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: Hunt for the 10 Treasures of Siena Siena Cathedral: shrine of treasures. Siena to Florence Private Transfer: Monteriggioni & San Gimignano Siena Highlights Private Walking Tour With A Guide (Private Tour) Chianti Wines and San Gimignano Tour from Florence (1 Winery)

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: Private Guided Tour of Siena with a Licensed Local Tour Guide Private Tour of Siena Cathedral Siena Family Tour Discover the Medieval Charm of Siena on a Private Walking Tour Siena Private Walking Tour with a Local View all kid-friendly Tours →

Q: Which Siena Private Sightseeing Tours have Instant Confirmation?

Siena Private Sightseeing Tours with Instant Confirmation include: Siena Medieval Power Quest: Self-Guided Family Feud Game Siena Highlights Private Walking Tour With A Guide (Private Tour) Private Tour of Siena Cathedral Siena Family Tour Discover the Medieval Charm of Siena on a Private Walking Tour View all Tours with Instant Confirmation →

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 →

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

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

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

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

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

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

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

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

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

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

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan …More

5.0 (10)

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan...

8 hours Hotel pickup offered

5.0 (10)

from
$227

Brunello di Montalcino wine experience with a sommelier

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully …More

5.0 (3)

Brunello di Montalcino wine experience with a sommelier

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully...

5 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$228

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

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 …More

5.0 (19)

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...

5 to 6 hours Free Cancellation

5.0 (19)

from
$240

Any season has its own truffles, the black you can find almost all year round and the celebrated white ones, which season starts in October. …More

5.0 (3)

Private Truffle Hunt in Tuscany

Any season has its own truffles, the black you can find almost all year round and the celebrated white ones, which season starts in October....

4 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$241

While we take care of every detail, leave the chaos behind and enjoy the best of Tuscany’s landscapes from your stylish Vespa — perfect not …More

5.0 (7)

Private Vespa Tour in Chianti

While we take care of every detail, leave the chaos behind and enjoy the best of Tuscany’s landscapes from your stylish Vespa — perfect not...

5 hours Free Cancellation

5.0 (7)

from
$251

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally …More

4.9 (11)

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally...

4 hours Free Cancellation

4.9 (11)

from
$251

Let's discover Siena with a fascinating historical tour. Not only the most famous buildings like the church of San Domenico, the Salimbeni palace, the Chigi …More

5.0 (1)

Siena Private walking tour

Let's discover Siena with a fascinating historical tour. Not only the most famous buildings like the church of San Domenico, the Salimbeni palace, the Chigi...

2 hours Free Cancellation

5.0 (1)

from
$253

Discover with me the unknown and most fascinating Siena with this unique and unusual tour. SECRET SIENA WALKING TOUR, is my favorite to discover history, …More

4.8 (9)

Secret Siena Walking Tour

Discover with me the unknown and most fascinating Siena with this unique and unusual tour. SECRET SIENA WALKING TOUR, is my favorite to discover history,...

2 hours Free Cancellation

4.8 (9)

from
$258

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?

No problem. These Siena Private Sightseeing Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Siena trip ideas?

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