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 →

Siena & San Gimignano: Private Tour from Florence

Perfect escape from Florence for a day and journey through the rolling hills of Tuscany to discover the fascinating medieval towns of Siena and San …More

Florence, Italy

5.0 (1)

Siena & San Gimignano: Private Tour from Florence

Perfect escape from Florence for a day and journey through the rolling hills of Tuscany to discover the fascinating medieval towns of Siena and San...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$284

Shore excursion Florence and Pisa from Livorno Port

Pick-up from your ship at Livorno Arrive in Pisa leave for Florence stop at Piazzale Michelangelo and Duomo Piazza Santa Croce stop at Piazza Duomo …More

Florence, Italy

5.0 (1)

Shore excursion Florence and Pisa from Livorno Port

Pick-up from your ship at Livorno Arrive in Pisa leave for Florence stop at Piazzale Michelangelo and Duomo Piazza Santa Croce stop at Piazza Duomo...

8 hours Free Cancellation

5.0 (1)

from
$284

Iconic Chianti Town & Two Wineries Visit Full Day Private Tour

Escape the bustling city of Florence and immerse yourself in the rolling hills, ancient vineyards, and timeless charm of the Chianti Classico wine region. On …More

Florence, Italy

5.0 (1)

Iconic Chianti Town & Two Wineries Visit Full Day Private Tour

Escape the bustling city of Florence and immerse yourself in the rolling hills, ancient vineyards, and timeless charm of the Chianti Classico wine region. On...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$284

Uffizi, Tuscan Flavors & Artisan Workshops in Florence

Discover Florence through its masterpieces, flavors, and timeless craftsmanship. Start with priority entry to the Uffizi Gallery, where your guide unveils the genius of Botticelli …More

Florence, Italy

5.0 (3)

Uffizi, Tuscan Flavors & Artisan Workshops in Florence

Discover Florence through its masterpieces, flavors, and timeless craftsmanship. Start with priority entry to the Uffizi Gallery, where your guide unveils the genius of Botticelli...

6 hours 30 minutes Hotel pickup offered

5.0 (3)

from
$282

Private Vespa Tour in Chianti from Florence

The Vespa Experience offers a unique and stylish way to explore Tuscany. Forget the chaos of daily life and enjoy the region’s stunning landscapes from …More

Florence, Italy

5.0 (9)

Private Vespa Tour in Chianti from Florence

The Vespa Experience offers a unique and stylish way to explore Tuscany. Forget the chaos of daily life and enjoy the region’s stunning landscapes from...

6 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$280

Private Day in Florence: An Immersive Experience

During the Florence in a day tour, we will take you to all the highlights of this beautiful city. Florence is well known as the …More

Florence, Italy

5.0 (5)

Private Day in Florence: An Immersive Experience

During the Florence in a day tour, we will take you to all the highlights of this beautiful city. Florence is well known as the...

7 hours Free Cancellation

5.0 (5)

from
$280

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
$280

Chianti from Florence:PRIVATE Wine, Olive Oil Tasting in the Tuscan countryside

“If you truly want to experience the Chianti region, this is the tour you’ve been looking for!” The Chianti region is celebrated worldwide for its …More

Florence, Italy

5.0 (4)

Chianti from Florence:PRIVATE Wine, Olive Oil Tasting in the Tuscan countryside

“If you truly want to experience the Chianti region, this is the tour you’ve been looking for!” The Chianti region is celebrated worldwide for its...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$279

Private Grape stomping in Chianti from Florence

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of …More

Florence, Italy

5.0 (12)

Private Grape stomping in Chianti from Florence

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$278

Ferrari Parmesan Cheese Balsamic Vinegar wine & food PRIVATE TOUR from FLORENCE

Private, Exclusive, Customizable, door-to-door tour of Modena area: * Parmesan cheese tasting * Ferrari museum * Balsamic vinegar tasting * Lambrusco tasting * Luxury Mercedes …More

Florence, Italy

5.0 (3)

Ferrari Parmesan Cheese Balsamic Vinegar wine & food PRIVATE TOUR from FLORENCE

Private, Exclusive, Customizable, door-to-door tour of Modena area: * Parmesan cheese tasting * Ferrari museum * Balsamic vinegar tasting * Lambrusco tasting * Luxury Mercedes...

10 hours Hotel pickup offered

5.0 (3)

from
$276

Orvieto, Civita di Bagnoregio, Pitigliano PRIVATE TOUR from FLORENCE

- Take this tour and discover the best Umbrian towns. Orvieto, with its Duomo and astounding array of Medieval and Renaissance religious art, is a …More

Florence, Italy

5.0 (3)

Orvieto, Civita di Bagnoregio, Pitigliano PRIVATE TOUR from FLORENCE

- Take this tour and discover the best Umbrian towns. Orvieto, with its Duomo and astounding array of Medieval and Renaissance religious art, is a...

10 hours Hotel pickup offered

5.0 (3)

from
$276

Private Grape stomping in Chianti from Siena

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of …More

Siena, Italy

5.0 (1)

Private Grape stomping in Chianti from Siena

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$275

Carrara marble quarries Cinque Terre PRIVATE TOUR from FLORENCE

- Follow in the Master's footsteps as you trace Michelangelo's tracks to the marble quarries of Carrara. Carrara is where he went (250 miles was …More

Florence, Italy

5.0 (1)

Carrara marble quarries Cinque Terre PRIVATE TOUR from FLORENCE

- Follow in the Master's footsteps as you trace Michelangelo's tracks to the marble quarries of Carrara. Carrara is where he went (250 miles was...

9 hours Hotel pickup offered

5.0 (1)

from
$274

Private Cinque Terre Tour from Livorno to Monterosso

Ideal for Cruise passengers. What makes our Cinque Terre exceptional is that is a tour thought to combine private transportation with local public transportation (ferry …More

Livorno, Italy

5.0 (3)

Private Cinque Terre Tour from Livorno to Monterosso

Ideal for Cruise passengers. What makes our Cinque Terre exceptional is that is a tour thought to combine private transportation with local public transportation (ferry...

9 hours Free Cancellation

5.0 (3)

from
$274

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors …More

Siena, Italy

5.0 (4)

Private Ebike Tour in Chianti

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors...

6 hours Free Cancellation

5.0 (4)

from
$273

Florence: Private Tour. Accademia Gallery David's Statue & Uffizi

Join a private guided tour of the most spectacular attractions in Florence: Uffizi and the famous David's statue by Michelangelo in Academia Gallery, Piazza Duomo, …More

Florence, Italy

5.0 (1)

Florence: Private Tour. Accademia Gallery David's Statue & Uffizi

Join a private guided tour of the most spectacular attractions in Florence: Uffizi and the famous David's statue by Michelangelo in Academia Gallery, Piazza Duomo,...

3 hours Hotel pickup offered

5.0 (1)

from
$273

From Pisa: Private Chianti & San Gimignano with Wine Lunch

Spend a day in the iconic landscape of the Chianti hills with a private tour from the Pisa countryside. Drive along avenues of cypress trees, …More

Pisa, Italy

5.0 (4)

From Pisa: Private Chianti & San Gimignano with Wine Lunch

Spend a day in the iconic landscape of the Chianti hills with a private tour from the Pisa countryside. Drive along avenues of cypress trees,...

8 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$273

Original Private Tuscany tour by Vintage Beetle car & Wine

Explore Tuscany in style with a classic vintage Beetle car tour from 1977. Enjoy breathtaking views, visit two renowned wineries, and taste exceptional wines including …More

4.9 (9)

Original Private Tuscany tour by Vintage Beetle car & Wine

Explore Tuscany in style with a classic vintage Beetle car tour from 1977. Enjoy breathtaking views, visit two renowned wineries, and taste exceptional wines including...

5 hours

4.9 (9)

from
$273

Private Wine Tour to Bolgheri with Expert Sommelier - 2 Wineries

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

Lucca, Italy

5.0 (2)

Private Wine Tour to Bolgheri with Expert Sommelier - 2 Wineries

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

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$272

Private Carrara Marble Quarries Jeep Tour & Wine Tasting

A private day in the Apuan Alps, led by Andrea, an authorized environmental guide who is also your private driver. • Pick-up at your hotel …More

Lucca, Italy

5.0 (1)

Private Carrara Marble Quarries Jeep Tour & Wine Tasting

A private day in the Apuan Alps, led by Andrea, an authorized environmental guide who is also your private driver. • Pick-up at your hotel...

9 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$272

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?