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: 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 →

Private Vintage Fiat 500 tour in Chianti From Siena

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s …More

5.0 (1)

Private Vintage Fiat 500 tour in Chianti From Siena

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$320

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 …More

4.9 (108)

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...

3 hours Free Cancellation

4.9 (108)

from
$318

Discover the highlights of Chianti Classico while riding through Tuscany’s backroads in a Land Rover Defender. There is a special kind of magic in driving …More

5.0 (20)

Private Off Road Wine Tour in Chianti

Discover the highlights of Chianti Classico while riding through Tuscany’s backroads in a Land Rover Defender. There is a special kind of magic in driving...

6 hours Free Cancellation

5.0 (20)

from
$310

Private Tour: Montalcino Wine Tasting Experience

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this …More

5.0 (71)

Private Tour: Montalcino Wine Tasting Experience

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this...

8 hours Hotel pickup offered Free Cancellation

5.0 (71)

from
$308

Private Vintage Fiat 500 tour in Chianti

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s …More

5.0 (2)

Private Vintage Fiat 500 tour in Chianti

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s...

6 hours Free Cancellation

5.0 (2)

from
$294

Private Grape stomping in Chianti from Siena

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of …More

5.0 (1)

Private Grape stomping in Chianti from Siena

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$278

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors …More

5.0 (4)

Private Ebike Tour in Chianti

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors...

6 hours Free Cancellation

5.0 (4)

from
$274

From Siena: Private Volterra, San Gimignano & Wine Lunch

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at …More

5.0 (4)

From Siena: Private Volterra, San Gimignano & Wine Lunch

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at...

8 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$272

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences * …More

5.0 (2)

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences *...

10 hours Hotel pickup offered

5.0 (2)

from
$272

Fascinating walk to discover Siena, the most famous monuments and the least known and most precious places. We will walk through alleys and medieval streets, …More

5.0 (7)

Siena private guided tour for families

Fascinating walk to discover Siena, the most famous monuments and the least known and most precious places. We will walk through alleys and medieval streets,...

2 hours Free Cancellation

5.0 (7)

from
$264

From Siena: Private Brunello & Nobile Wine Tour with Lunch

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello …More

5.0 (3)

From Siena: Private Brunello & Nobile Wine Tour with Lunch

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello...

9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$261

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their …More

5.0 (5)

Private Truffle Hunting in Chianti

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their...

5 hours Free Cancellation

5.0 (5)

from
$257

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

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

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

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

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

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

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

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?