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 →

Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence

Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your …More

Florence, Italy

5.0 (34)

Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence

Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your...

8 hours Hotel pickup offered Free Cancellation

5.0 (34)

from
$453

Chianti Wine Tour - Private Wine experience in Tuscany Countryside

Dive into an unparalleled wine journey with our exclusive Chianti Wine Tour, starting directly from your accommodation. Onboard our luxury vehicles, driven by an experienced …More

Florence, Italy

5.0 (34)

Chianti Wine Tour - Private Wine experience in Tuscany Countryside

Dive into an unparalleled wine journey with our exclusive Chianti Wine Tour, starting directly from your accommodation. Onboard our luxury vehicles, driven by an experienced...

8 hours Hotel pickup offered Free Cancellation

5.0 (34)

from
$341

We are Italian local guides, born in Florence and you will have a unique Tuscany experience, this is a perfect day to relax after enjoying …More

Florence, Italy

4.9 (34)

Private Tour of San Gimignano & Siena

We are Italian local guides, born in Florence and you will have a unique Tuscany experience, this is a perfect day to relax after enjoying...

9 hours Hotel pickup offered Free Cancellation

4.9 (34)

from
$1,270

Private Walking Tour of Florence Highlights

Discover the city's iconic places and most fascinating monuments in a 90-minute express walking tour of Florence. Learn the secrets of the Cradle of the …More

Florence, Italy

5.0 (33)

Private Walking Tour of Florence Highlights

Discover the city's iconic places and most fascinating monuments in a 90-minute express walking tour of Florence. Learn the secrets of the Cradle of the...

1 hour 30 minutes Free Cancellation

5.0 (33)

from
$45

Chianti Wine Tour from Florence to San Gimignano with 2 Wineries

Explore the beautiful Tuscan countryside with a private driver and customize your itinerary to visit two wineries in Chianti and San Gimignano, with a 15-minute …More

Florence, Italy

5.0 (33)

Chianti Wine Tour from Florence to San Gimignano with 2 Wineries

Explore the beautiful Tuscan countryside with a private driver and customize your itinerary to visit two wineries in Chianti and San Gimignano, with a 15-minute...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (33)

from
$134

Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

Experience an unforgettable full-day chauffeur-driven adventure deep in the heart of Chianti — far from the hustle and bustle of Florence. Sit back and relax …More

Florence, Italy

4.9 (33)

Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

Experience an unforgettable full-day chauffeur-driven adventure deep in the heart of Chianti — far from the hustle and bustle of Florence. Sit back and relax...

8 hours Hotel pickup offered Free Cancellation

4.9 (33)

from
$120

The History of Florence: Famous Medici Family Private Tour

It’s the history that made the city today. During this private tour, it’s time to discover Florence through the Famous Historical Medici Family. Embark on …More

Florence, Italy

5.0 (32)

The History of Florence: Famous Medici Family Private Tour

It’s the history that made the city today. During this private tour, it’s time to discover Florence through the Famous Historical Medici Family. Embark on...

3 hours Free Cancellation

5.0 (32)

from
$47

Cinqueterre and Pisa Shore Excursion from Livorno

Enjoy the Cinque Terre region with the best views from the water, and a stop in Pisa to see the famous sites. You will be …More

Livorno, Italy

4.8 (32)

Cinqueterre and Pisa Shore Excursion from Livorno

Enjoy the Cinque Terre region with the best views from the water, and a stop in Pisa to see the famous sites. You will be...

9 hours Free Cancellation

4.8 (32)

from
$1,114

A Day of Classic Motors - Ferrari, Maserati & Lamborghini museums - private tour

Immerse yourself in these Automotive icons for the day, with a guide that has experienced ownership of both brands, ridden at Mugello many times with …More

Florence, Italy

5.0 (32)

A Day of Classic Motors - Ferrari, Maserati & Lamborghini museums - private tour

Immerse yourself in these Automotive icons for the day, with a guide that has experienced ownership of both brands, ridden at Mugello many times with...

8 hours Hotel pickup offered Free Cancellation

5.0 (32)

from
$373

Private Chianti Safari: Off Road Tuscany Wine Tour with Lunch from Florence

For connoisseurs and amateurs alike, there’s no better way to explore the famous Chianti vineyards and sample the world-class tipples for which the area is …More

Florence, Italy

5.0 (31)

Private Chianti Safari: Off Road Tuscany Wine Tour with Lunch from Florence

For connoisseurs and amateurs alike, there’s no better way to explore the famous Chianti vineyards and sample the world-class tipples for which the area is...

8 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$559

Private Day Tour of Pisa, San Gimignano and Siena from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Dedicate one day to the enchanting exploration of the three best-preserved medieval cities in the world (UNESCO World …More

Florence, Italy

5.0 (31)

Private Day Tour of Pisa, San Gimignano and Siena from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Dedicate one day to the enchanting exploration of the three best-preserved medieval cities in the world (UNESCO World...

9 to 10 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$163

Private Day Tour: Pisa and Lucca from Florence

Embark on this private day tour of both Pisa and Lucca over a total of 8 hours. Pisa, known for its architectural wonders, is home …More

Florence, Italy

5.0 (31)

Private Day Tour: Pisa and Lucca from Florence

Embark on this private day tour of both Pisa and Lucca over a total of 8 hours. Pisa, known for its architectural wonders, is home...

8 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$685

A Journey Across Tuscany’s History, Olive Oil Heritage and Beauty

Experience of some groups thrugh myself: What a beautiful day just south of Florence visiting the American World War II Memorial and Cemetery for those …More

Florence, Italy

5.0 (31)

A Journey Across Tuscany’s History, Olive Oil Heritage and Beauty

Experience of some groups thrugh myself: What a beautiful day just south of Florence visiting the American World War II Memorial and Cemetery for those...

8 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$172

Florence : Carriage Tour in the Old Town – Romantic Tour

Discover Florence from a unique perspective with an elegant horse-drawn carriage tour in the heart of the historic center. Along the way you will pass …More

Florence, Italy

5.0 (30)

Florence : Carriage Tour in the Old Town – Romantic Tour

Discover Florence from a unique perspective with an elegant horse-drawn carriage tour in the heart of the historic center. Along the way you will pass...

1 hour Free Cancellation

5.0 (30)

from
$55

Cinque Terre Shore Excursions from Livorno Port

Private shore excursion with english speaking driver and Mercedes minivan to Le Cinque Terre from Livorno port. very flexible to suits client's needs and desires …More

Livorno, Italy

4.8 (30)

Cinque Terre Shore Excursions from Livorno Port

Private shore excursion with english speaking driver and Mercedes minivan to Le Cinque Terre from Livorno port. very flexible to suits client's needs and desires...

8 to 10 hours Free Cancellation

4.8 (30)

from
$1,205

Shore Excursion from Livorno: Cinque Terre and Pisa independent private tour

This is truly a wonderful experience, one that you will treasure for life. Discover the five picturesque villages scattered along a beautiful stretch of the …More

Livorno, Italy

4.8 (29)

Shore Excursion from Livorno: Cinque Terre and Pisa independent private tour

This is truly a wonderful experience, one that you will treasure for life. Discover the five picturesque villages scattered along a beautiful stretch of the...

7 to 9 hours Free Cancellation

4.8 (29)

from
$141

Private Chianti Classico Experience from Florence

Do you want to learn more about one of the most prestigious wines in Italy and worldwide? Embark with us on this journey in the …More

Florence, Italy

5.0 (29)

Private Chianti Classico Experience from Florence

Do you want to learn more about one of the most prestigious wines in Italy and worldwide? Embark with us on this journey in the...

10 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$532

Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

Private tour to San Gimignano and Chianti with an English speaking driver in a deluxe minivan. Your driver will delight you with live commentary on …More

Florence, Italy

5.0 (29)

Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

Private tour to San Gimignano and Chianti with an English speaking driver in a deluxe minivan. Your driver will delight you with live commentary on...

8 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$139

Private Pisa and Lucca Wine Tour from Florence

Leave Florence and discover the Tuscan cities of Lucca and Pisa on a day trip. You’ll see the UNESCO-listed Leaning Tower of Pisa (entry own …More

Florence, Italy

4.8 (29)

Private Pisa and Lucca Wine Tour from Florence

Leave Florence and discover the Tuscan cities of Lucca and Pisa on a day trip. You’ll see the UNESCO-listed Leaning Tower of Pisa (entry own...

8 hours Free Cancellation

4.8 (29)

from
$201

Private Full Day Walking Tour of Florence Highlights with Uffizi and Accademia

Full day tour in Florence with timed entry tickets entrance to Uffizi and Accademia. Admire the most important sites of Florence in one day. The …More

Florence, Italy

4.9 (29)

Private Full Day Walking Tour of Florence Highlights with Uffizi and Accademia

Full day tour in Florence with timed entry tickets entrance to Uffizi and Accademia. Admire the most important sites of Florence in one day. The...

6 hours Hotel pickup offered Free Cancellation

4.9 (29)

from
$282

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?