Top Siena Private Sightseeing Tours

Q: What are the best options for Siena Private Sightseeing Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Siena Private Sightseeing Tours are: Private Vintage Fiat 500 tour in Chianti Private Tour: Guided Hike in Tuscany with Transport from Siena Siena Private Walking Tour with a Local Siena private guided tour for families Private Guided Tour of Siena with a Licensed Local Tour Guide

Q: What are the best kid-friendly options for Siena Private Sightseeing Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Siena Private Sightseeing Tours are: Three Hours Siena Private Walking Tour with Personal Photographer Private Off Road Wine Tour in Chianti from Siena Private wine tour of Chianti Private Montalcino and Pienza Tour from Siena Private Vintage Fiat 500 tour in Chianti From Siena View all kid-friendly Tours →

Q: Which Siena Private Sightseeing Tours have Instant Confirmation?

Siena Private Sightseeing Tours with Instant Confirmation include: Private Hot Air Balloon to Pienza, Montalcino and Val D'orcia Private Tour: Tuscany Hot Air Balloon Flight from Siena Chianti Wines and San Gimignano Tour from Florence (1 Winery) The Maremma Three Hours Siena Private Walking Tour with Personal Photographer View all Tours with Instant Confirmation →

Q: I need a ride! Which Siena Private Sightseeing Tours have Hotel Pickup?

No problem. These Siena Private Sightseeing Tours include Hotel Pickup: Brunello/Montalcino-Tour in Ferrari Siena to Rome: Orvieto and Montepulciano Transfer Tour Private Siena to Florence Chianti and San Gimignano Transfer Tour The Maremma Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour View all Tours with Hotel Pickup →

Q: Got any more Siena trip ideas?

We sure do. Check out our curated lists of hand-picked Siena Tours. Top 10 Siena 2026 Senior-friendly tours Siena The best tours and activities for culture lovers in Siena Top Day Trips from Siena Things to do in Siena this summer View all Siena Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Siena?

Based on our sales data over the past year, the most popular styles of tours and activities in Siena are: Siena Cultural & Theme Tours Siena Historical & Heritage Tours Siena Luxury & Special Occasions Siena Luxury Tours Siena Walking & Biking Tours View all tour styles in Siena →

Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from SIENA

Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint …More

5.0 (2)

Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from SIENA

Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint...

9 hours Hotel pickup offered

5.0 (2)

from
$227

Private Tour: Guided Hike in Tuscany with Transport from Siena

Explore Tuscany's picturesque rolling hills on a private, full-day hiking and sight-seeing tour with transport from Siena. Enjoy a scenic, full-day adventure with your expert …More

5.0 (7)

Private Tour: Guided Hike in Tuscany with Transport from Siena

Explore Tuscany's picturesque rolling hills on a private, full-day hiking and sight-seeing tour with transport from Siena. Enjoy a scenic, full-day adventure with your expert...

7 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$217

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 …More

5.0 (43)

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...

2 hours Free Cancellation

5.0 (43)

from
$204

Guided tour of Siena for groups including children, that also adults can enjoy. Your professional guide will guide you through the city of Siena and …More

5.0 (1)

Kid tour in Siena

Guided tour of Siena for groups including children, that also adults can enjoy. Your professional guide will guide you through the city of Siena and...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$204

Uncover the soul of Tuscany on this 8-hour private tour through three of its most iconic towns: Siena, San Gimignano, and Monteriggioni. Travel in style …More

Siena, San Gimignano and Monteriggioni Wine Tasting and Tour

Uncover the soul of Tuscany on this 8-hour private tour through three of its most iconic towns: Siena, San Gimignano, and Monteriggioni. Travel in style...

8 hours Free Cancellation

from
$196

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small …More

5.0 (35)

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small...

8 hours Hotel pickup offered

5.0 (35)

from
$194

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

* Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Siena * Private and exclusive service * 8 hours in …More

5.0 (7)

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

* Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Siena * Private and exclusive service * 8 hours in...

8 hours Hotel pickup offered

5.0 (7)

from
$193

Cycle at your own pace with a local English-speaking guide who can tell you about the area. Admire the famous Chianti Classico wine area close …More

5.0 (2)

Chianti Classico Bike Tour from Siena

Cycle at your own pace with a local English-speaking guide who can tell you about the area. Admire the famous Chianti Classico wine area close...

4 hours

5.0 (2)

from
$184

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 …More

4.7 (19)

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...

7 hours 15 minutes Free Cancellation

4.7 (19)

from
$179

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and …More

5.0 (2)

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and...

5 hours 20 minutes Free Cancellation

5.0 (2)

from
$176

Discover the secrets of the most authentic Tuscan Maremma, guided by expert Maremmagica personnel, immersed in the uncontaminated nature of the Diaccia Botrona Regional Nature …More

5.0 (1)

Walking tour in Diaccia Botrona

Discover the secrets of the most authentic Tuscan Maremma, guided by expert Maremmagica personnel, immersed in the uncontaminated nature of the Diaccia Botrona Regional Nature...

2 to 3 hours Free Cancellation

5.0 (1)

from
$163

The guided visit of the Cathedral and its floor is a journey full of excitement. Come with Tuscany Art Trek and enjoy nearly a thousand …More

4.8 (10)

Siena Cathedral: shrine of treasures.

The guided visit of the Cathedral and its floor is a journey full of excitement. Come with Tuscany Art Trek and enjoy nearly a thousand...

1 hour 30 minutes Free Cancellation

4.8 (10)

from
$149

Siena to Florence Private Transfer: Monteriggioni & San Gimignano

Turn your transfer from Siena to Florence into a visit to two of the most famous medieval towns of Tuscany, crossing the Chianti area, in …More

5.0 (3)

Siena to Florence Private Transfer: Monteriggioni & San Gimignano

Turn your transfer from Siena to Florence into a visit to two of the most famous medieval towns of Tuscany, crossing the Chianti area, in...

5 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$136

The Cathedral of Siena is an overwhelming monument that houses works of art from the Middle Ages to the contemporary period. Inside the church you …More

5.0 (2)

Siena Cathedral: Private Tour

The Cathedral of Siena is an overwhelming monument that houses works of art from the Middle Ages to the contemporary period. Inside the church you...

1 hour Free Cancellation

5.0 (2)

from
$136

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

If you choose to see the Medieval Tuscany with us, after meeting you in front of your residence, we will take you with a short …More

5.0 (14)

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

If you choose to see the Medieval Tuscany with us, after meeting you in front of your residence, we will take you with a short...

8 to 9 hours Free Cancellation

5.0 (14)

from
$122

On this private walking tour you will explore a city declared a UNESCO World Heritage Site. You will visit its most important places, such as …More

5.0 (2)

Siena Private Walking Tour

On this private walking tour you will explore a city declared a UNESCO World Heritage Site. You will visit its most important places, such as...

2 to 3 hours Free Cancellation

5.0 (2)

from
$115

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 …More

4.6 (78)

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...

2 to 3 hours Free Cancellation

4.6 (78)

from
$112

The Most Delicious Private Food Tour of Siena: 10 Tastings

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked …More

5.0 (11)

The Most Delicious Private Food Tour of Siena: 10 Tastings

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked...

3 hours Free Cancellation

5.0 (11)

from
$110

Siena Street Food Tour With 4 or more Tastings

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, …More

4.8 (12)

Siena Street Food Tour With 4 or more Tastings

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,...

3 hours Free Cancellation

4.8 (12)

from
$98

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 …More

5.0 (23)

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...

1 to 4 hours Free Cancellation

5.0 (23)

from
$71

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Siena Private Sightseeing Tours?

What are the best kid-friendly options for Siena Private Sightseeing Tours Tours?

Which Siena Private Sightseeing Tours have Instant Confirmation?

Which Siena Private Sightseeing Tours have Free Cancellation?

Siena Private Sightseeing Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Siena Private Sightseeing Tours have Hotel Pickup?

Got any more Siena trip ideas?

What are the most popular styles of Tours and Activities in Siena?