too. This small-group wine tour visits a winery near Siena’s historical center, and gives the lowdown on the winery’s organic production methods. After visiting the vineyard, you’ll savor a meal made with local produce along with samples of five organic wine varietals. Numbers are limited to 12 per group.

Guided Winery Tour and Wine Tasting in Siena

2 hours 30 minutesFree Cancellation

Siena Pasta & Tiramisu Cooking Class With Wine by Cooking Italy

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

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USD 21USD 20

Experience the charm and history of Siena on a private walking tour led by a passionate local guide! Wander through its winding streets, lively squares, and hidden corners as you uncover the stories, culture, and traditions that make this Tuscan city so enchanting. Whether you choose a short 2-hour stroll or a full 6-hour exploration, your guide will tailor the tour to your interests, sharing local insights, secret spots, and authentic experiences along the way. Discover Siena like a true local and enjoy an unforgettable journey at your own pace.

Siena Private Walking Tour with a Local

1 to 6 hoursFree Cancellation

Price varies by group size

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

Hidden Castles & Chianti Wine Experience– Small Group

5 hoursFree Cancellation

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

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. 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

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

Small-Group Montepulciano and Pienza 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

Karyn_I, Oct 2026

Perfect Day in Tuscany!

Outstanding! Hands down, the best day trip/tour we took while in Italy! Our guide/driver Keko was fantastic…. Knowledgeable, interesting, friendly and warm! He took us to beautiful, charming locations and it ended up being our favorite day of the two weeks we spent in Italy. Perfect! Thank you Keko!

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

Amar_P, Oct 2026

This is a beautiful wine...

This is a beautiful wine immersive experience! Our guide Paolo was beyond amazing with his personality, knowledge, and passion for Italy and the region! We heard great stories of wine, family and tradition from all 3 wineries visited, none were tasting rooms in the city but a true vineyard experience

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!

Skip the Line: Siena Duomo and City Walking Tour

cindief52, Oct 2026

Best of the best

The best way to see Siena is this tour! The guide was so knowledgeable and friendly and so in love with her city that you could really feel what it was like to live there. From huge churches to tiny lanes to history to daily experience she made us fall in love with Siena. This was probably the best tour of our whole two week trip.

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, Sept 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!!

Siena: A Wine Tour and Tasting Experience

Kim_P, Sept 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.

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!

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

Aidan_F, Aug 2026

Day trip in Tuscany

This was such a fun day trip through the Tuscan region, with wine tasting, a delicious lunch, and plenty of beautiful scenery along the way. The highlight for me was definitely spending the afternoon exploring Siena. A great way to experience the best of Tuscany in one day!

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

Jennifer_B, June 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!

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!!