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 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 Florence Accademia Gallery Tour & Timed Entry Tickets Included 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 Florence Duomo Complex Private Guided Tour 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 driver for Florence city sightseeing & Wine Tour Chianti

Hi I'm Gianluca, I was born in Florence and I have a long experience on Tours, I know my places and I love to show …More

Florence, Italy

5.0 (2)

Private driver for Florence city sightseeing & Wine Tour Chianti

Hi I'm Gianluca, I was born in Florence and I have a long experience on Tours, I know my places and I love to show...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$930

Private Pisa & Tuscany Wine Tour with Tasting & Lunch

Experience the best of Tuscany on this private shore excursion from Livorno, combining the world-famous Leaning Tower of Pisa with an authentic Tuscany wine tour. …More

Livorno, Italy

5.0 (4)

Private Pisa & Tuscany Wine Tour with Tasting & Lunch

Experience the best of Tuscany on this private shore excursion from Livorno, combining the world-famous Leaning Tower of Pisa with an authentic Tuscany wine tour....

8 hours Free Cancellation

5.0 (4)

from
$226

Wine Tour Bolgheri Half Day Shore Excursion from Livorno Port

Relax and enjoy the beauty of Tuscany on this 6-hour tour from Livorno to the countryside of Bolgheri. Your English-speaking driver/guide will take you from …More

Livorno, Italy

5.0 (4)

Wine Tour Bolgheri Half Day Shore Excursion from Livorno Port

Relax and enjoy the beauty of Tuscany on this 6-hour tour from Livorno to the countryside of Bolgheri. Your English-speaking driver/guide will take you from...

9 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$865

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences * …More

Siena, Italy

5.0 (2)

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences *...

10 hours Hotel pickup offered

5.0 (2)

from
$272

Wine Tour Bolgheri Half day Shore Excursion from Piombino Port

Relax and enjoy the beauty of Tuscany on this 6-hour tour from Piombino to the countryside of Bolgheri. Your English-speaking driver/guide will take you from …More

Livorno, Italy

5.0 (3)

Wine Tour Bolgheri Half day Shore Excursion from Piombino Port

Relax and enjoy the beauty of Tuscany on this 6-hour tour from Piombino to the countryside of Bolgheri. Your English-speaking driver/guide will take you from...

6 hours Free Cancellation

5.0 (3)

from
$865

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
$281

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

Pisa, Lucca & Cheese Farm with wine tasting Private Tour

Discover the Tuscan Countryside, two famous towns and cheeses heritage of the region. You will visit Pisa, an ancient maritime city, is an unmissable destination …More

Florence, Italy

5.0 (2)

Pisa, Lucca & Cheese Farm with wine tasting Private Tour

Discover the Tuscan Countryside, two famous towns and cheeses heritage of the region. You will visit Pisa, an ancient maritime city, is an unmissable destination...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$402

Private E-bike Tour in Chianti from Florence

Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills …More

Florence, Italy

5.0 (4)

Private E-bike Tour in Chianti from Florence

Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills...

7 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$303

Private E-bike Tour in Chianti from San Gimignano

Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills …More

San Gimignano, Italy

4.7 (3)

Private E-bike Tour in Chianti from San Gimignano

Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills...

6 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$299

Private San Gimignano Wine Tour from Livorno Port

Indulge yourself with a pleasant trip to the medieval cities of San Gimignano and Volterra. Admire the Tuscan countryside and take lovely pictures of the gently …More

Livorno, Italy

5.0 (4)

Private San Gimignano Wine Tour from Livorno Port

Indulge yourself with a pleasant trip to the medieval cities of San Gimignano and Volterra. Admire the Tuscan countryside and take lovely pictures of the gently...

9 hours

5.0 (4)

from
$982

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads, …More

Siena, Italy

5.0 (2)

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads,...

6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$340

Wine lovers experience in Montepulciano: full day

Certo, ecco la traduzione in inglese: This tour is designed for true wine lovers who wish to discover Montepulciano through its wines and wineries, enjoying …More

Montepulciano, Italy

4.4 (5)

Wine lovers experience in Montepulciano: full day

Certo, ecco la traduzione in inglese: This tour is designed for true wine lovers who wish to discover Montepulciano through its wines and wineries, enjoying...

6 hours Free Cancellation

4.4 (5)

from
$399

San Gimignano and Siena Private Wine Tasting Tour with Lunch

This tour includes a car at your disposal during the tour and a transfer to San Gimignano, where you’ll have free time to explore the …More

Lucca, Italy

5.0 (4)

San Gimignano and Siena Private Wine Tasting Tour with Lunch

This tour includes a car at your disposal during the tour and a transfer to San Gimignano, where you’ll have free time to explore the...

9 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$227

Chianti e-bike tour from Florence with wine tasting

Bike tour to discover the hills around Florence, the beautiful area of Chianti Colli Fiorentini and Chianti Classico. The tour start from San Donato, small …More

San Gimignano, Italy

5.0 (3)

Chianti e-bike tour from Florence with wine tasting

Bike tour to discover the hills around Florence, the beautiful area of Chianti Colli Fiorentini and Chianti Classico. The tour start from San Donato, small...

6 hours Free Cancellation

5.0 (3)

from
$217

Chianti Region and San Gimignano including wine tasting and light lunch

Indulge in the perfect tour for those seeking to explore the Tuscan Countryside. Your private driver, at your disposal for the day, will guide you …More

Florence, Italy

5.0 (3)

Chianti Region and San Gimignano including wine tasting and light lunch

Indulge in the perfect tour for those seeking to explore the Tuscan Countryside. Your private driver, at your disposal for the day, will guide you...

8 to 9 hours

5.0 (3)

from
$362

Private wine & Evo Oils Tasting with Vegetarian Meal

Take a break in a Tuscan atmosphere with a vegetarian lunch or dinner. The experience will start with a detailed introduction to the agricultural methods …More

San Gimignano, Italy

5.0 (2)

Private wine & Evo Oils Tasting with Vegetarian Meal

Take a break in a Tuscan atmosphere with a vegetarian lunch or dinner. The experience will start with a detailed introduction to the agricultural methods...

90 to 120 minutes Free Cancellation

5.0 (2)

from
$78

San Gimignano: Vineyard and Cellar Tour with Wine Tasting

This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in …More

San Gimignano, Italy

5.0 (2)

San Gimignano: Vineyard and Cellar Tour with Wine Tasting

This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$52

Private Wine Tour in Tuscany Florence Limo Service English driver

A 6 hours wine tour with an expert driver English speaking that will drive you to see the best that from the countryside of Tuscany …More

Florence, Italy

5.0 (4)

Private Wine Tour in Tuscany Florence Limo Service English driver

A 6 hours wine tour with an expert driver English speaking that will drive you to see the best that from the countryside of Tuscany...

6 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$953

A full day in the Bolgheri DOC area, one of the most famous wine regions in our country. Today we will visit 2 wineries and …More

Livorno, Italy

5.0 (2)

Bolgheri Wine Tour from Livorno

A full day in the Bolgheri DOC area, one of the most famous wine regions in our country. Today we will visit 2 wineries and...

7 to 8 hours Free Cancellation

5.0 (2)

from
$1,004

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?