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 →

Montepulciano, Pienza, and the Essence of Val d'Orcia

Embark on an exclusive Val d’Orcia tour, starting from Florence or any Tuscan location, for an unforgettable journey through rolling hills, medieval towns, and world-renowned …More

Florence, Italy

5.0 (11)

Montepulciano, Pienza, and the Essence of Val d'Orcia

Embark on an exclusive Val d’Orcia tour, starting from Florence or any Tuscan location, for an unforgettable journey through rolling hills, medieval towns, and world-renowned...

10 to 11 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$297

Discover Florence’s city center’s treasures and striking views from an unusual viewpoint: by bike! Cycle off leisurely, escorted by your dedicated private guide, through ancient …More

Florence, Italy

5.0 (11)

Florence Private Vintage Bike Tour

Discover Florence’s city center’s treasures and striking views from an unusual viewpoint: by bike! Cycle off leisurely, escorted by your dedicated private guide, through ancient...

2 hours Free Cancellation

5.0 (11)

from
$86

From Livorno Port: Private Volterra, San Gimignano & Wine Lunch

Spend a day through the Chianti sweet hills. A wonderful Experience between art, wine and local food to discover vineyards, towers and typical farms. • …More

Livorno, Italy

5.0 (10)

From Livorno Port: Private Volterra, San Gimignano & Wine Lunch

Spend a day through the Chianti sweet hills. A wonderful Experience between art, wine and local food to discover vineyards, towers and typical farms. •...

8 hours Hotel pickup offered Free Cancellation

5.0 (10)

from
$238

Florence Dome Climb & Private Guided Sightseeing Walking Tour with Hotel Pickup

This private walking tour begins when you meet with your guide at your centrally-located hotel to discover the wonderful Renaissance city of Florence. The tour …More

Florence, Italy

5.0 (10)

Florence Dome Climb & Private Guided Sightseeing Walking Tour with Hotel Pickup

This private walking tour begins when you meet with your guide at your centrally-located hotel to discover the wonderful Renaissance city of Florence. The tour...

3 hours Free Cancellation

5.0 (10)

from
$126

Private Tour: Medieval Val d'Orcia by Minivan from Florence

Leaving from Florence, this 9-hours tour by air-conditioned minivan will let you dive into the breathtaking and delicate Val d'Orcia. In this valley you will …More

Florence, Italy

4.9 (10)

Private Tour: Medieval Val d'Orcia by Minivan from Florence

Leaving from Florence, this 9-hours tour by air-conditioned minivan will let you dive into the breathtaking and delicate Val d'Orcia. In this valley you will...

9 hours Hotel pickup offered Free Cancellation

4.9 (10)

from
$165

The guided visit of the Cathedral and its floor is a journey full of excitement. Come with Tuscany Art Trek and enjoy nearly a thousand …More

Siena, Italy

4.8 (10)

Siena Cathedral: shrine of treasures.

The guided visit of the Cathedral and its floor is a journey full of excitement. Come with Tuscany Art Trek and enjoy nearly a thousand...

1 hour 30 minutes Free Cancellation

4.8 (10)

from
$149

Two magic hours to discover the city with Your children! Children and adults will learn the city's history having fun and being enriched by anecdotes …More

Siena, Italy

4.8 (10)

Siena Family Tour

Two magic hours to discover the city with Your children! Children and adults will learn the city's history having fun and being enriched by anecdotes...

2 hours Free Cancellation

4.8 (10)

from
$33

Pisa and San Gimignano Tour from Florence

Enjoy a day visiting Pisa, famous for the Leaning Tower and San Gimignano know as the "Manhattan of the Middle Ages". Incredible landscapes, history and …More

Florence, Italy

4.9 (10)

Pisa and San Gimignano Tour from Florence

Enjoy a day visiting Pisa, famous for the Leaning Tower and San Gimignano know as the "Manhattan of the Middle Ages". Incredible landscapes, history and...

8 to 9 hours Hotel pickup offered Free Cancellation

4.9 (10)

from
$1,022

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan …More

Siena, Italy

5.0 (10)

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan...

8 hours Hotel pickup offered

5.0 (10)

from
$227

Pisa and Florence Private Tour with Wine Tasting

Discover the Essence of Tuscany: Pisa, Florence & Chianti Wine Experience Immerse yourself in the timeless beauty of Pisa and Florence—two of Tuscany’s most iconic …More

Livorno, Italy

4.9 (10)

Pisa and Florence Private Tour with Wine Tasting

Discover the Essence of Tuscany: Pisa, Florence & Chianti Wine Experience Immerse yourself in the timeless beauty of Pisa and Florence—two of Tuscany’s most iconic...

9 hours

4.9 (10)

from
$1,255

Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes "Under The Tuscan Sun"). Located between Florence and Rome, Cortona …More

Arezzo, Italy

5.0 (10)

Cortona private walking Tour

Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes "Under The Tuscan Sun"). Located between Florence and Rome, Cortona...

2 hours 30 minutes Free Cancellation

5.0 (10)

from
$132

Cinque Terre Private with the leaning tower Pisa from Florence

Cinque Terre is the star of the Italian Riviera, the five fishing villages are listed as UNESCO World Heritage Site. Riomaggiore, Manarola and Vernazza were …More

Florence, Italy

5.0 (10)

Cinque Terre Private with the leaning tower Pisa from Florence

Cinque Terre is the star of the Italian Riviera, the five fishing villages are listed as UNESCO World Heritage Site. Riomaggiore, Manarola and Vernazza were...

9 hours Free Cancellation

5.0 (10)

from
$965

Florence, Lucca and Pisa Private Tour from Livorno

9-hour tour Round trip transportation from/to the port/ship Comfortable air conditioning minivan Professional tour guide-driver English speaking driver Enjoy the Tuscan landscapes while driving Florence …More

Florence, Italy

5.0 (10)

Florence, Lucca and Pisa Private Tour from Livorno

9 hours

5.0 (10)

from
$1,255

Shore excursion from Livorno to Pisa and Lucca

This tour can be family oriented but also adventurous. We take you to the back roads and places to get a glimpse of real Italy …More

Livorno, Italy

5.0 (10)

Shore excursion from Livorno to Pisa and Lucca

This tour can be family oriented but also adventurous. We take you to the back roads and places to get a glimpse of real Italy...

8 hours Free Cancellation

5.0 (10)

from
$1,251

Pisa & Florence highlights shore excursion from Livorno port

Top of the range Mercedes private minivan transfer, WIFI on board, air conditioning, drivers available for the duration of the tour, English speaking driver. …More

Livorno, Italy

5.0 (10)

Pisa & Florence highlights shore excursion from Livorno port

Top of the range Mercedes private minivan transfer, WIFI on board, air conditioning, drivers available for the duration of the tour, English speaking driver....

8 to 9 hours Free Cancellation

5.0 (10)

from
$983

From Florence Assisi and Carlo Acutis and Orvieto Day Trip

Escape Florence for a full day private journey into the heart of Umbria, a land of vineyards, olive groves, and charming hilltop villages. Explore Assisi, …More

Florence, Italy

4.9 (10)

From Florence Assisi and Carlo Acutis and Orvieto Day Trip

Escape Florence for a full day private journey into the heart of Umbria, a land of vineyards, olive groves, and charming hilltop villages. Explore Assisi,...

10 hours Free Cancellation

4.9 (10)

from
$213

Private Day Trip San Gimignano and Volterra from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Dedicate one day to the magnificent cities of San Gimignano and Volterra, and explore the history of the …More

Florence, Italy

5.0 (9)

Private Day Trip San Gimignano and Volterra from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Dedicate one day to the magnificent cities of San Gimignano and Volterra, and explore the history of the...

8 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$130

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

Luxury Shopping Experience: Private Chauffeur to The Mall & Prada

An unforgettable journey into the world of fashion: The Mall & Prada Space. Spend an half day in two of the best the shopping centers …More

Florence, Italy

5.0 (9)

Luxury Shopping Experience: Private Chauffeur to The Mall & Prada

An unforgettable journey into the world of fashion: The Mall & Prada Space. Spend an half day in two of the best the shopping centers...

6 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$148

Florence Top-Sites Guided Tour with Michelangelo David

Meet your local guide at your lodging and begin this strolling voyage through Florence. This visit will carry you into the center of a standout …More

Florence, Italy

4.9 (9)

Florence Top-Sites Guided Tour with Michelangelo David

Meet your local guide at your lodging and begin this strolling voyage through Florence. This visit will carry you into the center of a standout...

3 hours

4.9 (9)

from
$124

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?

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?