All Siena Tours &amp; Excursions in 2026

Exclusive Wine Tasting in the Historic Center of Siena

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

The academy is much more than a cooking school where you can learn traditional dishes, it is an authentic experience that blends tradition, local flavors and Tuscan hospitality. We stand out for the careful selection of ingredients of the territory, many of which are zero km. Our location is the very framework of the experience. Immersed in the medieval streets a few steps from Piazza del Campo, it gives our guests a unique and suggestive atmosphere where every experience is accompanied by the beauty of Siena.

Fresh Pasta & Authentic Italian Sauces

3 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

3 hoursFree Cancellation

Open the doors of the Sienese countryside on horseback and immerse yourself in the breathtaking landscapes of the Tuscan countryside. Cross vineyards, rivers, olive groves and roads with cypress trees. See and touch the flora and fauna of the Sienese countryside with a guide who will explain the various plants and animals and the history of the places you will encounter during the tour. The walks in the Sienese countryside are suitable for everyone, from beginners to experts. The horses used for the tours are well trained and calm, suitable for everyone. Stop for a picnic in the shade of the river in the Siena area or for a tour and tasting in a winery. Spend an unforgettable day and discover Tuscany with different eyes as you ride your horse, seeing and touching the historic countryside and traditions of Siena.

Horseback Riding in the Tuscan Vineyards

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

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

Private Ebike Tour in Chianti

6 hoursFree Cancellation

VIP Chianti, Brunello wine & Pienza with lunch From Siena

8 to 9 hoursFree Cancellation

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

A two hours enchanting walk, discovering Siena most beloved places. Start in front of the Basilica San Domenico, where the relics of St. Catherine are kept, then continues towards her ancient house. Stroll in the characteristic streets and reach the Cathedral. Decide with your guide if you want to enter shortly to see the unique marble floor and artworks by Donatello, Bernini and Michelangelo. Arrive at the famous Piazza del Campo, the main square, where the Palio (horse race), takes place twice a year. Discover this medieval tradtion and understand why it is so important for the Sienese. The Town Hall is an example of Italian architecture, which houses the important city museum. Admire also the Joyfull Fountain and listen to funny anecdotes about the mysterious river called "Diana". At the end of the tour visit our location in an historic palace, Palazzo Scotti, where you can take amazing pictures from our exclusive windows overlooking Piazza del Campo. Relax and enjoy your time!

Siena Tour and exclusive window on Piazza del Campo

Siena Tour and exclusive window on Piazza del Campo

2 hoursFree Cancellation

Small group Chianti Classico & Brunello wine region from Siena

5 hours 30 minutesFree Cancellation

Explore Quaint Villages and Timeless Landscapes Our journey will take you off the beaten path, winding through both lesser-known hamlets and iconic landmarks alike. Immerse yourself in the rich history and culture of each village we visit, from hidden gems tucked away in the countryside to well-known destinations steeped in tradition. Capture Every Moment, Embrace Every View As we traverse the rolling hills and winding roads, there will be ample opportunities to pause and soak in the panoramic views. Experience the Joy of Open-Air Travel Feel the sun on your face as you cruise through the Val d'Orcia on your Vespa. This isn't just a tour – it's an immersive journey into the heart of Tuscany's natural beauty. Let the open road be your guide as you embrace the freedom of outdoor exploration. Don't Miss Out on This Unforgettable Experience Join us for a Vespa adventure like no other and discover the magic of Val d'Orcia in a whole new way.

Discover the Hidden Gems of Val d'Orcia by Vespa!

Siena Historic Center (Siena Centro Storico) is a UNESCO World Heritage Site for its glorious Gothic architecture and rich culture. Join an official, licensed guide who specializes in the city and understands it deeply on this in-depth tour. You'll see the signatures: Piazza del Campo, home of the annual horse race, and Siena Cathedral, with its marble stripes. But you'll also delve further into Siena's medieval neighborhoods and local lifestyles.

2 hour Siena Private Guided Walking Tour

2 hour Siena Private Guided Walking Tour

2 hoursFree Cancellation

What makes this experience truly unique is the opportunity to enjoy an authentic Tuscan dinner among the vineyards of Paradiso di Cacuci, surrounded by the peaceful atmosphere and timeless beauty of the Montalcino countryside. As the sun sets over the rolling hills, guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the passion and traditions behind Brunello di Montalcino. The evening continues with a curated tasting of exceptional Tuscan wines paired with traditional cuisine, creating a journey where every glass and every dish reflects the soul of Tuscany. From Brunello Riserva selections to handmade pasta and authentic Tuscan flavours, the experience combines elegance, intimacy and a true sense of place. Far from crowded restaurants and commercial tastings, this is a refined and immersive evening designed for those seeking exceptional wines, authentic food and the unforgettable atmosphere of a dinner in the vineyards under the Tuscan sky.

Montalcino: Brunello Wine Tasting & Tuscan Dinner

3 hoursFree Cancellation

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

4 hours 30 minutesFree Cancellation

Siena has one of the most intact medieval cityscapes in Italy, and with this walking tour, you can take in the hill town’s top sights in just two hours. Skip the hassle of following a map and instead head straight to the highlights with a guide. Stroll past Piazza del Campo, the town hall, and the Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.

Discover Siena: Guided Walking Tour and Cathedral Visit

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and Taste’ will introduce you to the local food and wine and to the fascinating world of sustainable wines. A journey through the secrets of viticulture in the age of climate change. Designed for all those who love fine wine and food, this intimate experience is for a maximum of 8 people and is led by one of the winery's owners. The winery tour will be followed by a guided sensory tasting session to capture and break down the different organoleptic profiles that participate in the complexity of our vintage and private reserve wines. Finally, you will enjoy a full lunch with the right food and wine pairings that will delight your palate and nourish your soul.

Exclusive Wine Tour and Tasting Experience in Siena

3 hours 30 minutesFree Cancellation

Combine three of Italy’s most vital delights—wine, landscapes, and history—on this tour of the 15th-century Castello Tricerchi Montalcino wine estate. Exploring in a group no larger than 15, discover 600 years of history, including the chapel, the vineyards, and the cellars. Round off your visit with a tasting of three signature wines—Brunello di Montalcino, Rosso di Montalcino, and a Toscana IGP—paired with delicious local nibbles.

Historic Castle & Brunello Wine Experience in Montalcino

Skip the Line: Siena Duomo and City Walking Tour

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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

Ewen_M, Oct 2026

The best walking tour we have done

An informative and entertaining tour of the old town and the two major churches. Our guide (Michael) was very knowledgeable and explained the local passions for the horse race as well as sharing an understated but deep understanding of the art and culture of the city. We have taken walking tours in each of the 4 cities we have visited so far, and this was the best.

Small-Group Montepulciano and Pienza Day Trip from Siena

Gary_B, Oct 2026

Fabulous excursion

Our guide was fantastic and very knowledgeable about everything we were doing. The scenery on the trip was super. The fellow passengers were very convivial. The tones we stopped in were breathtaking. I couldn’t imagine anything being better on this tour.

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

Siena: A Wine Tour and Tasting Experience

Maureen_B, Oct 2026

Small, friendly winery, near Siena

One of our favorite winery vists. This is a small winery, just outside of Siena. We took a taxi to and from, I believe it was on the order of €12-€15 one way. Our guide was Lorenzo, the wine maker. He was very informative and very engaging. We got the wine tasting plus light lunch and it was a great combination. The food was very good. And we shipped some wine hime! We totally recommend this visit

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

David_C, Oct 2026

Fun experience well worth it

We were staying in Montalcino and drove the short distance to this winery. The tour was informative and fun. The host/guide was very knowledgeable and friendly. The grounds are beautiful with wonderful views. We had a fantastic weather day for this too. The wines were good. Brunello is one of my favorite wines ever since we visited Montalcino on a day trip 4 years ago. The food was good and we enjoyed talking with the other people on the tour. Highly recommend this experience.

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 Street Food Tour With 4 or more Tastings

Michael_N, Aug 2026

The best tour and guide you will ever have!

Veronica was the best guide we have ever had. We’ve traveled the world and have gone on many tours, high-end, on the lower side, in the middle. She is the absolute best and went above and beyond all of our expectations. Even after the tour, she was extremely accommodating and made us feel like a local. I would never use anyone else ever. Absolutely 10 out of 10 the best you’re gonna get.

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

Kennedy_G, Aug 2026

#TuscanyLife

I really enjoyed this trip and it was a nice break from being in the city. It's a typical bus tour where everyone piles on from one stop to the next, but it gives you a great opportunity to visit some interesting sites. All the stops were great, including lunch at a vineyard with wine tasting. However, Siena was probably our favorite stop. Beautiful city and full of energy as the city prepared for the upcoming Palio di Siena horse race.

Siena: Chianti Wine Tour with Wine Tasting and Lunch

Erika_S, Aug 2026

An authentic lovely experience!

Super convenient and lovely winery to visit! Even if you don’t have a car, a taxi from Siena is a good option and not pricey. The winery itself is lovely, Elena did the tour and explanation of the grapes and the operation of the winery. It is a family owned business, so it is very authentic with a unique charm. The meal prepared by Luca, one of the sons, was perfectly balanced and with great wine pairings. Overall a great authentic experience if you want a taste of true Tuscany.

A Brunello Cooking Class with Vineyards View Winery

Stephanie_R, Jun 2026

Tuscan Experience

We had a great time at this cooking experience. We were greeted by Alice who gave us an informative tour of the castle and the winery. She was so kind and interested in sharing as well as answering any of our questions. The cooking part of our day was great. Yummy wine and fun Italian music was the perfect start to our lesson with Cat. We worked together with another family to create two kinds of pasta as well as tiramisu. While making, rolling and cutting our pasta, we were treated to a beautiful view out of the windows. After we completed our pasta, we sat down together to a lovely lunch (feeling proud to have made it ourselves) with more delicious wine. It was a fantastic way to immerse ourselves in the Tuscan life! Thank you for a fun day for our group.

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!!