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 →

Wine Tour of two Chianti wine estates on the hills of Florence

This tour grants the access to authentic historical wineries producing high quality wines of two different Chianti subzones. In this private tour the guest is …More

Florence, Italy

5.0 (2)

Wine Tour of two Chianti wine estates on the hills of Florence

This tour grants the access to authentic historical wineries producing high quality wines of two different Chianti subzones. In this private tour the guest is...

5 hours Free Cancellation

5.0 (2)

from
$333

Livorno Port ShorExcursion: Siena San Gimignano Lunch&WineTasting

Enjoy this unforgettable Shore Excursion and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • …More

Livorno, Italy

4.0 (1)

Livorno Port ShorExcursion: Siena San Gimignano Lunch&WineTasting

Enjoy this unforgettable Shore Excursion and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: •...

9 hours

4.0 (1)

from
$333

Private tour San Gimignano, Chianti and Wine Tasting with lunch

Enjoy this private tour immersed in Tuscan countryside nature, culture and local wine and food. You will adore amazing views on the way to San …More

Florence, Italy

5.0 (3)

Private tour San Gimignano, Chianti and Wine Tasting with lunch

Enjoy this private tour immersed in Tuscan countryside nature, culture and local wine and food. You will adore amazing views on the way to San...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$332

Sitting on top of a hill at the junction of the 4 valleys that compose its province, Arezzo was a great Etruscan and Roman city. …More

Arezzo, Italy

5.0 (8)

Arezzo Private Tour with Official Guide

Sitting on top of a hill at the junction of the 4 valleys that compose its province, Arezzo was a great Etruscan and Roman city....

2 hours Free Cancellation

5.0 (8)

from
$331

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This …More

Florence, Italy

5.0 (18)

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This...

10 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$330

Private Chianti Tuscany Wine Tasting Tour from Florence

Get a driver guide and let him drive you while you enjoy the flavors of Chianti wine. For our well-rounded experience, we will take you …More

Florence, Italy

5.0 (2)

Private Chianti Tuscany Wine Tasting Tour from Florence

Get a driver guide and let him drive you while you enjoy the flavors of Chianti wine. For our well-rounded experience, we will take you...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$330

Exclusive Private Tuscany Wine Tour & Food Pairing Session

ALL INCLUDED PRIVATE WINE TOUR to 3 selected wineries of Tuscany mainly around the prestigious Chianti Classico area. Wineries are selected by a LEVEL 3 …More

Florence, Italy

4.9 (72)

Exclusive Private Tuscany Wine Tour & Food Pairing Session

ALL INCLUDED PRIVATE WINE TOUR to 3 selected wineries of Tuscany mainly around the prestigious Chianti Classico area. Wineries are selected by a LEVEL 3...

8 hours Hotel pickup offered Free Cancellation

4.9 (72)

from
$329

Private Renaissance Discovery Tour of Florence

Go deep into Florence artistic heritage and let your professional private guide unveil every corner of the cradle of Renaissance. An enlightening guided promenade at …More

Florence, Italy

4.8 (8)

Private Renaissance Discovery Tour of Florence

Go deep into Florence artistic heritage and let your professional private guide unveil every corner of the cradle of Renaissance. An enlightening guided promenade at...

3 hours Hotel pickup offered Free Cancellation

4.8 (8)

from
$329

Lucca Royal Experience – Grand Tour Deluxe by Carriage (2 Hours)

Discover Lucca in all its beauty with the 2-hour deluxe carriage tour. This experience allows you to cross the historic center and walk the entire …More

Lucca, Italy

5.0 (42)

Lucca Royal Experience – Grand Tour Deluxe by Carriage (2 Hours)

Discover Lucca in all its beauty with the 2-hour deluxe carriage tour. This experience allows you to cross the historic center and walk the entire...

2 hours Free Cancellation

5.0 (42)

from
$328

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

Siena, Italy

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
$326

Private Vintage Fiat 500 Tour in Chianti From Florence

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

Florence, Italy

5.0 (2)

Private Vintage Fiat 500 Tour in Chianti From Florence

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 (2)

from
$323

Livorno Shore Excursion: Exclusive Wine Experience

You can decide whether you'd like to spend more time at the winery and just visit San Gimignano, then stop in Pisa. Alternatively, you can …More

Livorno, Italy

3.0 (1)

Livorno Shore Excursion: Exclusive Wine Experience

You can decide whether you'd like to spend more time at the winery and just visit San Gimignano, then stop in Pisa. Alternatively, you can...

5 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$323

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

Siena, Italy

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
$321

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

Siena, Italy

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

Full-Day Livorno Shore Excursion to Pisa and Florence

With this private shore exscursion from the port of Livorno an english speaking driver will pick you up in minivan and take you to Pisa …More

Livorno, Italy

5.0 (1)

Full-Day Livorno Shore Excursion to Pisa and Florence

With this private shore exscursion from the port of Livorno an english speaking driver will pick you up in minivan and take you to Pisa...

8 hours Free Cancellation

5.0 (1)

from
$320

Private tour Wine and cheese a perfect combinations val 'Orcia

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a …More

Arezzo, Italy

4.6 (7)

Private tour Wine and cheese a perfect combinations val 'Orcia

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a...

8 to 9 hours Hotel pickup offered Free Cancellation

4.6 (7)

from
$320

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
$318

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

Siena, Italy

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

From Florence:Tuscany Tuk Tuk with Lunch, Wine & San Gimignano

Experience the beauty of Tuscany on a private tuk-tuk tour through the Chianti countryside! Depart from Florence by shared bus/van, then enjoy an exclusive ride …More

Florence, Italy

5.0 (16)

From Florence:Tuscany Tuk Tuk with Lunch, Wine & San Gimignano

Experience the beauty of Tuscany on a private tuk-tuk tour through the Chianti countryside! Depart from Florence by shared bus/van, then enjoy an exclusive ride...

7 hours Free Cancellation

5.0 (16)

from
$318

Florence Original Experience with a Native Guide

Experience the authentic Florence through the eyes of a born and raised 14th generation native guide, immersing your self in the local community with its …More

Florence, Italy

5.0 (37)

Florence Original Experience with a Native Guide

Experience the authentic Florence through the eyes of a born and raised 14th generation native guide, immersing your self in the local community with its...

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (37)

from
$318

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?