Top Tuscany Private Sightseeing Tours

Q: Which Tuscany Private Sightseeing Tours have Instant Confirmation?

Tuscany Private Sightseeing Tours with Instant Confirmation include: Chianti Heli Wine Tour Fly Brunello - Heli Wine Tour Four Days Private Tuscany City Tour from Florence Luxury Balloon Tour in Tuscany Tuscany Multi Day Bike Tour History Wine and Local Flavors View all Tours with Instant Confirmation →

Q: I need a ride! Which Tuscany Private Sightseeing Tours have Hotel Pickup?

No problem. These Tuscany Private Sightseeing Tours include Hotel Pickup: Chianti Heli Wine Tour Fly Brunello - Heli Wine Tour Four Days Private Tuscany City Tour from Florence Luxury Balloon Tour in Tuscany Three Days Tuscany Winery Tour from Florence View all Tours with Hotel Pickup →

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 Chianti Classico Wine Tasting Tour in Two Family Wineries

Live an authentic experience in the heart of Chianti Classico with a visit to two family-run wineries, where you will be welcomed directly by the …More

Florence, Italy

5.0 (27)

Private Chianti Classico Wine Tasting Tour in Two Family Wineries

Live an authentic experience in the heart of Chianti Classico with a visit to two family-run wineries, where you will be welcomed directly by the...

5 hours Hotel pickup offered Free Cancellation

5.0 (27)

from
$184

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

Siena, Italy

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

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

Siena, Italy

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
$182

Cycling Pisa highlights & hidden treasures - half day tour

This is the perfect tour for first time visitors who have a short time (half day) and wish to explore Pisa around and beyond the …More

Pisa, Italy

5.0 (44)

Cycling Pisa highlights & hidden treasures - half day tour

This is the perfect tour for first time visitors who have a short time (half day) and wish to explore Pisa around and beyond the...

3 hours Free Cancellation

5.0 (44)

from
$183

Accessible Cinque Terre and Pisa Private Excursion from Livorno

Designed for guests with limited mobility or who use a mobility aid, our accessible Cinque Terre & Pisa shore excursion from Livorno is the perfect …More

Livorno, Italy

5.0 (3)

Accessible Cinque Terre and Pisa Private Excursion from Livorno

Designed for guests with limited mobility or who use a mobility aid, our accessible Cinque Terre & Pisa shore excursion from Livorno is the perfect...

8 to 9 hours Free Cancellation

5.0 (3)

from
$183

Accessible and Hassle-Free Cinque Terre Private Tour from Livorno

Designed for guests with limited mobility or who use a mobility aid, our accessible Cinque Terre shore excursion from Livorno is the perfect way to …More

Livorno, Italy

4.0 (1)

Accessible and Hassle-Free Cinque Terre Private Tour from Livorno

Designed for guests with limited mobility or who use a mobility aid, our accessible Cinque Terre shore excursion from Livorno is the perfect way to...

8 to 9 hours Free Cancellation

4.0 (1)

from
$183

Urban Bikery wants to pay tribute to the prestigious territory in which it has its headquarters by organizing a 100% eco-sustainable wine tour in an …More

Montepulciano, Italy

4.9 (159)

Wine Tour Ebike Experience

Urban Bikery wants to pay tribute to the prestigious territory in which it has its headquarters by organizing a 100% eco-sustainable wine tour in an...

5 hours Free Cancellation

4.9 (159)

from
$183

Best of Florence Tour with Uffizi and David

A licensed expert guide will lead you on a fascinating private guided walking tour through the streets and piazzas of Florence. Discover the best that …More

Florence, Italy

5.0 (5)

Best of Florence Tour with Uffizi and David

A licensed expert guide will lead you on a fascinating private guided walking tour through the streets and piazzas of Florence. Discover the best that...

4 hours

5.0 (5)

from
$183

Private Excursion to Siena, San Gimignano and Chianti Landscapes

Embark on an unforgettable private tour starting from your hotel. Visit the historic city of Siena, where you’ll enjoy an exclusive guided tour of its …More

Florence, Italy

4.8 (22)

Private Excursion to Siena, San Gimignano and Chianti Landscapes

Embark on an unforgettable private tour starting from your hotel. Visit the historic city of Siena, where you’ll enjoy an exclusive guided tour of its...

8 hours Hotel pickup offered Free Cancellation

4.8 (22)

from
$182

From Livorno Port: Private Cinque Terre & Porto Venere Tour

Discover the magic of Porto Venere and the Cinque Terre with a private tour and a private driver-guide, perfect for cruise passengers or anyone staying …More

Livorno, Italy

5.0 (1)

From Livorno Port: Private Cinque Terre & Porto Venere Tour

Discover the magic of Porto Venere and the Cinque Terre with a private tour and a private driver-guide, perfect for cruise passengers or anyone staying...

10 hours Free Cancellation

5.0 (1)

from
$182

From Livorno Port: Private Pisa & Florence Day Tour

Two of the most beautiful art cities in the world, in one private day from Livorno Port. • Pick-up right under your cruise ship at …More

Livorno, Italy

5.0 (1)

From Livorno Port: Private Pisa & Florence Day Tour

Two of the most beautiful art cities in the world, in one private day from Livorno Port. • Pick-up right under your cruise ship at...

9 hours

5.0 (1)

from
$182

Private wine tour on the magical hills of Lucca with sommelier

I'm Simone Vergamini, "Best Sommelier of Tuscany 2023", 3rd place at the Best Sommelier of Italy 2018, 2021, 2022, and it will be a pleasure …More

Lucca, Italy

5.0 (80)

Private wine tour on the magical hills of Lucca with sommelier

I'm Simone Vergamini, "Best Sommelier of Tuscany 2023", 3rd place at the Best Sommelier of Italy 2018, 2021, 2022, and it will be a pleasure...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (80)

from
$182

The Best of Tuscany: Private Full Day Tour From Florence

This immersive experience is tailored for travelers who yearn to explore the breathtaking beauty and rich culture of Tuscany in depth, all in the span …More

Florence, Italy

5.0 (59)

The Best of Tuscany: Private Full Day Tour From Florence

This immersive experience is tailored for travelers who yearn to explore the breathtaking beauty and rich culture of Tuscany in depth, all in the span...

9 hours Hotel pickup offered Free Cancellation

5.0 (59)

from
$182

Experience the essence of Tuscany on this full-day private tour from Florence, visiting Pisa, Siena, and San Gimignano in total comfort. Start with convenient pickup …More

Florence, Italy

5.0 (4)

Day Trip Pisa, Siena, San Gimignano.

Experience the essence of Tuscany on this full-day private tour from Florence, visiting Pisa, Siena, and San Gimignano in total comfort. Start with convenient pickup...

11 hours Free Cancellation

5.0 (4)

from
$182

From Florence: Private Volterra, San Gimignano & Wine Lunch

A private day from Florence to two of the most beautiful hill towns of Tuscany, with a wine lunch at a family-run farm. • Pick-up …More

Florence, Italy

5.0 (2)

From Florence: Private Volterra, San Gimignano & Wine Lunch

A private day from Florence to two of the most beautiful hill towns of Tuscany, with a wine lunch at a family-run farm. • Pick-up...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$180

PRIVATE Florence Food Tour & Wine with Local Expert Marina

Discover Florence through its food on a private tasting tour with Martina, a knowledgeable local food expert passionate about Tuscan cuisine. Visit local eateries and …More

Florence, Italy

5.0 (9)

PRIVATE Florence Food Tour & Wine with Local Expert Marina

Discover Florence through its food on a private tasting tour with Martina, a knowledgeable local food expert passionate about Tuscan cuisine. Visit local eateries and...

2 to 3 hours Free Cancellation

5.0 (9)

from
$179

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

Siena, Italy

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

KIDS TOUR FREE! Family-Friendly Pisa & Florence from Livorno

This kid-friendly tour to Florence & Pisa is fun for the whole family! Can be geared towards children of any age, or teens. KIDS 12 …More

Livorno, Italy

4.6 (5)

KIDS TOUR FREE! Family-Friendly Pisa & Florence from Livorno

This kid-friendly tour to Florence & Pisa is fun for the whole family! Can be geared towards children of any age, or teens. KIDS 12...

8 to 9 hours

4.6 (5)

from
$178

Private Uffizi Gallery Guided Tour in Florence

A private tour to explore the glory of the masterpieces from the past at the Uffizi Gallery, where the world’s finest collection of Renaissance paintings …More

Florence, Italy

4.8 (5)

Private Uffizi Gallery Guided Tour in Florence

A private tour to explore the glory of the masterpieces from the past at the Uffizi Gallery, where the world’s finest collection of Renaissance paintings...

1 hour 30 minutes Free Cancellation

4.8 (5)

from
$177

Private day trip to Siena, San Gimignano, Chianti and Pisa, from Florence

Get the maximum flexibility, comfort and privacy with a private customizable service, just for your party. Your professional and expert English speaking driver, will explain …More

Florence, Italy

4.9 (135)

Private day trip to Siena, San Gimignano, Chianti and Pisa, from Florence

Get the maximum flexibility, comfort and privacy with a private customizable service, just for your party. Your professional and expert English speaking driver, will explain...

10 hours Hotel pickup offered Free Cancellation

4.9 (135)

from
$177

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?

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?

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?

Got any more Tuscany trip ideas?

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