Top Tuscany Private Sightseeing Tours

Q: Got any more Tuscany trip ideas?

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

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

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

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

Siena, Italy

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

Private wine & Evo Oils Tasting with Vegetarian Meal

Take a break in a Tuscan atmosphere with a vegetarian lunch or dinner. The experience will start with a detailed introduction to the agricultural methods …More

San Gimignano, Italy

5.0 (2)

Private wine & Evo Oils Tasting with Vegetarian Meal

Take a break in a Tuscan atmosphere with a vegetarian lunch or dinner. The experience will start with a detailed introduction to the agricultural methods...

90 to 120 minutes Free Cancellation

5.0 (2)

from
$78

San Gimignano: Vineyard and Cellar Tour with Wine Tasting

This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in …More

San Gimignano, Italy

5.0 (2)

San Gimignano: Vineyard and Cellar Tour with Wine Tasting

This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$52

A full day in the Bolgheri DOC area, one of the most famous wine regions in our country. Today we will visit 2 wineries and …More

Livorno, Italy

5.0 (2)

Bolgheri Wine Tour from Livorno

A full day in the Bolgheri DOC area, one of the most famous wine regions in our country. Today we will visit 2 wineries and...

7 to 8 hours Free Cancellation

5.0 (2)

from
$1,004

A beautiful tour to discover Chianti Classico and its secrets with the only electric mini moke in Tuscany, you will have the opportunity to admire …More

Florence, Italy

5.0 (2)

"Dolce Vita" in Chiantishire

A beautiful tour to discover Chianti Classico and its secrets with the only electric mini moke in Tuscany, you will have the opportunity to admire...

5 to 6 hours

5.0 (2)

from
$746

Today we will take you to the famous Wine Region of Bolgheri where some of the best wines in the World are produced. We will …More

Lucca, Italy

5.0 (2)

Bolgheri Wine Tour from Lucca

Today we will take you to the famous Wine Region of Bolgheri where some of the best wines in the World are produced. We will...

8 hours Hotel pickup offered

5.0 (2)

from
$1,004

Montalcino and Brunello Wine Private Tour

- Very knowledgeable drivers with explanation about wine, food and general history of the area. - Visit the picturesque town of Montalcino in the Val …More

Florence, Italy

5.0 (2)

Montalcino and Brunello Wine Private Tour

- Very knowledgeable drivers with explanation about wine, food and general history of the area. - Visit the picturesque town of Montalcino in the Val...

9 hours Free Cancellation

5.0 (2)

from
$1,022

Private Fully Customized Tour of Magical Landmarks of Florence

This tour will be fully customized, so I would like to suggest you some of my favorite must-see or hidden gems in Florence to choose …More

Florence, Italy

5.0 (2)

Private Fully Customized Tour of Magical Landmarks of Florence

This tour will be fully customized, so I would like to suggest you some of my favorite must-see or hidden gems in Florence to choose...

6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$965

Florence Private Day Trip to Pisa and Lucca

A customized day trip of Pisa and Lucca for the discerning traveler seeking an authentic Italian experience on a small group tour with only the …More

Florence, Italy

5.0 (2)

Florence Private Day Trip to Pisa and Lucca

A customized day trip of Pisa and Lucca for the discerning traveler seeking an authentic Italian experience on a small group tour with only the...

9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,044

Private Day Trip to Montalcino and Montepulciano from Florence

Embark on a 9-hour private tour from Florence to the Tuscan Brunello vineyards, the perfect excursion for the discerning traveler and wine enthusiast. Travel from the …More

Florence, Italy

5.0 (2)

Private Day Trip to Montalcino and Montepulciano from Florence

Embark on a 9-hour private tour from Florence to the Tuscan Brunello vineyards, the perfect excursion for the discerning traveler and wine enthusiast. Travel from the...

9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,362

Private 4-Hour Tour of Florence with private driver and guide with Hotel pick-up

Florence is one of the most beautiful cities in the world and it has so many wonderful sights that you can enjoy. With an official …More

Florence, Italy

5.0 (2)

Private 4-Hour Tour of Florence with private driver and guide with Hotel pick-up

Florence is one of the most beautiful cities in the world and it has so many wonderful sights that you can enjoy. With an official...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$221

Private driver from Florence: Siena, San Gimignano, Pisa 12 hours

A long intense day where we will see the main city of Tuscany: Pisa, San Gimignano & Siena. Learn about it's history, culture and heritage. …More

Florence, Italy

5.0 (2)

Private driver from Florence: Siena, San Gimignano, Pisa 12 hours

A long intense day where we will see the main city of Tuscany: Pisa, San Gimignano & Siena. Learn about it's history, culture and heritage....

12 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,630

Private Florence Highlights Tour from Duomo to Old Bridge Signoria & Santa Croce

This private walking tour, led by an expert guide will introduce you to the winding streets and stunning piazzas of Florence. This tailored tour will …More

Florence, Italy

5.0 (2)

Private Florence Highlights Tour from Duomo to Old Bridge Signoria & Santa Croce

This private walking tour, led by an expert guide will introduce you to the winding streets and stunning piazzas of Florence. This tailored tour will...

2 hours Free Cancellation

5.0 (2)

from
$91

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

Siena, Italy

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

Choose a private tour to arrange it as you wish; visit with a professional tour guide your favorite handcraft shop. …More

Florence, Italy

5.0 (2)

Private Tour Around Local Handcrafts

Choose a private tour to arrange it as you wish; visit with a professional tour guide your favorite handcraft shop....

3 hours Free Cancellation

5.0 (2)

from
$321

Florence is a city so rich in art and history, it could overwhelm you and your kids. This is why I have tailored a fun …More

Florence, Italy

5.0 (2)

Florence for kids: private tour

Florence is a city so rich in art and history, it could overwhelm you and your kids. This is why I have tailored a fun...

2 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$230

Private Tour of the Dark Heart of Florence at Sunset

Florence, the cradle of Renaissance, home of the greatest artists of history has a less bright side which will conquer you. Let yourself be captivated …More

Florence, Italy

5.0 (2)

Private Tour of the Dark Heart of Florence at Sunset

Florence, the cradle of Renaissance, home of the greatest artists of history has a less bright side which will conquer you. Let yourself be captivated...

2 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$250

Private Guided Tour: Pisa and Lucca from Florence

• Experience for your party (private guided tour) Travel through Tuscany’s rolling hills and vineyards lined with Cypress Trees, from Florence to Pisa and Lucca …More

Florence, Italy

5.0 (2)

Private Guided Tour: Pisa and Lucca from Florence

• Experience for your party (private guided tour) Travel through Tuscany’s rolling hills and vineyards lined with Cypress Trees, from Florence to Pisa and Lucca...

9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$999

Private Walking Tour Best of Florence with original David by Michelangelo Discover the best of Florence and see the original David by Michelangelo …More

Florence, Italy

5.0 (2)

Private Walking Tour Best of Florence with original David by Michelangelo

Private Walking Tour Best of Florence with original David by Michelangelo Discover the best of Florence and see the original David by Michelangelo...

3 hours Hotel pickup offered

5.0 (2)

from
$344

Pisa, Lucca & Winery Private Tour from Livorno port

TDC - Drivers for Shore Excursions & Bike Tours provides professional drivers for private shore excursions from Livorno port. Our drivers will be pleased to …More

Livorno, Italy

5.0 (2)

Pisa, Lucca & Winery Private Tour from Livorno port

TDC - Drivers for Shore Excursions & Bike Tours provides professional drivers for private shore excursions from Livorno port. Our drivers will be pleased to...

8 hours Free Cancellation

5.0 (2)

from
$746

Frequently Asked Questions

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

What are the best options for Tuscany Private Sightseeing Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Tuscany Private Sightseeing Tours are:

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

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Tuscany Private Sightseeing Tours are:

View all kid-friendly Tours →

Which Tuscany Private Sightseeing Tours have Instant Confirmation?

Tuscany Private Sightseeing Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Tuscany Private Sightseeing Tours have Free Cancellation?

Tuscany 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 Tuscany Private Sightseeing Tours have Hotel Pickup?

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

View all Tours with Hotel Pickup →

Got any more Tuscany trip ideas?

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