All Siena Tours &amp; Excursions in 2026

Skip the Line: Siena Duomo and City Walking Tour

2 hoursFree Cancellation

4.8

(767)

from US$47

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

11 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.

(180)

from US$93

Likely to Sell Out

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.

Chianti Vespa Tour

4 hoursFree Cancellation

4.0

(9)

from US$128

From Siena Best of Tuscany Wines and Lunch in Montepulciano

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 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.

(11)

from US$116

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

1 hour 30 minutesFree Cancellation

4.7

(117)

from US$69

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

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

9 hoursFree Cancellation

4.9

(1,011)

from US$223

Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

2 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.

(2)

from US$82

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Horsebackriding - explore Tuscan nature

(49)

from US$111

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.

4.7

(31)

from US$100

Siena : Siena Guided Tour with Duomo or Museum

1 hourFree Cancellation

4.3

(44)

from US$41

Siena Walking Tour with Audio and Written Guide by a local

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the support of a local, you will be able to visit all the most important monuments at your own pace: Piazza del Campo, the Duomo, Basilica di San Domenico and much more! You'll get to know the stories and curiosities of Siena! But also you will discover everything about local foods, Italian aperitivo in authentic local restaurants, and much more! What are you waiting for?

Siena Walking Tour with Audio and Written Guide by a local

4 to 5 hoursFree Cancellation

4.4

(41)

from US$7

Price varies by group size

Likely to Sell Out

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

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

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.

4.9

(232)

from US$86

Special Offer

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

10 to 11 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

4.8

(260)

from US$182

Price varies by group size

Siena: A Wine Tour and Tasting Experience

Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

(391)

from US$100

Likely to Sell Out

San Gimignano, Chianti, and Montalcino Day Trip from Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena

11 hoursFree Cancellation

4.3

(151)

from US$164

Special Offer

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

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

4.9

(317)

from US$223

Siena Underground Wine tasting in a Medieval Cave

1 hourFree Cancellation

Hidden Castles & Chianti Wine Experience– Small Group

(60)

from US$88

5 hoursFree Cancellation

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.

(179)

from US$57

Guided Winery Tour and Wine Tasting in Siena

2 hours 30 minutesFree Cancellation

A Brunello Cooking Class with Vineyards View Winery

(72)

from US$88

Special Offer

Cooking Class in a Tuscan Castle Brunello Winery

4 hoursFree Cancellation

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti’s rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

Chianti Half Day Wine Tasting Tour from Siena

5 hoursFree Cancellation

Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.

(11)

from US$57

Tuscany 2-Days 5-Cities Flexible Sightseeing bus tour

Tuscany 2-Days 5-Cities Flexible Sightseeing bus tour

2 daysFree Cancellation

Siena: A Wine Tour and Tasting Experience

(4)

from US$73

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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

Amy_O, Jul 2026

A gorgeous afternoon in the Tuscan countryside

We really enjoyed this tour of the gorgeous La Lastra vineyard! Lorenzo was a great guide - knowledgeable and fun! The main house was beautiful and meeting one of their lovely little cats was an added bonus. The lunch served was delicious, and they asked about dietary requirements beforehand which was great as my partner and I are vegetarian. The tour was the perfect mix of laidback, low pressure and genuinely really interesting. You should definitely go here if you’re visiting Siena!!!

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!

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

Sarah_G, Jul 2026

Wonderful day trip, lunch and wine tasting

The tour was wonderful, we loved San Gimignano with its amazing towers. We had our own free time to explore all the stops. Our guide Ricardo was excellent. He gave us lots of interesting information on the places we were visiting and made sure we all knew the time and place we were meeting. He guided us through Sienna. The wine tasting was fabulous, we tasted 4 glasses of wine , 2 Spumante. The food was great. This is an 11 hour trip but it was only a little walking. We loved it. Christina helped Ricardo with the tour. It was really good value for money and I highly recommended doing it. Bellissimo!

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

SANYA_R, Jul 2026

The most amazing experience ever!

We had an amazing time in this class and learned so much! From the moment we arrived, the staff and instructors made us feel so welcome, creating a fun and relaxed atmosphere. The time flew by while we were making the pasta, and the wait for it to be cooked was absolutely worth it because it was hands down the best pasta we've ever had! We got to make three different types of pasta, and our favorite was the tagliatelle, so be sure to save room for that... and for the delicious tiramisu at the end. This was one of the highlights of our time in Siena, and we couldn't recommend it more. 100000% recommended!

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)

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.

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.👌🏾

Hidden Castles & Chianti Wine Experience– Small Group

Jeremy_P, Oct 2025

Tour host was extremly...

Tour host was extremly knowledgeable and created a friendly atmosphere on the mini-bus. The 2 wine tasting experiences were excellent, but contrasting. One being more of a family vine yard located on an old Tuscan farm in the hills, the other being a dedicated tasting / function venue, hosted by a charismatic Sommelier. Quality of wine superb and from my hazy memory exceeded the 7 glasses advertised! Only down side was disorganised pick-up at station. Having a wine tour notice on bus and having host there at stated meet time, 15 mins before departure. Italian speaking driver turned several clients away before host arrived. Still a 5-Star tour though, as rest of afternoon made up for this.