All Siena Tours &amp; Excursions in 2026 - page 4

Private Tour of Siena Cathedral

(24)

from $162

The hot air balloon tour is a magical experience, a true adventure carried out in total safety by flight professionals. Our pilots, all with great experience, are ENAC certified commercial pilots. They will guide you during your trip, sharing with you detailed information about hot air balloons and satisfying all your curiosities about the flight and its navigation. Don't wait any longer, immerse yourself in this extraordinary adventure.

Hot air balloon over the hills of Pienza, Montalcino and Val D'Orcia

Hot air balloon over the hills of Pienza, Montalcino and Val D'Orcia

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

(21)

from $413

Siena private guided tour for families

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.

(8)

from $271

Per group

Enjoy this private food tour of Siena with a local foodie host

The Most Delicious Private Food Tour of Siena: 10 Tastings

(11)

from $255

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

(10)

from $433

The Montalcino hills are home to some of Tuscany's most prestigious wineries, but sussing out these small producers on your own can be a challenge. On this tour, access a premier family-owned cellar set in a medieval castle for an exclusive guided tour and tasting with a group capped at just 15 people. Learn about the history and production of award-winning Brunello di Montalcino wines, then sample three different vintages paired with artisan Tuscan cheeses.

Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting

Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting

Connect with a local cook and learn how to make two staples of classic Italian cuisine with this cooking class hosted in a local's kitchen. Discover the secrets to turning out flawless fresh pasta with two different recipes for both a stuffed and a shaped version. Then assemble a show-stopping tiramisù from scratch under the guidance of your instructor and host. Cap off your experience by sampling your creations.

4.5

from $47

Cesarine: Small group Pasta and Tiramisu class in Siena

Cesarine: Small group Pasta and Tiramisu class in Siena

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).

(22)

from $211

Secret Siena Walking Tour

Explore the mysterious, magical world of truffles, wander through the woods in the company of a local expert truffle hunter and his dogs and enjoy a unique and direct experience of this ancient tradition. Truffles are a seasonal delicacy but in this area we are very lucky, in spring we can find the Marzuolo or March truffle, in summer the Tartufo Nero Scorzone, a black Summer truffle, while in winter there are black winter truffles but also sometimes the famous " Bianco delle Crete Senesi", the highly prized white truffle. Outside our farm house we meet up with our expert truffle hunter and his wonderful dogs. To help you get the best of the companionship of the truffle hunter, a mine of information on truffles, the dogs, the woods and countryside and the local area in general you will be accompanied by an English speaking interpreter - generally an interpreter who also assists in the cooking classes and so able to give you tips on storing and using the truffles in the kitchen.

(11)

from $265

Per group

Truffle Hunting in Tuscany

Explore Siena’s historical highlights and iconic cathedral on a private walking tour of the historic center. This short but comprehensive tour is designed for curious travelers who want to maximize their limited time in this Tuscan city. As you admire Piazza San Domenico, Torre del Mangia, and other local treasures, your guide will provide illuminating commentary that takes you out of the guidebook and into medieval Tuscany.

4.7

(43)

from $124

Siena Private Walking Tour: Traditions, Streets & Cathedral

Siena Private Walking Tour: Traditions, Streets & Cathedral

2 to 3 hoursFree Cancellation

4.5

(81)

from $182

Begin your adventure with a friendly introduction by professional staff who ensure you feel comfortable and confident before setting off. Once in the saddle, ride through lush vineyards, olive groves, native woodlands, and scenic hills, soaking in breathtaking panoramic views that define the Tuscan landscape. Enjoy a relaxing and immersive journey far from the crowds, surrounded by nature, tradition, and timeless beauty. This Chianti horseback riding experience is the perfect way to explore Tuscany at a slow pace and create unforgettable memories in the countryside.

Likely to Sell Out

Chianti Horseback Riding Tour at San Gimignano

Chianti Horseback Riding Tour at San Gimignano

1 hour 30 minutesFree Cancellation

4.0

from $100

Discover UNESCO-listed Siena through the eyes of a local on this custom-made Lokafy walking tour. Skip the typical guided tour and instead connect with a Siena local who will show you around their city like a friend and introduce you to the neighborhoods that they know and love. As you explore the city, gain an insight into Tuscan culture, cuisine, and everyday life; and receive recommendations on where to eat, drink, and shop.

Siena Private Walking Tour with a Local

2 to 6 hoursFree Cancellation

4.3

(15)

from $57

Immerse yourself in the culinary traditions of Siena during a small-group cooking class set in a charming historical villa. Discover the secrets of Tuscan cuisine and learn to prepare authentic Italian dishes, including ravioli and tiramisu, under the guidance of a skilled chef. After, indulge in a wine tasting, savoring the flavors of local wineries. Finally, tour the villa and admire its rustic charm and surroundings.

Likely to Sell Out

Cooking Class in a historical Palace in Siena Provence

Cooking Class in a historical Palace in Siena Provence

Optimize your travel time with this private transfer that breaks up the trip from Siena to Rome with stops in Orvieto and Civita di Bagnoregio to sightsee, shop, and dine. Enjoy hassle-free pickup at your hotel or other accommodation in Siena and enjoy views of the Tuscan countryside as you head south. Stop for free time to explore Orvieto and Civita before drop-off at your final destination in Rome.

(43)

from $138

Siena to Rome: Orvieto and Montepulciano Transfer Tour

Siena to Rome: Orvieto and Montepulciano Transfer Tour

7 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!

(3)

from $1,168

Per group

Siena Tour and exclusive window on Piazza del Campo

Siena Tour and exclusive window on Piazza del Campo

(41)

from $206

Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

8 hoursFree Cancellation

⭐ Experience Highlights — What’s Included Visit to Our Historic Wine Estate- Discover an organic winery with over 300 years of heritage. ️ Chef-Prepared Three-Course Lunch - Featuring the truffles you found with fresh caprese salad, pasta, dessert, or cheese selections Truffle & Wine Pairing- Guided tasting of three organic estate wines selected by our chef & Sommelier. Free Time to Explore the Vineyards - Enjoy breathtaking views overlooking Siena.

(107)

from $270

Wine Tour & Tasting Lunch

Immerse yourself in the Tuscan countryside on a small-group ATV excursion. Select a start time that works for you and get a briefing from your guide. Test out the ATV until you feel comfortable. Then, enjoy the adrenaline rush as you discover the UNESCO-listed Crete Senesi area from Chianti to Val d’Orcia by ATV. Your guide is on hand at all times to offer assistance or answer questions.

(11)

from $71

Exciting ATV tour in the Tuscan countryside

Exciting ATV tour in the Tuscan countryside

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.

(39)

from $228

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

4.7

(16)

from $295

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

(23)

from $393

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

Honeymoon wine tour in Montepulciano! We made something special for them!

6 to 8 hoursFree Cancellation

Get up close and personal with Tuscany’s ineffable scenery, and explore with ease, on a full-day tour by electric bike. Meet your guide in Siena, get familiar with your bike and helmet, and head into the Chianti Hills. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local farm/winery, where you can enjoy a traditional meal and generous wine tasting.

(80)

from $294

Small Group E-Bike Chianti Tour with farm lunch from Siena

Small Group E-Bike Chianti Tour with farm lunch from Siena

6 hoursFree Cancellation

Chianti Classico E-Bike Tour

(37)

from $224

5 to 6 hoursFree Cancellation

(25)

from $307

Explore the enchanting Chianti region during your trip from Siena to Florence with our expert local driver, aboard a comfortable Minivan with a large trunk. Immerse yourself in the picturesque Tuscan landscape adorned with rolling hills, vineyards, cypresses, olive trees, and sunflowers. Itinerary: • Private collection at the indicated address. • 1st stop at the Monteriggioni Castle, an invincible castle and ancient outpost built by the Republic of Siena, serving as a strategic control point along the historic Via Francigena (the medieval road once traveled by Crusader soldiers and pilgrims). • 2nd stop in San Gimignano, a true open-air museum, famous worldwide for its valuable medieval towers and typical shops managed by expert craftsmen. If you wish, you can ask our driver to make an additional stop in the cellar to enjoy a typical lunch or a fine wine tasting, with an additional cost based on the extended time. This is our beautiful Tuscany for you !

PRIVATE TRANSFER from Siena to Florence with stop in S Gimignano & Monteriggioni

4 hoursFree Cancellation

(3)

from $177

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

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Top Attractions in Siena

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The magnificent Gothic and Romanesque structure of Siena Cathedral (Duomo).

Attractions

What are people saying about Siena

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

Skip the Line: Siena Duomo and City Walking Tour

Carole_H, Aug 2026

Great guide for this beautiful historic city with centuries old traditions.

Leave plenty of time to get to the meeting point and to be on time. Parking appears close, but there were elevators and hills to negotiate which took a lot of time and our phone maps were not working well. The locals finally pointed us in the right direction! Our guide Guilia was wonderful! Super knowledgable, with great information about the history of Siena, the contratos, the world famous Palio racing, the architecture of Siena and the traditions of the Siennese. The tour was just about the right length (2 hours), taking in the Duomo, and the Campo main square (among other sights), and the listening devices worked well. Guilia also made recommendations of other must see places for later in the day. Would highly recommend Guilia, and the beautiful city of Siena.

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

Noelle_S, Jul 2026

Fun date night dinner

My partner and I had a lot of fun with this cooking class and it met our expectations. We enjoyed learning how to knead the pasta dough and pressing out/ cutting the shapes for tortellini, tagliatelle and ravioli. It was a heat wave in Siena and the space had adequate A/C which was definitely necessary and appreciated as A/C is impossible to find in Siena. The food tasted just "ok" at dinner but the class had maybe 14 people in it all making the pasta so I wasn't expecting perfection. If you are a serious chef, this is not the class for you, you would need a much longer experience. They pasta ingredients are already in a bowl and you mix them together, knead the dough and make the shapes. You are not really cooking as you don't make the sauce or actually see the kitchen itself. That being said, it was the perfect length and type of experience for us. Red wine was served in jugs at dinner and plentiful. Water was served during the pasta making portion. The chefs were helpful and moved around the room to make sure everyone knew what they were doing. I would recommend this for couples looking for a fun evening or families with kids.

Small-Group Tuscan Cooking Class with Wine & Lunch from Siena

Robert_P, Jul 2026

Amazing time. We...

Amazing time. We accidentally arrived 50mins early and our host didn’t mind a bit. He took my wife and I to the back yard and gave us beer from his personal supply and talked a while. The view was sensational. When everyone arrived we went into the room where the class was held. Our instructor made everyone feel relaxed and answered any questions that came up. After we made the pasta we had a small break to drink Chianti or beer and to get to know other people in the class. Then we made tiramisu. After that we had lunch which consisted of bruschetta, the pasta we made and finally the tiramisu. Can’t wait to come back and do it again!

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

Richard_B, Jul 2026

Fantastic tour

It was a really great wine tour, all 3 wineries were fantastic and the lunch was absolutely amazing. Pablo our guide was very informative and a really nice guy. We could not recommend this tour highly enough. We have done wine tours in Nappa valley and Santa Barbra before, this was our first in Italy 🇮🇹 and it was up there with the best. (Ps we are not American)

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

Zoe_N, Jul 2026

Wonderful Surprise!

Experiencing a long table for lunch with new found friends while tasting several wines & eating authentic Italian food was much more than expected. I even bought Biscotti & Pasta! Discovering Siena on foot, seeing the Cathedral & revisiting the history & learning the culture of the city is priceless!

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Natalie_M, Jun 2026

A sensational evening to be had!

This experience was a highlight of our trip to Siena. Helene hosted our vineyard tour and chef-prepared, delicious 4 course dinner with generous paired wine tastings in excellent English, making the experience easy and very relaxed. The vineyard was easy to find and such a stunning and picturesque location, we felt we got great value for money and highly recommend.

Small-Group San Gimignano and Volterra Day Trip from Siena

Robert_T, Jun 2026

Tuscan Escapes - San Gimignano and Volterra

Ceco was an amazing guide for the day. The right amount of interesting history and facts delivered with passion and interest, balanced with sufficient time for self-exploration. Comfortable and safe vehicle to travel in. Small group made this souch more enjoyable and accessible. The lunch at Carmela's property was superb and just added to an already great day. Highly recommend Tuscan Escapes for the care they take and the passion they have for the Tuscan region (as evidenced by the high quality of their guides).

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.

Small-Group Montepulciano and Pienza Day Trip from Siena

Jennifer_H, Jun 2026

Our time in Montepulciano...

Our time in Montepulciano was one of our favorite days in Italy. Giovanni was an exceptional guide and he taught us so much about the wine and the area. We highly recommend Tuscan Wine Tours as they book small wineries. Our delicious lunch was at a dairy farm where we overlooked the gorgeous Tuscan region.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Desmond_R, May 2026

Awesome experience

It is a small bit of everything you'd want to experience at a vineyard ☺️. The guide and her team are friendly, helpful and happy that you are their guests. We enjoyed the small tour of history and the 3-course meal was a light delight. The wines were delicious 😋. Lovely experience for the price at hand.👌🏾

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.