Top Tuscany Luxury & Special Occasions

Q: Which Tuscany Luxury & Special Occasions have Instant Confirmation?

Tuscany Luxury & Special Occasions with Instant Confirmation include: Skip the line David Guided Experience Florence Accademia Gallery Tour & Timed Entry Tickets Included Half-Day Chianti Wine Tasting from Florence with Two Wineries Half-Day Excursion to Pisa and the Leaning Tower from Florence Private Golf Cart Tour: Michelangelo & Florence Hills View all Tours with Instant Confirmation →

Q: I need a ride! Which Tuscany Luxury & Special Occasions have Hotel Pickup?

No problem. These Tuscany Luxury & Special Occasions include Hotel Pickup: Cinque Terre and Pisa Tower Small-Group Day Trip from Florence Private Day Trip Siena, San Gimignano and Chianti from Florence The Accademia Gallery Private Tour to Cinque Terre from Florence Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano 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 →

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

Guided tour with wine tasting and local organic products

The guided tour of our winery and facilities is unique for its contents and the architectural richness of our environments, as well as for the …More

Florence, Italy

5.0 (12)

Guided tour with wine tasting and local organic products

The guided tour of our winery and facilities is unique for its contents and the architectural richness of our environments, as well as for the...

2 hours Free Cancellation

5.0 (12)

from
$46

Private Classic Wine Tour in Chianti from Florence

Chianti Classico is more than just wine—it’s a way of life. On this tour, you will discover the passion, history, and unique terroir that make …More

Florence, Italy

5.0 (4)

Private Classic Wine Tour in Chianti from Florence

Chianti Classico is more than just wine—it’s a way of life. On this tour, you will discover the passion, history, and unique terroir that make...

7 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$300

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

Wine Tour in the Countryside of Lucca with Lunch - with Minivan

This tour is including a car at your disposal during the tour, transfer to a beautiful winery in Montecarlo where you can taste 4 different …More

Lucca, Italy

5.0 (11)

Wine Tour in the Countryside of Lucca with Lunch - with Minivan

This tour is including a car at your disposal during the tour, transfer to a beautiful winery in Montecarlo where you can taste 4 different...

5 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$195

Tour of San Gimignano and Private Wine Experience in Chianti

Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in …More

Florence, Italy

5.0 (2)

Tour of San Gimignano and Private Wine Experience in Chianti

Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in...

5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$221

Private Wine Safari! Off-Road, Lunch in Winery in Tuscany!

Release your inner WHINO and join us for a wine safari in the heart of Tuscany! On our tour, you will indulge your senses with …More

Florence, Italy

5.0 (3)

Private Wine Safari! Off-Road, Lunch in Winery in Tuscany!

Release your inner WHINO and join us for a wine safari in the heart of Tuscany! On our tour, you will indulge your senses with...

5 hours Free Cancellation

5.0 (3)

from
$226

Sidecar tour in Florence and Chianti with wine tasting and lunch

This option is for wine lovers. With 45 minutes ride we’ll get to the Chianti area and meet one of our favourite winemaker. We’ll visit …More

Florence, Italy

5.0 (10)

Sidecar tour in Florence and Chianti with wine tasting and lunch

This option is for wine lovers. With 45 minutes ride we’ll get to the Chianti area and meet one of our favourite winemaker. We’ll visit...

5 hours Free Cancellation

5.0 (10)

from
$296

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

Private Guided Tour of Montepulciano with wine tasting

The Montepulciano tour will allow you to discover one of the most fascinating towns of the area, the so-called “Renaissance pearl” sheltered inside Medieval city …More

Montepulciano, Italy

5.0 (15)

Private Guided Tour of Montepulciano with wine tasting

The Montepulciano tour will allow you to discover one of the most fascinating towns of the area, the so-called “Renaissance pearl” sheltered inside Medieval city...

2 hours Free Cancellation

5.0 (15)

from
$30

- Very knowledgeable drivers with explanation about wine, food and general history of Tuscany. - Greve, the wine capital, is the most important of the …More

Florence, Italy

5.0 (16)

Private Chianti Wine Tour

- Very knowledgeable drivers with explanation about wine, food and general history of Tuscany. - Greve, the wine capital, is the most important of the...

8 hours Free Cancellation

5.0 (16)

from
$689

Wine Tour Experience at Agricola Tamburini

To experience the top of tuscany!!! drinking real taste wines and enjoyng the authenthic atmosphere of a family business!!! …More

Livorno, Italy

5.0 (12)

Wine Tour Experience at Agricola Tamburini

To experience the top of tuscany!!! drinking real taste wines and enjoyng the authenthic atmosphere of a family business!!!...

1 to 30 minutes Free Cancellation

5.0 (12)

from
$63

Private tour from Livorno port to Chianti Wine Region

This private tour will make you discover and enjoy the essence of this land known for its breathtaking landscapes that for centuries has been giving …More

Livorno, Italy

5.0 (5)

Private tour from Livorno port to Chianti Wine Region

This private tour will make you discover and enjoy the essence of this land known for its breathtaking landscapes that for centuries has been giving...

9 hours Free Cancellation

5.0 (5)

from
$250

Chianti Wine Tasting Tour from Florence (2 Wineries)

WINE LOVERS, ARE YOU READY? This is a must do day trip for Wine Lovers! We will pick you up directly by your accommodation in …More

Florence, Italy

5.0 (13)

Chianti Wine Tasting Tour from Florence (2 Wineries)

WINE LOVERS, ARE YOU READY? This is a must do day trip for Wine Lovers! We will pick you up directly by your accommodation in...

8 hours Hotel pickup offered Free Cancellation

5.0 (13)

from
$1,118

Private Assisi & Sagrantino Wines Experience from Florence

True travelers are always driven by a desire to discover new places. This same curiosity inspires those who visit the birthplace of the famous Saint …More

Florence, Italy

5.0 (2)

Private Assisi & Sagrantino Wines Experience from Florence

True travelers are always driven by a desire to discover new places. This same curiosity inspires those who visit the birthplace of the famous Saint...

13 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$748

Florence and Wine Tasting Private Tour from Livorno

ARE YOU READY FOR A GREAT DAY with LIMOSERVICEINITALY? FLORENCE AND WINE TASTING IN TUSCANY Enjoy a day exploring the highlights of Florence and a …More

Livorno, Italy

5.0 (13)

Florence and Wine Tasting Private Tour from Livorno

ARE YOU READY FOR A GREAT DAY with LIMOSERVICEINITALY? FLORENCE AND WINE TASTING IN TUSCANY Enjoy a day exploring the highlights of Florence and a...

9 hours Hotel pickup offered Free Cancellation

5.0 (13)

from
$1,004

This full day tour is perfect for first time visitors or anyone interested in combining sightseeing and a complete wine & food experience in Tuscany …More

Florence, Italy

5.0 (10)

Tuscany off the beaten paths

This full day tour is perfect for first time visitors or anyone interested in combining sightseeing and a complete wine & food experience in Tuscany...

8 hours Free Cancellation

5.0 (10)

from
$217

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

Private tour: The Gothic Line in Borgo a Mozzano (Lucca)

During this private 3-hour guided tour of the Gothic Line you will visit the Museum of the Liberation, enjoy a walking tour exploring two of …More

Lucca, Italy

5.0 (12)

Private tour: The Gothic Line in Borgo a Mozzano (Lucca)

During this private 3-hour guided tour of the Gothic Line you will visit the Museum of the Liberation, enjoy a walking tour exploring two of...

3 hours Free Cancellation

5.0 (12)

from
$195

Siena Tour and exclusive window on Piazza del Campo

A two hours enchanting walk, discovering Siena most beloved places. Start in front of the Basilica San Domenico, where the relics of St. Catherine are …More

Siena, Italy

5.0 (13)

Siena Tour and exclusive window on Piazza del Campo

A two hours enchanting walk, discovering Siena most beloved places. Start in front of the Basilica San Domenico, where the relics of St. Catherine are...

2 hours Free Cancellation

5.0 (13)

from
$40

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Tuscany Luxury & Special Occasions?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Tuscany Luxury & Special Occasions are:

What are the best kid-friendly options for Tuscany Luxury & Special Occasions Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Tuscany Luxury & Special Occasions are:

View all kid-friendly Tours →

Which Tuscany Luxury & Special Occasions have Instant Confirmation?

Which Tuscany Luxury & Special Occasions have Free Cancellation?

Tuscany Luxury & Special Occasions 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 Luxury & Special Occasions have Hotel Pickup?

Got any more Tuscany trip ideas?

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