All Siena Tours &amp; Excursions in 2026

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 hoursFree Cancellation

4.0

(14)

from $117

Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

2 hoursFree Cancellation

(2)

from $83

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.

If you've only got limited time in Siena, make sure you maximize your experience of the Tuscan hot spot on a sightseeing tour that includes skip-the-line entry. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo and stroll the streets with your guide, learning about the history of the place and leaving the navigating to someone else. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket.

Chianti Vespa Tour

4 hoursFree Cancellation

4.1

(10)

from $130

Skip the Line: Siena Duomo and City Walking Tour

2 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.

(773)

from $48

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

(121)

from $70

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

(262)

from $185

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.

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Get views you can't find anywhere else on this hot-air balloon ride over Tuscany. Starting in Siena, float above the countryside and take in scenic views of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) and enjoy seeing the countryside and surrounding ancient villages and towns. Upon landing, enjoy a glass of sparkling wine to celebrate your experience.

(49)

from $113

Hot Air Balloon Flight Over Tuscany from Siena

Hot Air Balloon Flight Over Tuscany from Siena

(144)

from $369

What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci, a family winery surrounded by the rolling hills of Montalcino. Guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the traditions, craftsmanship and passion behind Brunello di Montalcino production. The experience continues with a carefully curated tasting of premium Tuscan wines paired with a traditional Tuscan lunch featuring local specialities and fresh handmade pasta, creating a journey that combines wine, food and landscape in a truly authentic way. Far from crowded commercial tours, this immersive experience offers a refined and memorable taste of Tuscany in a relaxed and elegant setting. Each tasting is led by expert sommeliers, transforming every glass into a deeper journey through the world of Brunello di Montalcino.

Montalcino: Brunello Wine Tasting & Tuscan Lunch

Montalcino: Brunello Wine Tasting & Tuscan Lunch

1 hour 30 minutesFree Cancellation

(10)

from $117

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.

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 $167

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

(1,015)

from $226

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

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

Siena: A Wine Tour and Tasting Experience

(236)

from $87

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.

(391)

from $101

Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

Siena: Pasta and Tiramisu Small Group Cooking Class with Wine

(320)

from $226

Special Offer

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

(42)

from $7

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.

Siena : Siena Guided Tour with Duomo or Museum

1 hourFree Cancellation

4.3

(45)

from $42

Classic Wine Tasting with Traditional Tuscan Products

There are places you visit and others you live. A few minutes from Siena, between the Chianti hills and the Crete Senesi, the experience slowly takes shape on our panoramic terrace, in the shade of an ancient white mulberry tree. What makes it special is the opportunity to taste our wines directly with those who produce them, in a family-run cellar where each bottle is born from the link with the territory. It is not a standard tasting, but an authentic moment made of stories, flavors and genuine hospitality. The wines tell the story of the territory, the typical Tuscan dishes accompany them and the landscape completes the experience. If you are looking for a real meeting with Tuscany, made of details, hospitality and dedicated time, this is the right place.

Classic Wine Tasting with Traditional Tuscan Products

1 hour 30 minutesFree Cancellation

A Brunello Cooking Class with Vineyards View Winery

(78)

from $33

Special Offer

Cooking Class in a Tuscan Castle Brunello Winery

4 hoursFree Cancellation

Special Offer

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.

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

10 to 11 hoursFree Cancellation

Indulge in Siena's culinary treasures on a private tour designed to delight your palate, led by an expert local guide. Stroll through charming cobblestone streets, where the enticing aromas from bustling food stalls beckon. Begin your epicurean journey with the crispy perfection of coccoli, drizzled with aromatic olive oil, and savor the multi-layered flavors of savory panini, each bite a testament to Siena's rich gastronomic heritage. As you meander through the city, your guide will share enthralling tales of Siena's history, blending tradition with modern culinary innovations. Discover how the city's vibrant food scene reflects its cultural tapestry, making this tour an ideal exploration for devoted foodies and curious travelers alike. Each stop unveils a new chapter in Siena's epicurean story, promising a memorable adventure that intertwines taste and tradition in the heart of this historic city.

Best Siena Street Food Tour With 4+ Tastings

(10)

from $101

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan with an English-speaking driver and complimentary water. Small group experience, maximum 8 participants. Please note that from November to April, and in case of bad weather, lunch will take place indoors. For tours departing on Mondays, lunch is always served in an indoor restaurant. Why choose us? • Guaranteed departures • Secure booking • 24-hour cancellation policy • Best rates guaranteed For operational reasons, the itinerary order may vary between Montepulciano and Montalcino.

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

4.6

(5)

from $273

Visit San Gimignano and Volterra the easy way from Siena, on an intimate small-grop tour. Head to the hilltop town of Monteriggioni, then stop for a while in UNESCO World Heritage–listed San Gimignano, with its medieval towers and views over the Tuscan countryside. Drop into an alabaster workshop in Volterra, then indulge in a rustic lunch at a Tuscan farm. Learn about local history and culture along the way.

Small-Group San Gimignano and Volterra Day Trip from Siena

8 hoursFree Cancellation

Skip the Line: Siena Duomo and City Walking Tour

(200)

from $226

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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

Adrian_S, Aug 2026

One of the best walking tours we've done

Elio was brilliant - friendly, engaging and incredibly knowledgable about the city, the art and the culture. We've done a lot of these sorts of tours in different places and he is one of the best guides we've had. He said he also does tours in Florence and we will definitely book with him next time we are there. Thank you so much Elio!

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

Aidan_F, Aug 2026

Day trip in Tuscany

This was such a fun day trip through the Tuscan region, with wine tasting, a delicious lunch, and plenty of beautiful scenery along the way. The highlight for me was definitely spending the afternoon exploring Siena. A great way to experience the best of Tuscany in one day!

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

Leahnna_M, Jul 2026

Wonderful day in Montalcino

We had a wonderful time exploring 3 different vineyards in Montalcino, where we were warmly welcomed at each. Marco, our tour guide was knowledgeable and so much fun! By the end of the day I felt like he was our friend. We enjoyed a lovely lunch at the second vineyard, Cava D’Onice with the wine maker Simone in his home, made by his wife (The Big Boss as Simone calls her!) Marco took time to take us to an 11th century Abbey to explore, which was stunning! I highly recommend this tour, with any luck you’ll have Marco as your guide!

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.

Siena: Chianti Sunset Tour with Dinner & Wine Tasting

Aidan_F, Jul 2026

Outstanding Experience

This is a fabulous tour / Al a Carte experience. The tour of the vineyard gave a great insight into the history of the Chianti region and the importance of the grapes. The best was yet to come, they have an outstanding Chef who created a four course meal to accompany four of the wines produced there, the meal was incredible served on the terrace over looking the vines as the sun set. The team looking after us, some of which are the owners, we're such great hosts, this is a must visit to experience. Aidan & Becky

Siena: A Wine Tour and Tasting Experience

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

Steve_C, Jul 2026

Highlight of our trip

One of the best highlights of our trip. Simone was welcoming and personable. His instructions were easy to follow and our final recipes were delicious. I would highly recommend this class to anyone traveling to Siena. Best ravioli with truffles and tirimisu. Can't wait to practice at home.

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.👌🏾

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!!

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.

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.