All Siena Tours &amp; Excursions in 2026

Siena to Rome: Orvieto and Montepulciano Transfer Tour

7 hoursFree Cancellation

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.

Chianti Vespa Tour

4 hoursFree Cancellation

Taste your way through the most delicious private food tour of Siena as you immerse yourself in Tuscan culinary culture with a knowledgeable local host. Indulge in six or 10 iconic treats, including pastries, espresso, and savory bites, while exploring favorite local spots and must-see landmarks like Piazza del Campo and Torre del Mangia. Along the way, discover the rich flavors and history that make Siena unforgettable.

The Most Delicious Private Food Tour of Siena: 10 Tastings

3 hoursFree Cancellation

Two magic hours to discover the city with Your children! Children and adults will learn the city's history having fun and being enriched by anecdotes and legends from the Middle Ages! Magic is hiding in plain sight.... Stroll around the streets of Siena to discover the mysteries, reach the ancient castle and discover the symbol of Siena, the she-wolf, which from the top of its columns protects us. Learn about the 17 districts that we call Contrade and find the animals that represent them. The Contrade participate to the horse race twice a year, an incredible event! Have fun to watch the videos, find the stables where the horses sleep for four days and the little fountains hidden through the streets where the Sienese are baptized.

Siena Family Tour

2 hoursFree Cancellation

Discover with me the unknown and most fascinating Siena with this unique and unusual tour. SECRET SIENA WALKING TOUR, is my favorite to discover history, art and architecture of this wonderful medieval town,away from the crowded tourist routes. Uncover hidden squares, medieval alleys, 14° century perfectly preserved palaces, courtyards and ancient fountains with bewitching legends Enjoy the breathtaking views of Siena, perfect for unforgettable photos and peaceful and suggestive corners. Learn the stories about ancient noble families, medieval pilgrims and ancient disappeared monasteries Explore the territory of a Contrada to know the history of Palio race and visit, if you like, its private museum that I can book for you( tickets not included).

Secret Siena Walking Tour

2 hoursFree Cancellation

Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch

6 to 8 hoursFree Cancellation

Chianti Classico E-Bike Tour

5 to 6 hoursFree Cancellation

Explore Val d’Orcia, a UNESCO World Heritage site known for its stunning landscapes, art, and rich food traditions on this private tour. Visit Montalcino, home of the renowned Brunello wine, where you'll enjoy a guided winery tour and lunch. Then, head to Montepulciano, a medieval city with Renaissance palaces and sweeping valley views, famous for its Vino Nobile wine. Enjoy wine tastings in both towns while taking in their historical and scenic beauty.

Private Montalcino and Montepulciano Tour from Siena

7 to 8 hoursFree Cancellation

Embark on an adventure that will take 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 (tasting included) and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition, the experience includes a guided tour of one of Chianti's most characteristic castles, the castle of Brolio, from which you can take in magnificent panoramic views to the vineyards and the city of Siena. To experience the most out of the territory, we'll book lunch at a local family owned restaurant where you, in addition to enjoying its tranquility and warm welcome, can savour the dishes of the Tuscan tradition. The way back is mainly descending and the guide will stop in magnificent sightseeing spots before getting back to the starting point.

During the tour, there'll be lots of time to relax and to enjoy the good company while cycling in the famous Eroica Gravel roads of the Chianti.

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

7 hours 15 minutesFree Cancellation

Explore Chianti’s backroads and beautiful vistas while traveling in a private 4WD on this tour with hotel pickup. Soak up the scenery while a driver handles the country roads, stopping at off-the-beaten-track cellars and cantinas to taste several Chianti Classico wines along with Tuscan olive oil, honey, and other specialty products. Balance out all that wine with a traditional Tuscan lunch at a scenic family estate.

Private Off Road Wine Tour in Chianti from Siena

Private Off Road Wine Tour in Chianti from Siena

6 hoursFree Cancellation

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

Chianti and Castles Tour from Siena Small Group

5 hoursFree Cancellation

Experience the enchantment of Siena with an enthusiastic local guide on this private tour. Discover famous sites such as Duomo di Siena, Piccolomini Library, and Piazza del Campo, while revealing secret treasures on your journey. This personalized, adjustable tour allows you to explore Siena in your style, featuring expert suggestions and captivating narratives that animate the city’s history.

Highlights & Hidden Gems of Siena Private Tour - Duomo Included

3 hoursFree Cancellation

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

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

2 hours 30 minutesFree Cancellation

PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience

7 hoursFree Cancellation

Experience a side of Italy rarely available to visitors when you take a cooking class in the Chianti wine region. During your private session, discover the secrets of Tuscan cuisine, from sauces to tiramisu. After dining on the food you just learned to make, continue on to a vineyard for a complimentary wine tasting and pairing lesson. Round-trip transport from Siena is included for your convenience.

Private Cooking Class in Chianti from Siena

Private Cooking Class in Chianti from Siena

5 hoursFree Cancellation

Explore the fascinating world of Tuscan sparkling wines with us! Book our unique experience now and discover what makes our business so special. During the guided tasting, you will be immersed in the art and science of sparkling wine production. Our wine educators will guide you through an exclusive selection of three Tuscan sparkling wines, each produced with a different production method: the classic method, the charmat method and the ancestral method. This experience will not only allow you to savor the unique flavors of these high-quality sparkling wines, but will also give you an in-depth understanding of the different techniques used in their production. You will be fascinated by the diversity of aromas and complexity that each production method adds to the wine.

Precision and Mastery: The delicate riddling process

Exclusive Wine Tasting in the Historic Center of Siena

1 hourFree Cancellation

Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at a few wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop.

Private Off Road Wine Tour in Chianti

6 hoursFree Cancellation

Private wine tour of Chianti

6 to 8 hoursFree Cancellation

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

Private Grape stomping at Chianti Farmhouse

4 hoursFree Cancellation

Inject a bit of adventure into your wine tasting experience with this ATV tour through the vineyard-covered countryside surrounding Siena. Take in views of the UNESCO-listed Crete Senesi landscape as you zip over the hills behind your guide, following unpaved trails through woods and fields. End at a family-run cellar to sample Tuscan wines paired with local gourmet specialties and snacks.

Wine Tasting ATV tour in Tuscan countryside

Wine Tasting ATV tour in Tuscan countryside

4 hoursFree Cancellation

Learn to cook Tuscan-style with this small-group cooking class at a farmhouse in the Val d’Orcia hills. Under the expert eye of your local host, you’ll use farm-fresh ingredients to make pasta from scratch, a roasted meat dish that’s typical to the region, and a classic tiramisu. Hear about the culinary traditions of Tuscany, Umbria, and Lazio as you cook, then eat with your host and group.

Cooking Class at a Farmhouse in Val d'Orcia Tuscany

5 hoursFree Cancellation

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

Private Guided Tour of Siena with a Licensed Local Tour Guide

2 hoursFree Cancellation

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

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!

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.

Siena: A Wine Tour and Tasting Experience

Barry_K, Oct 2026

Amazing value with brilliant commentary and excellent pairings

It was an amazing tour that utilized the three hours with brilliant information, extraordinary tastings, great food in a warm, friendly atmosphere. Dario explained that winemaking is a science and we learned so much. This is a well priced time worthy tour that we would suggest to anyone to sign up for.

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 Brunello di Montalcino Wine-Tasting Trip from Siena

Geoff_H, Sep 2026

A great tour

We enjoyed this tour immensely. It was a little chaotic at the meeting location sorting out the groups but once we were assigned our driver and van the day could not have been better. We had a small group of 6 people total and our driver, Corrado, was very knowledgeable, attentive and engaging. He told us about the wine region on the way to the first tasting. The first tasting started with a tour and explanation of the viticulture practices of the winery followed by a tasting of 4 bottles. The second tasting included lunch at the home of the wine maker which was very good. The day ended with a third stop at a bio-dynamic winery, again with a tour and tasting. It was a long day, we didn't get back to Sienna until 6 or so but so enjoyable. I would highly recommend this tour to any wine lover or someone who is interested in becoming a wine lover.

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!

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

Melissa_A, Aug 2026

Highly recommended

Hands down one of the highlights of our trip! My dad and I took a food tour in Siena with Jacopo, and he was incredible. Jacopo is amazingly knowledgeable, sharing fascinating local history and culinary stories alongside delicious tastings. Be prepared for a bit of a walk—which was a great way to explore the town and burn off some of the food! I can't recommend Jacopo and this tour highly enough

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!!