Tours and activities in Siena, Italy

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Tours and activities in Siena, Italy | SimilarTours

Skip-the-line tickets in Siena

Major attractions with reserved entry - skip the queue, walk straight in

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Headout
Siena Cathedral & Piccolomini Library Tickets with Audio Guide
Discover the artistic heart of Siena with access to its most iconic treasures.
4.3(3755)
Siena, Italy
Free cancellation
Instant confirmation
EnglishSpanishFrench+13
From
$14
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© Di Rasto SK
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Siena Cathedral Complex (Opa Si Pass)
Explore faith through culture and art in the magnificent complex of the Cathedral of Siena. With a pass you can choose what you'd like to see most, from the crypt to the Opera Museum.
4.5(920)
Siena, Italy
Instant confirmation
EnglishFrenchGerman+2
From
$25
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Viator
Wine Class - Tuscan Classics
Are you a curious and thirsty traveler looking to uncork some of Tuscany's wine secrets? Come to the Tuscan Wine School for an informative and fun class to learn about Tuscany's most important, traditional wines led by an English-speaking local expert. Discover the history and legends behind Tuscany's most significant wines and learn to swirl, smell and sip your way through the different types and styles of wine. The tasting of wines is enhanced by a series of different sample foods, and food pairing tips will be discussed, leaving you able to make better choices when choosing from local names in the city's restaurants.
4.9(266)
2 hours
Siena, Italy
Free cancellation
English
From
$71
No similar experiences found
Musement
Florence Duomo Cathedral guided tour with skip-the-line ticket from Siena
Explore the city on foot with a knowledgeable guide. Visit its most iconic landmarks, from grand piazzas to famous bridges and cathedrals.
7 hr 40 min
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$87
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Headout
Siena Cathedral Complex OPA SI Pass with Audio Guide
Enjoy three-day access to Siena’s Cathedral complex, including the Duomo, Baptistery, Crypt, and more, with a digital audio guide.
4.4(2202)
Siena, Italy
Free cancellation
EnglishSpanishFrench+13
From
$28
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© partner
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Siena Synagogue: Entry Ticket
The Synagogue of Siena, located only a few steps from the Piazza del Campo, stands in the heart of the ancient Jewish Ghetto of Siena, where Sienese Jews remained confined until 1859.
3.4(17)
Siena, Italy
Instant confirmation
PortugueseChineseSpanish+14
From
$8
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Viator
Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better
Siena is one of Tuscany's best-loved cities, a fixed stop for those in the Chianti region. A destination for many visitors, Siena is internationally known not only for its picturesque, medieval historical centre, the famous Palio di Siena in Piazza del Campo and the colourful countryside that surrounds it, but also for the delicious cuisine it offers. It is impossible not to think of the excellent dishes and exquisite wines that can be found in the city. Thanks to our gastronomic tour of Siena, we will discover together the secret dishes and recipes of the Sienese tradition.
4.9(239)
3 hours
Siena, Italy
Free cancellation
EnglishItalian
From
$86
No similar experiences found
Musement
Chianti half-day tour from Siena with wine and olive oil tastings
Explore Chianti's rolling hills on a half-day tour from Siena. Visit charming Castellina, enjoy guided wine tastings and sample local olive oil.
5 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$58
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Headout

Siena Cathedral & Piccolomini Library Tickets with Audio Guide

4.3(3755)

Siena, Italy

Free cancellation
Instant confirmation

From

$14

Tiqets

Siena Cathedral Complex (Opa Si Pass)

4.5(920)

Siena, Italy

Instant confirmation

From

$25

Viator

Wine Class - Tuscan Classics

4.9(266)

2 hours

Siena, Italy

Free cancellation

From

$71

Musement

Florence Duomo Cathedral guided tour with skip-the-line ticket from Siena

7 hr 40 min

Siena, Italy

Free cancellation
Instant confirmation

From

$87

Headout

Siena Cathedral Complex OPA SI Pass with Audio Guide

4.4(2202)

Siena, Italy

Free cancellation

From

$28

Tiqets

Siena Synagogue: Entry Ticket

3.4(17)

Siena, Italy

Instant confirmation

From

Viator

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

4.9(239)

3 hours

Siena, Italy

Free cancellation

From

$86

Musement

Chianti half-day tour from Siena with wine and olive oil tastings

5 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$58

Guided walking tours in Siena

Small-group + private walking tours with a local guide

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Musement
Opa Si Pass: access to Siena Cathedral complex
Buy your Opa Si Pass to the Siena Cathedral complex: visit the Crypt, the Baptistery and the Museum saving 50% on the total of single admissions!
4.6(541)
3 days
Siena, Italy
Free cancellation
Instant confirmation
From
$24
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Viator
Skip the Line: Siena Duomo and City Walking Tour
Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and visit the stunning Siena Duomo (Siena Cathedral) with your fast-track, skip-the-line entrance ticket. As you walk through this incredibly beautiful Tuscan city with your expert guide, you'll feel as though you’ve journeyed back in time.
4.8(780)
2 hours
Siena, Italy
Free cancellation
English
From
$47
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Headout
Small-Group Guided Tour of Siena with Optional Cathedral Entry
Experience Siena through the eyes of a local, as a professional guide takes you on an exciting walking tour. See the magnificent Siena Cathedral, Palazzo Pubblico, and Piazza del Campo in the flesh!
4.4(1163)
1 hour
Siena, Italy
Free cancellation
EnglishSpanishFrench+13
From
$34
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© Opera Laboratori Fiorentini
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Siena Cathedral: Skip The Line Ticket + Guided Tour
See one of Italy’s most unique treasures with a tour of the Siena Cathedral. Enjoy skip-the-line entry and a guided tour of the marble floor.
4.0(3)
1 hr 10 min
Siena, Italy
Instant confirmation
EnglishItalian
From
$35
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Musement
Entry ticket to Siena Civic Museum at Palazzo Pubblico
Dive into Siena's history with access to the Civic Museum at Palazzo Pubblico. Discover exquisite art and Gothic architecture.
Siena, Italy
Instant confirmation
From
$16
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Viator
Hidden Castles & Chianti Wine Experience– Small Group
Visit two charming family-run wineries in the heart of the Chianti region, learn about local winemaking traditions, and taste 7 exquisite wines paired with bruschetta, salami, cheese, and extra virgin olive oil. Between tastings, stop at the medieval village of Monteriggioni for free time to explore or relax before returning comfortably to Siena. travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people. Note :Wine tastings take place in English, with your tour leader providing translation support when needed. A moderate amount of stairs and walking is involved During special events, opening times can change The tour itinerary may change, but all tour stops will be visited
4.5(181)
5 hours
Siena, Italy
Free cancellation
Likely to sell out
EnglishItalianSpanish
From
$58
No similar experiences found
Headout
Siena Cathedral & Piccolomini Library Guided Tour
Step inside Siena Cathedral and experience one of Italy’s rarest artistic treasures: its spectacular marble floor, revealed to visitors only during a limited period each year.
5.0(1)
1 hour
Siena, Italy
EnglishSpanishFrench+13
From
$35
© Opera Laboratori Fiorentini
Tiqets
Siena: Guided Walking Tour + Siena Cathedral & Palazzo delle Papesse Entry
Join a guided walk through Siena and visit important landmarks of the city.
0.0(0)
1 hr 10 min
Siena, Italy
Instant confirmation
EnglishItalian
From
$49
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Musement

Opa Si Pass: access to Siena Cathedral complex

4.6(541)

3 days

Siena, Italy

Free cancellation
Instant confirmation

From

$24

Viator

Skip the Line: Siena Duomo and City Walking Tour

4.8(780)

2 hours

Siena, Italy

Free cancellation

From

$47

Headout

Small-Group Guided Tour of Siena with Optional Cathedral Entry

4.4(1163)

1 hour

Siena, Italy

Free cancellation

From

$34

Tiqets

Siena Cathedral: Skip The Line Ticket + Guided Tour

4.0(3)

1 hr 10 min

Siena, Italy

Instant confirmation

From

$35

Musement

Entry ticket to Siena Civic Museum at Palazzo Pubblico

Siena, Italy

Instant confirmation

From

$16

Viator

Hidden Castles & Chianti Wine Experience– Small Group

4.5(181)

5 hours

Siena, Italy

Free cancellation
Likely to sell out

From

$58

Headout

Siena Cathedral & Piccolomini Library Guided Tour

5.0(1)

1 hour

Siena, Italy

From

$35

Tiqets

Siena: Guided Walking Tour + Siena Cathedral & Palazzo delle Papesse Entry

0.0(0)

1 hr 10 min

Siena, Italy

Instant confirmation

From

$49

Food & drink experiences in Siena

Food tours, market walks, wine tastings, cocktail experiences

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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover the cellars where these incredible wines age, meet the local producers, and learn about the passion that goes into making this wine. Enjoy a traditional Tuscan lunch at a winery and spend time relaxing at your leisure in the village of Montalcino before exploring the mystical abbey of Sant'Antimo. Visit a total of three wineries in the region, tasting unique creations at each one. Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.
4.9(1017)
9 hours
Siena, Italy
Free cancellation
English
From
$225
No similar experiences found
Musement
Chianti Winery Tour from Siena with Tasting and Food
Enjoy this Chianti tour from Siena with wine tasting. Visit two wineries and small villages, and sample typical Tuscan products.
4.0(1)
5 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$100
No similar experiences found
© Do Eat Better
Tiqets
Siena: Food and Wine Tasting Tour
Step right into the heart of Siena and embark on a delightful food tour that will tantalize your taste buds.
5.0(1)
3 hr 30 min
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalian
From
$99
No similar experiences found
Viator
Siena: A Wine Tour and Tasting Experience
In the hills of the gorgeous Tuscan countryside, just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine and Life' is a 3-hour tour held in an organic winery. Learn about the different stages of wine making through the seasons and enjoy tastings and a light lunch.
5.0(391)
3 hours
Siena, Italy
Free cancellation
EnglishItalian
From
$101
No similar experiences found
Musement
Wine tasting and lunch in a typical winery in Montepulciano
Visit the underground of a cellar from the XVI century in Montalcino, taste local wine and snacks and enjoy a typical Tuscan lunch.
4.0(1)
1 hr 30 min
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalian
From
$65
No similar experiences found
© myTour in Italy
Tiqets
Montalcino: Wine Tasting Tour from San Gimignano
Taste the masterful craftsmanship hidden within each bottle of Brunello, the world's most adored wine, and the esteemed "Italian ambassador" in the realm of winemaking.
0.0(0)
6 hr 30 min
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$138
No similar experiences found
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Educational guided wine tour and tasting in Siena
Enjoy a tour of the winery, taste local wines and a light lunch and learn all you need to know about wine production.
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalian
From
$100
No similar experiences found
Musement
Taste Siena Food and Wine in a Small Group Guided Tour
Join an unforgettable tasting tour in the city. Savour local wines, olive oil, cheeses, and traditional foods under expert guidance.
2 hours
Siena, Italy
Free cancellation
Instant confirmation
English
From
$71
No similar experiences found

Viator

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

4.9(1017)

9 hours

Siena, Italy

Free cancellation

From

$225

Musement

Chianti Winery Tour from Siena with Tasting and Food

4.0(1)

5 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$100

Tiqets

Siena: Food and Wine Tasting Tour

5.0(1)

3 hr 30 min

Siena, Italy

Free cancellation
Instant confirmation

From

$99

Viator

Siena: A Wine Tour and Tasting Experience

5.0(391)

3 hours

Siena, Italy

Free cancellation

From

$101

Musement

Wine tasting and lunch in a typical winery in Montepulciano

4.0(1)

1 hr 30 min

Siena, Italy

Free cancellation
Instant confirmation

From

$65

Tiqets

Montalcino: Wine Tasting Tour from San Gimignano

0.0(0)

6 hr 30 min

Siena, Italy

Free cancellation
Instant confirmation

From

$138

Musement

Educational guided wine tour and tasting in Siena

Siena, Italy

Free cancellation
Instant confirmation

From

$100

Musement

Taste Siena Food and Wine in a Small Group Guided Tour

2 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$71

Cooking classes & workshops in Siena

Hands-on classes - pasta, pizza, gelato, regional dishes - from local chefs

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Viator
Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner
Tuscan Cooking Class. Cooking Class of a traditional Tuscan meal from starter to dessert including a fresh local handmade pasta. At the end of the lesson dinner is served with what we have prepared during the class, accompanied with local Tuscan red Wine. The maximum number of customers per lesson is 15 people. The minimum number of participants required for the lesson is 4. Customers actively participate in the preparation of recipes. Use of seasonal and local ingredients. Vegetarian and gluten-free menus available. Customers will learn all the secrets of Italian and Tuscan cuisine and will receive handouts with the prepared recipes. Private lessons on request in the morning at 10 AM.
4.8(353)
4 hours
Siena, Italy
Free cancellation
EnglishItalian
From
$154
No similar experiences found
Headout
Siena Pasta and Tiramisu Cooking Class
Master Tuscan pasta and tiramisu from scratch in a small-group cooking class led by a local chef in Siena.
4.5(2)
3 hours
Siena, Italy
Free cancellation
EnglishSpanishFrench+13
From
$80
No similar experiences found
© MY TOUR - MY RENT S.R.L.
Tiqets
Siena: Pizza & Gelato Cooking Class + Dinner + Drinks
Join a 4-hour cooking class at a Chianti farm. Follow a professional chef to make authentic pizza from scratch and craft gelato.
0.0(0)
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalian
From
$133
No similar experiences found
Musement
Market tour and dining experience at a Cesarina's home in Siena
Visit Siena's vibrant local market and immerse yourself in a private dining experience at a Cesarina's home!
4 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalian
From
$164
No similar experiences found
Viator
A Brunello Cooking Class with Vineyards View Winery
Brunello Cooking Class with Chef Alexandra - Cooking class with a view in the morning, followed by Lunch pairing with Brunello wines! With the guidance of our chef Alexandra, you will learn to make classic Tuscan dishes using the finest local delicacies, after which you will enjoy a private tour of the vineyards and the XV century castle that’s been in the family for 17 generations. Enjoy the lunch you prepared yourself on our panoramic terrace overlooking the rolling hills of Montalcino wine country. Each dish will be expertly paired with our own wine production. Tour Length: 4 hours ( Class + Lunch ) - Every day Departure Point: Possible add-on we can organize for you PICK-UP DROP OFF IN THE PROVINCE OF SIENA Meeting time: 10.00 am Popularity: (best seller wine and food tour in Tuscany) INCLUDED: All Included ( Cooking lesson, Tours, Tasting Lunch, Extra optional Transportation from and to the cooking venue )
5.0(313)
4 hours
Siena, Italy
Free cancellation
EnglishItalian
From
$306
No similar experiences found
© MY TOUR - MY RENT S.R.L.
Tiqets
Chianti: Guided Cooking Class & Wine Tasting in a Farm
Join a cooking class and wine tasting at a Chianti farm in Tuscany. Learn to prepare traditional Italian dishes and taste Chianti Classic wines.
0.0(0)
4 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalian
From
$161
No similar experiences found
Musement
Cooking Class and Wine Tasting in Chianti Farm
Discover Tuscany's gastronomic legacy with a cooking class and wine tasting experience in Chianti, learn, cook, taste, and bond over food and wine.
4 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalian
From
$164
No similar experiences found
Viator
Siena Pasta & Tiramisu Cooking Class With Wine by Cooking Italy
Learn how to make pasta and tiramisu in a popular Siena restaurant. Enjoy a glass of Prosecco upon arrival, and a glass of wine with your meal.
4.7(158)
3 hours
Siena, Italy
Free cancellation
English
From
$85
No similar experiences found

Viator

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

4.8(353)

4 hours

Siena, Italy

Free cancellation

From

$154

Headout

Siena Pasta and Tiramisu Cooking Class

4.5(2)

3 hours

Siena, Italy

Free cancellation

From

$80

Tiqets

Siena: Pizza & Gelato Cooking Class + Dinner + Drinks

0.0(0)

Siena, Italy

Free cancellation
Instant confirmation

From

$133

Musement

Market tour and dining experience at a Cesarina's home in Siena

4 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$164

Viator

A Brunello Cooking Class with Vineyards View Winery

5.0(313)

4 hours

Siena, Italy

Free cancellation

From

$306

Tiqets

Chianti: Guided Cooking Class & Wine Tasting in a Farm

0.0(0)

4 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$161

Musement

Cooking Class and Wine Tasting in Chianti Farm

4 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$164

Viator

Siena Pasta & Tiramisu Cooking Class With Wine by Cooking Italy

4.7(158)

3 hours

Siena, Italy

Free cancellation

From

$85

Cultural & historical in Siena

Museums, ruins, art collections, religious sites with expert guides

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Tiqets
Siena Cathedral & Piccolomini Library: Entry Ticket
Enter one of Italy's most important Roman-Gothic style buildings - the magical Cathedral of Siena - and marvel at the frescoes by Donatello, Michelangelo, and Pinturicchio.
4.5(1056)
Siena, Italy
Instant confirmation
EnglishFrenchGerman+2
From
$17
No similar experiences found
Musement
Entrance tickets to Siena Cathedral and Piccolomini Library
Secure your skip-the-line tickets to Siena Cathedral and Piccolomini Library. On selected dates, admire the wonderful floor of the cathedral.
4.5(108)
Siena, Italy
Free cancellation
Instant confirmation
From
$12
No similar experiences found
Headout
Siena Icons: Cathedral, Piccolomini Library and Papesse Palace Pass
The Siena Icons Pass offers you a convenient way to explore the city's most stunning attractions over three days.
4.2(21)
Siena, Italy
Free cancellation
EnglishSpanishFrench+13
From
$22
No similar experiences found
Viator
San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore the UNESCO historic center of San Gimignano at your own pace; step inside Monteriggioni’s perfectly preserved fortress. Follow the scenic Chiantigiana road to a cozy winery for a guided tasting of 3 Chianti wines and a zero-mile, 3-course lunch, finishing with cantucci & vin santo. Enjoy free time in Siena to wander Gothic lanes, browse artisan shops, and relax in lively enotecas. Quick stops at the striped Duomo and shell-shaped Piazza del Campo, home of the Palio. Ideal for travelers seeking art, wine, and views in one effortless day—round-trip transport and tour leader included. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
4.5(192)
11 hours
Siena, Italy
Free cancellation
English
From
$93
No similar experiences found
© Wikimedia Commons
Tiqets
Palazzo Pubblico: Civic Museum Entry Ticket
Visit the Civic Museum of the Palazzo Pubblico in Siena, home to over 100 years of history. See richly frescoed halls and prestigious collections that span Sienese history and art from the early 14th century to today.
4.2(32)
1 hr 30 min
Siena, Italy
Free cancellation
Instant confirmation
EnglishCzechJapanese+14
From
$16
No similar experiences found
Musement
Santa Maria della Scala Museum Complex entance ticket
Get your tickets for the Santa Maria della Scala Complex and discover over a thousand years of history in a cultural experience that goes beyond a classic museum visit!
Siena, Italy
Instant confirmation
Skip the line
EnglishItalian
From
$14
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Headout
Tickets to 1.5-Hour Horseback Riding Experience from Siena
Discover the enchanting beauty of Tuscany's Chianti hillside on a guided horseback ride, exploring picturesque vineyards, olive groves, and hidden gems.
0.0(0)
1 hr 30 min
Siena, Italy
Free cancellation
EnglishSpanishFrench+13
From
$104
No similar experiences found
Viator
Small-Group Tuscan Cooking Class with Wine & Lunch from Siena
Join in a captivating 4-hour small group cooking class, led by a talented multi-lingual chef. Uncover the secrets behind beloved Tuscan dishes in a professional kitchen setting. Learn Tuscan cooking techniques, ingredient essentials, and the magic of local culinary artistry. From homemade pasta like pici to various bruschetta or crostini, bring a taste of Tuscany to your home table. Participants will take these recipes home, ready to recreate the flavors of Tuscany in their own kitchens. Get ready to fall in love with Tuscany through its food!
4.8(176)
4 hours
Siena, Italy
Free cancellation
EnglishItalianSpanish
From
$136
No similar experiences found

Tiqets

Siena Cathedral & Piccolomini Library: Entry Ticket

4.5(1056)

Siena, Italy

Instant confirmation

From

$17

Musement

Entrance tickets to Siena Cathedral and Piccolomini Library

4.5(108)

Siena, Italy

Free cancellation
Instant confirmation

From

$12

Headout

Siena Icons: Cathedral, Piccolomini Library and Papesse Palace Pass

4.2(21)

Siena, Italy

Free cancellation

From

$22

Viator

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

4.5(192)

11 hours

Siena, Italy

Free cancellation

From

$93

Tiqets

Palazzo Pubblico: Civic Museum Entry Ticket

4.2(32)

1 hr 30 min

Siena, Italy

Free cancellation
Instant confirmation

From

$16

Musement

Santa Maria della Scala Museum Complex entance ticket

Siena, Italy

Instant confirmation
Skip the line

From

$14

Headout

Tickets to 1.5-Hour Horseback Riding Experience from Siena

0.0(0)

1 hr 30 min

Siena, Italy

Free cancellation

From

$104

Viator

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

4.8(176)

4 hours

Siena, Italy

Free cancellation

From

$136

Outdoor & adventure in Siena

Bike tours, e-bikes, kayaking, rafting, anything outside

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Musement
Scenic E-Bike Tour in Chianti Wine Region with Lunch
Explore Tuscany's famous wine region, Chianti, on an electric bike tour. Learn about local history and viticulture while enjoying a traditional Tuscan lunch at a family-owned winery.
7 hours
Siena, Italy
Free cancellation
Instant confirmation
English
From
$224
No similar experiences found
© Authentic Italy Adventures
Tiqets
Chianti Region & San Gimignano: Guided Tour + Transfers + Lunch + Horseback Ride
Visit Tuscany’s Chianti region on this tour. Begin with a drive through the area, then proceed with a horseback ride near vineyards and olive groves.
0.0(0)
4 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalian
From
$139
No similar experiences found
Viator
Exciting ATV tour in the Tuscan countryside
Get ready to explore the untamed beauty of Tuscany on an exciting UTV adventure through Chianti and the Crete Senesi. Drive along the legendary Strada dell’Eroica, surrounded by rolling hills, vineyards, and iconic cypress-lined roads. Enjoy a scenic stop near the stunning Villa Arceno, where you can admire breathtaking views and snap unforgettable photos. The route also takes you past the historic Castello di Badia a Berardenga, a medieval gem nestled in the Tuscan countryside. Then venture into the surreal landscape of the Crete Senesi, with its dramatic clay formations and open horizons. This tour is perfect for nature lovers, thrill seekers, and anyone who wants to experience Tuscany in a truly unique way—off-road, in touch with nature, and far from the crowds.
4.9(39)
2 hours
Siena, Italy
Free cancellation
EnglishItalian
From
$228
No similar experiences found
Musement
Hike from Siena to Monteriggioni with Wine Tasting
Embark on a historic trek from Siena to Monteriggioni. Explore the fortress and savor local wines. Book now for an unforgettable adventure.
4 hours
Siena, Italy
Free cancellation
Instant confirmation
English
From
$71
No similar experiences found
Viator
Small Group E-Bike Chianti Tour with farm lunch from Siena
Follow your experienced guide on a ride through the Chianti hills on comfortable and easy to use Electric Bikes: you must have cycling experience to enjoy the itinerary of hills and Tuscany's picturesque countryside. Between rides, visit a beautiful, 13th century Castle to marvel at the medieval architecture and local crafts and products. Enjoy a farm lunch accompanied by local Chianti wines and traditional and seasonal products before the final ride back to Siena. No support vehicle is provided so you must be fit to complete the itinerary.
4.8(38)
6 hours
Siena, Italy
Free cancellation
Likely to sell out
English
From
$225
No similar experiences found
Musement
Wine Safari Poggio ai Laghi Vineyard On a Vintage Off-Road
Embark on a scenic vineyard tour in the Tuscan countryside. Learn about winemaking, and taste top-notch wines, oils, and vinegars.
2 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$253
No similar experiences found
Viator
Chianti Classico E-Bike Tour
One day bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines and beauty of the landscapes. Chianti offers a unique landscapes: gentle hills covered by vineyards and olive groves, small stone villages and farm houses. We'll start biking in the hearth of Chianti Classico, only 20 minutes from Siena, during the bike tour we will reach the Castle of Brolio, owned by the Ricasoli family since 1141, and the small villages of Villa a Sesta. We will stop then in a local winery for a Chianti wine tour and tasting. The tour includes also the lunch in local restaurant located at Castelnuovo Berardenga.
5.0(25)
5 hours - 6 hours
Siena, Italy
Free cancellation
Private tour
EnglishItalianFrench
From
$308
No similar experiences found
Viator
E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles
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.
4.7(16)
7 hr 15 min
Siena, Italy
Free cancellation
Private tour
PortugueseEnglishItalian+2
From
$296
No similar experiences found

Musement

Scenic E-Bike Tour in Chianti Wine Region with Lunch

7 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$224

Tiqets

Chianti Region & San Gimignano: Guided Tour + Transfers + Lunch + Horseback Ride

0.0(0)

4 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$139

Viator

Exciting ATV tour in the Tuscan countryside

4.9(39)

2 hours

Siena, Italy

Free cancellation

From

$228

Musement

Hike from Siena to Monteriggioni with Wine Tasting

4 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$71

Viator

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

4.8(38)

6 hours

Siena, Italy

Free cancellation
Likely to sell out

From

$225

Musement

Wine Safari Poggio ai Laghi Vineyard On a Vintage Off-Road

2 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$253

Viator

Chianti Classico E-Bike Tour

5.0(25)

5 hours - 6 hours

Siena, Italy

Free cancellation
Private tour

From

$308

Viator

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

4.7(16)

7 hr 15 min

Siena, Italy

Free cancellation
Private tour

From

$296

Day trips & excursions in Siena

Half-day to full-day trips out of the city - Pompeii, Tivoli, Tuscany, you name it

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Musement
Guided walking tour of Siena
Buy your guided walking tour of Siena now. See the main monuments and landmarks of this famous medieval city in Tuscany.
4.1(10)
1 hour
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$47
No similar experiences found
Viator
Small-Group Montepulciano and Pienza Day Trip from Siena
Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy the landscapes and have lunch on a local farm! Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.
4.9(322)
8 hours
Siena, Italy
Free cancellation
English
From
$225
No similar experiences found
Headout
From Florence: Private Small-Group Tour of Siena, Cortona, Montepulciano, and Val d'Orcia with Local Tastings
Discover Siena, Cortona, Montepulciano, and the UNESCO-listed Val d’Orcia on a small-group Tuscany day trip from Florence.
0.0(0)
Siena, Italy
Free cancellation
Instant confirmation
EnglishSpanishFrench+17
From
$255
No similar experiences found
© myTour in Italy
Tiqets
Chianti & Castles: Day Trip from San Gimignano + Wine Tasting
Admire the beauty of the Italian countryside with this memorable tour. Stroll through ancient churches, medieval castles, and towns where life's rhythm remains untouched by time.
0.0(0)
6 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$99
No similar experiences found
Musement
San Gimignano, Chianti and Montalcino Tour from Siena with Wine Tasting
Visit the medieval San Gimignano, explore the Chianti region and taste the renowned Brunello of Montalcino.
4.2(6)
11 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$165
No similar experiences found
Viator
Small-Group San Gimignano and Volterra Day Trip from Siena
Embrace the medieval charms of Tuscany's towns on a full-day trip to San Gimignano and Volterra from Siena. With an attentive local guide, walk round the Fortress of Monteriggioni, explore the UNESCO World Heritage-listed town of San Gimignano, and visit an alabaster workshop in Volterra. Enjoy a delicious lunch on a small Tuscan farm and spend time at your leisure exploring these rustic hill towns that are steeped in rich Italian history. Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.
4.9(200)
8 hours
Siena, Italy
Free cancellation
Likely to sell out
English
From
$225
No similar experiences found
Headout
From Rome: Tuscany & Siena Day Trip by High-Speed Train with Lunch & Wine Tasting
Escape Rome for a day and discover the very best of Tuscany.
0.0(0)
Siena, Italy
Free cancellation
EnglishSpanishFrench+17
From
$282
No similar experiences found
© MY TOUR - MY RENT S.R.L.
Tiqets
Chianti: Guided Tour from Siena + Wine & Olive Oil Tasting
Take a half-day trip from Siena through the Chianti region. You'll pass vineyards, hills, and medieval villages. Visit historic churches and castles, then stop at a winery in the Chianti Classico area.
0.0(0)
5 hours
Siena, Italy
Free cancellation
Instant confirmation
EnglishItalianSpanish
From
$99
No similar experiences found

Musement

Guided walking tour of Siena

4.1(10)

1 hour

Siena, Italy

Free cancellation
Instant confirmation

From

$47

Viator

Small-Group Montepulciano and Pienza Day Trip from Siena

4.9(322)

8 hours

Siena, Italy

Free cancellation

From

$225

Headout

From Florence: Private Small-Group Tour of Siena, Cortona, Montepulciano, and Val d'Orcia with Local Tastings

0.0(0)

Siena, Italy

Free cancellation
Instant confirmation

From

$255

Tiqets

Chianti & Castles: Day Trip from San Gimignano + Wine Tasting

0.0(0)

6 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$99

Musement

San Gimignano, Chianti and Montalcino Tour from Siena with Wine Tasting

4.2(6)

11 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$165

Viator

Small-Group San Gimignano and Volterra Day Trip from Siena

4.9(200)

8 hours

Siena, Italy

Free cancellation
Likely to sell out

From

$225

Headout

From Rome: Tuscany & Siena Day Trip by High-Speed Train with Lunch & Wine Tasting

0.0(0)

Siena, Italy

Free cancellation

From

$282

Tiqets

Chianti: Guided Tour from Siena + Wine & Olive Oil Tasting

0.0(0)

5 hours

Siena, Italy

Free cancellation
Instant confirmation

From

$99

Private & luxury experiences in Siena

Private guides, VIP access, after-hours tours, premium small-group

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Viator
Discover the Medieval Charm of Siena on a Private Walking Tour
Decide with your guide if you want to have a 2 or 3 hours tour! Discover the treasures of one of the most beautiful cities in the world through the eyes of a local and immerse yourself in its art, culture and traditions as the horse race the Palio, which takes place twice a year. Stroll in the ancient streets and admire the Basilica of San Domenico, the St. Catherine of Siena Church, Piazza del Campo, Palazzo Pubblico, ancient palaces, the important pilgrims road, the Baptistery and the Cathedral. If you wish, visit also the inside of the Cathedral, where you will admire the artworks of important Italian artists, such as Michelangelo, Donatello and Bernini. If you are more interested in the Palio tradition, we suggest to visit a Contrada Museum. You will find out why this horse race is so important for the Sienese and admire the prizes won over the centuries. Customize your tour with your guide!
4.8(263)
2 hours - 3 hours
Siena, Italy
Free cancellation
Private tour
GermanEnglishItalian+2
From
$183
No similar experiences found
Viator
Private Tour: Secret Siena Walking Tour
Discover the older parts of Siena’s medieval centre and see hidden corners away from the crowded tourist areas, an exceptional itinerary to discover the quieter side of Siena.
5.0(116)
3 hours
Siena, Italy
Free cancellation
Private tour
GermanEnglishItalian+1
From
$331
No similar experiences found
Viator
Siena Private Walking Tour: Traditions, Streets & Cathedral
Explore Siena on a private walking tour with an expert local guide and discover the city beyond the main tourist routes. Walk through the historic center, step into the city’s unique contrada neighborhoods, and learn about their traditions, identity, and centuries-old rivalries. Enjoy a guided visit inside Siena Cathedral (Duomo) with skip-the-line entry, and experience the city’s everyday life, artisan corners, hidden streets, and local food culture along the way. - Private walking tour of Siena with an expert local guide. - Historic center and Siena’s iconic contrada neighborhoods. - Skip-the-line entry and guided visit inside Siena Cathedral (Duomo) - Local food traditions, artisan culture, and hidden streets. - Choose a 2-hour intro tour or upgrade to the 3-hour extended tour. -Available in English, German, and French language options.
4.5(81)
2 hours - 3 hours
Siena, Italy
Free cancellation
Private tour
GermanEnglishFrench
From
$182
No similar experiences found
Viator
Private Tour: Siena Walking Tour
Siena, 'the pearl of the Gothic style,' is a charming medieval town in the center of Tuscany. Come and discover the hidden treasures of this medieval town and the surroundings with a professional tour guide.
5.0(51)
2 hours
Siena, Italy
Free cancellation
Private tour
PortugueseEnglishItalian+1
From
$213
No similar experiences found
Viator
Siena Tour and exclusive window on Piazza del Campo
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!
4.8(41)
2 hours
Siena, Italy
Free cancellation
Private tour
EnglishItalian
From
$207
No similar experiences found
Viator
Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour
Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive a tour of an organic dairy farm followed by a cheese tasting. Visit the beautiful Renaissance gem that is the hilltown of Pienza and enjoy lunch at your own leisure. Explore the hill town of Montalcino, and taste the rich flavours of the famous Brunello wine directly from a producer. Visit the farm, tour the cellars and learn more about this memorable nectar.
5.0(40)
8 hours
Siena, Italy
Free cancellation
Private tour
GermanChineseEnglish+3
From
$828
No similar experiences found
Viator
Hunt for the 10 Treasures of Siena
If you are looking for a unique and fun activity to involve the whole family in the interactive discovery of the most hidden but no less fascinating places in Siena, you cannot miss our Treasure Hunt! Furthermore, instant photography will allow you to appreciate the beauties of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be customized, to be browsed whenever you want. Find out all the details, solve the puzzles and answer the quizzes to transform your visit to Siena into a unique memory to share with the whole family, young and old, and with friends. N.B. In the days of the Palio (29 June-2 July and 13-16 August) the treasure hunt route is not feasible and is replaced with that of the Top 10 dedicated to the places of the Palio, of which we will provide a dedicated guide and map.
5.0(40)
1 hour - 4 hours
Siena, Italy
Free cancellation
Private tour
EnglishItalian
From
$73
No similar experiences found
Viator
Siena Medieval Power Quest: Self-Guided Family Feud Game
Unravel the secrets of medieval Siena through a thrilling quest of power, rivalry, and hidden history. This isn’t just a walk - it’s an adventure through time. Guided by your phone, you’ll follow in the footsteps of Siena’s powerful families as you solve 9 clever puzzles tied to the city’s most iconic landmarks and lesser-known corners. You’ll explore places like Fonte Gaia, Piazza del Duomo, Palazzo Tolomei, and even the world’s second-oldest bank - all while uncovering the dramatic story of a family’s rise to power during the Middle Ages. Every solved clue reveals another piece of the city’s rich history. What makes this tour unique? It blends real-world exploration with a historical escape game, letting you experience Siena not just as a tourist, but as part of its medieval drama. Perfect for families, couples, or solo travelers who love history, mystery, and a bit of strategy. Play at your own pace, offline or online—no schedule, no pressure.
4.2(39)
1 hour - 1 hr 30 min
Siena, Italy
Free cancellation
Private tour
Special offer
GermanEnglishItalian+2
From
$9
No similar experiences found

Viator

Discover the Medieval Charm of Siena on a Private Walking Tour

4.8(263)

2 hours - 3 hours

Siena, Italy

Free cancellation
Private tour

From

$183

Viator

Private Tour: Secret Siena Walking Tour

5.0(116)

3 hours

Siena, Italy

Free cancellation
Private tour

From

$331

Viator

Siena Private Walking Tour: Traditions, Streets & Cathedral

4.5(81)

2 hours - 3 hours

Siena, Italy

Free cancellation
Private tour

From

$182

Viator

Private Tour: Siena Walking Tour

5.0(51)

2 hours

Siena, Italy

Free cancellation
Private tour

From

$213

Viator

Siena Tour and exclusive window on Piazza del Campo

4.8(41)

2 hours

Siena, Italy

Free cancellation
Private tour

From

$207

Viator

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

5.0(40)

8 hours

Siena, Italy

Free cancellation
Private tour

From

$828

Viator

Hunt for the 10 Treasures of Siena

5.0(40)

1 hour - 4 hours

Siena, Italy

Free cancellation
Private tour

From

$73

Viator

Siena Medieval Power Quest: Self-Guided Family Feud Game

4.2(39)

1 hour - 1 hr 30 min

Siena, Italy

Free cancellation
Private tour
Special offer

From

Siena tour FAQs

Common questions about booking Siena experiences through SimilarTours

When's the best time to visit Siena?

Late April through May and September through October hit the sweet spot - warm, less crowded than July-August, and the landscape is at its greenest or most golden. Summer gets very hot and packed with tour groups. Winter is quieter but many smaller restaurants and attractions have reduced hours, so check before you go.

How far ahead should I book tours?

Hot air balloon flights and multi-day wine experiences fill up weeks in advance, especially in peak season, so book those as soon as your dates are set. City tours and transfers can often be arranged with a few days' notice, but earlier is always safer.

Are guided tours worth it in Siena?

Yes, especially for wine regions outside the city - a guide transforms a winery visit from a tasting into a real understanding of the soil and history. For the city itself, a family tour or walking guide can save you getting lost in the one-way alleys, though Siena's small enough to wander on your own if you're comfortable with a map.

What's the best way to get around the region?

Most visitors hire a private driver or book a shared tour van to reach villages like Montalcino, Montepulciano, and San Gimignano - the roads wind, parking is tight, and you'll want your hands free for tasting. If you're staying a few days, a rental car works too, but book accommodation with parking.

Can I bring kids to Siena?

Absolutely. City walking tours designed for families are available, and the Piazza del Campo is basically a stage for running around. Wine tastings and multi-day food tours are typically adult-focused, but many restaurants are family-friendly. Check age policies for specific experiences before booking.

What should I expect from a Tuscan wine tour?

Most full-day tours include visits to 2-3 wineries, tastings of multiple wines (often Brunello or Chianti depending on the valley), and usually a lunch or snacks paired with local food. Private tours tend to go deeper into one region, while shared tours cover more ground. All-day experiences typically run 6-8 hours, so wear comfortable shoes and eat breakfast.

Can I book a transfer to Rome from Siena?

Yes, private transfers and driver tours that stop at places like Orvieto and Montepulciano on the way are popular options. It's a scenic 3-4 hour drive, and many travellers prefer a guided stop or two over the direct route. Check timing and what's included when you book.