All Siena Tours &amp; Excursions in 2026

Private Guided Tour of Siena with a Licensed Local Tour Guide

Private Ebike Tour in Chianti

6 hoursFree Cancellation

VIP Chianti, Brunello wine & Pienza with lunch From Siena

8 to 9 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

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

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

Tuscany is known for its excellent vintages, but the world of Tuscan wine can be overwhelming for a novice. With this informal wine class, you’ll get your bearings and learn to recognize the most important and storied wines of Tuscany. Delve into the history of Tuscany’s wine production, discover the different wine-producing areas and grapes, and sample a number of reds and whites from the region.

Wine Class - Tuscan Classics

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

1 hourFree Cancellation

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

This is a city walking tour that will give you the occasion the see this city from the eyes of a local. Your Guide is a certificate professional that has lived and worked in Siena for many years and can give you a full immersion view on the traditions of the city. We will discover together the myths, legends, and secrets of this medieval town and we will have the occasion to see very iconic neighborhoods and street where normally locals spend their time with friends and family. You will try 3 different flavors of Artisan Gelato & Tuscan wines. At the end of the tour our guide if requested will give you some great recommendation like the best restaurants or any other activities to do in Siena.

Siena walking tour with Gelato & Prosecco

1 hour 30 minutesFree Cancellation

PRIVATE TOUR: Savor Exquisite Wines: Brunello & Nobile Wine Tour

9 hoursFree Cancellation

Embark on a delightful journey through the picturesque Chianti region on a private tour from Siena. Combining regional cuisine, local history, and iconic landscapes, this excursion enables you to get the complete Tuscan experience in a single day. With highlights including a family-run winery, Monteriggoni Castle, and the hill town of San Gimignano, this robust, well-paced itinerary lets you savor your limited vacation time without feeling hurried.

San Gimignano
(Original photo of our tours)

"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings

8 hoursFree Cancellation

5% savings

from

$286$271

Enjoy a wine experience in the heart of Val D'Orcia, surrounded by the most authentic Tuscan countryside. Together with Tatiana, the owner of Poggio del Moro, or our oenologists, you will explore the Poggio del Moro estate - from the vineyards, to the oil mill, to the cellar and the barrique cellar - and you will learn the production process of our natural wines, free from pesticides and unnecessary production interventions. Poggio del Moro is an out of the ordinary boutique winery, an extraordinary open-air art gallery. In addition to our excellent wines, here you will find contemporary art exhibitions or artistic performances, which you can observe while visiting the cellar or tasting your wine in relaxation, an absolutely original and refined experience in an intimate and exclusive setting!

2 Hours Visit and Wine Tasting with tastings in Val D'Orcia

2 Hours Visit and Wine Tasting with tastings in Val D'Orcia

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

Private Montalcino and Pienza Tour from Siena

6 hoursFree Cancellation

This customized day trip pairs the otherworldly landscapes of southern Tuscany with the region’s frozen-in-time villages and prized flavors. Relax and take in the views from a luxury vehicle while a private guide and driver handles the country roads. Taste famed Brunello wine in Montalcino and Pecorino cheese in lovely Pienza, visit a medieval monastery, and get hand-picked recommendations for an authentic Tuscan lunch.

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully licensed Mercedes van with air conditioning for a smooth and relaxing ride. Accompanied by a professional driver-guide-certified sommelier, fluent in English and Italian born and raised in the Montalcino area. Travel through the stunning Val d’Orcia admired worldwide for its rolling hills and iconic landscapes. The highlight of the tour is an exclusive visit to a family-owned, organic Brunello winery, where you will walk through the vineyards, tour the cellars, and enjoy a guided tasting of selected red wines, including the celebrated Brunello di Montalcino, accompanied by a tasting extra virgin olive oil. The experience concludes with free time in the medieval town of Montalcino, the heart of the Brunello wine region, where you can explore historic streets, admire monuments, and browse charming local shops at your own pace.

Brunello di Montalcino wine experience with a sommelier

Brunello di Montalcino wine experience with a sommelier

5 hoursFree Cancellation

Visit Monteriggioni, San Gimignano, and more on a customizable 8-hour private tour. After pickup from your Siena hotel, discover the Tuscan countryside in a luxury vehicle, complete with complimentary WiFi and refreshments. Given that you’re in the heart of Chianti Classico, a tasting at a local winery is highly recommended. But you're free to pick and choose which locations you’d like to visit and your guide will happily oblige.

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from SIENA

Fascinating walk to discover Siena, the most famous monuments and the least known and most precious places. We will walk through alleys and medieval streets, we will talk about Palio and Contrade, noble palaces, famous painters, Francigena and illustrious characters. Towers, medieval houses, squares and ancient sources. Monte dei Paschi, the famous Duomo with its masterpieces, the Ancient hospital and the noble public palace. I wait for you for a pleasant and interesting private tour of the city of Siena

Siena private guided tour for families

The Tuscan countryside is a premier hiking destination, but navigating unfamiliar trails and country roads on your own can be daunting. On this private hiking tour, explore the rolling hills and vineyards stress-free with a guide leading the way. Meet in Siena and transfer to the trailhead by minivan, setting off through the verdant countryside and past rustic villages. Take a break to relax over a classic lunch of Tuscan treats and then travel via minivan to San Gimignano for a stroll through town and along a stretch of the Via Francigena before the return ride to Siena.

Private Tour: Guided Hike in Tuscany with Transport from Siena

7 hoursFree Cancellation

Enjoy an exclusive lunch or dinner in an ancient cave of Etruscan origin, in the heart of a historic restaurant in Siena. Delight your palate with fine wine pairings, surrounded by the millennial charm of a timeless place, transporting you on an unparalleled sensory journey. Treat yourself to a magical evening with a private dinner in an ancient Etruscan cave, accompanied by selected wines that enhance every dish and create unforgettable memories. Discover the timeless charm of an exclusive dinner in an Etruscan cave, where every bite is paired with fine wines for an unforgettable culinary experience in the heart of Siena. Experience the emotion of a unique dinner: a sensory journey through authentic flavors and fine wines, immersed in the suggestive atmosphere of a historic Etruscan cave.

Dinner with wines and typical dishes in a secret cave in Siena

Dinner with wines and typical dishes in a secret cave in Siena

5% savings

from

$270$256

Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.

Private Truffle Hunting in Chianti

5 hoursFree Cancellation

Travel between destinations and visit sights along the way. Stop to visit the medieval fortress of Monteriggioni before spending leisure time in the hill-town of San Gimignano browsing the many stores or savouring the rich cuisine in one of its many restaurants (not included). In the afternoon visit the Chianti town of Greve in Chianti and the picturesque hamlet of Montefioralle before having your Private driver drop you off at your Florence destination.

Private Siena to Florence Chianti and San Gimignano Transfer Tour

Private Siena to Florence Chianti and San Gimignano Transfer Tour

7 hoursFree 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

Small-Group Montepulciano and Pienza Day Trip from 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!

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.

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: 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.

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.

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!!