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: 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 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

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

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 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

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

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

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 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

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
$313

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

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

Private Montalcino and Pienza Tour from Siena

Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as …More

4.0 (3)

Private Montalcino and Pienza Tour from Siena

Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as...

6 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$324

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will …More

4.6 (10)

Private wine tour of Chianti

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will...

6 to 8 hours Hotel pickup offered Free Cancellation

4.6 (10)

from
$325

Siena Private Walking Tour With A Professional Guide

The historic city of Siena is an enriched destination, with medieval history, beautiful architecture, and colorful culture. This UNESCO listed city has numerous medieval sculptures, …More

4.7 (3)

Siena Private Walking Tour With A Professional Guide

The historic city of Siena is an enriched destination, with medieval history, beautiful architecture, and colorful culture. This UNESCO listed city has numerous medieval sculptures,...

2 hours Free Cancellation

4.7 (3)

from
$335

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads, …More

5.0 (2)

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads,...

6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$340

That's a short but exhaustive tour that touches the most important places of the beautiful city center of Siena. …More

5.0 (4)

Let's discover Siena!

That's a short but exhaustive tour that touches the most important places of the beautiful city center of Siena....

90 to 120 minutes Free Cancellation

5.0 (4)

from
$344

Capture your memories of Siena on camera with this private photo shoot in the heart of the city. The experience is led by a professional …More

5.0 (4)

Private Photo Shoot in Siena

Capture your memories of Siena on camera with this private photo shoot in the heart of the city. The experience is led by a professional...

1 hour 30 minutes Free Cancellation

5.0 (4)

from
$358

2 hour Siena Private Guided Walking Tour

Get your Walking Tour in Siena and discover its culture, incredible sites, stories & legends with entertaining and passionate professional guides. See the artistic, religious, and cultural treasures …More

5.0 (2)

2 hour Siena Private Guided Walking Tour

2 hours Free Cancellation

5.0 (2)

from
$377

Embark on this Full-Day Private Montalcino and Montepulciano Wine Tour and indulge your senses in the heart of Italy's renowned wine country! Your day begins …More

Full-Day Private Montalcino & Montepulciano Wine Tour from Siena

Embark on this Full-Day Private Montalcino and Montepulciano Wine Tour and indulge your senses in the heart of Italy's renowned wine country! Your day begins...

7 hours Hotel pickup offered Free Cancellation

from
$419

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?