Top Tuscany Luxury & Special Occasions

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 →

Horseback Riding in the Tuscan Vineyards

Open the doors of the Sienese countryside on horseback and immerse yourself in the breathtaking landscapes of the Tuscan countryside. Cross vineyards, rivers, olive groves …More

Siena, Italy

4.8 (10)

Horseback Riding in the Tuscan Vineyards

Open the doors of the Sienese countryside on horseback and immerse yourself in the breathtaking landscapes of the Tuscan countryside. Cross vineyards, rivers, olive groves...

1 hour Free Cancellation

4.8 (10)

from
$74

Montepulciano Wine Tasting in the Tuscan Countryside

An intimate and relaxing experience that begins with a tour of the winery and the cellar, followed by a tasting of 3 wines from our …More

Montepulciano, Italy

4.9 (10)

Montepulciano Wine Tasting in the Tuscan Countryside

An intimate and relaxing experience that begins with a tour of the winery and the cellar, followed by a tasting of 3 wines from our...

45 minutes Free Cancellation

4.9 (10)

from
$28

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 Free Cancellation

5.0 (10)

from
$189

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

Looking to see as much of Florence as possible in a short amount of time? Need a break from walking but still want to explore …More

Florence, Italy

4.8 (10)

Best of Florence Electric Bike Tour

Looking to see as much of Florence as possible in a short amount of time? Need a break from walking but still want to explore...

3 hours Free Cancellation

4.8 (10)

from
$68

Chianti Half Day Wine Tasting Tour from Siena

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in …More

Siena, Italy

4.8 (10)

Chianti Half Day Wine Tasting Tour from Siena

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in...

5 hours Free Cancellation

4.8 (10)

from
$56

Viola Park Guided Tour Discover ACF Fiorentina's Home Base

Visit the state-of-the-art Viola Park, ACF Fiorentina's new training facility in Bagno a Ripoli, Florence. This unique guided tour allows fans to explore one of …More

Florence, Italy

4.9 (10)

Viola Park Guided Tour Discover ACF Fiorentina's Home Base

Visit the state-of-the-art Viola Park, ACF Fiorentina's new training facility in Bagno a Ripoli, Florence. This unique guided tour allows fans to explore one of...

2 hours Free Cancellation

4.9 (10)

from
$103

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

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

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
$295

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

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
$954

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

Discover All the Hidden Gems of Tuscany with our Ultimate Seven-day Tour... If you would like to experience the real Tuscany avoiding tourist areas, this …More

Florence, Italy

5.0 (10)

Authentic 7 Day Tuscany Tour

Discover All the Hidden Gems of Tuscany with our Ultimate Seven-day Tour... If you would like to experience the real Tuscany avoiding tourist areas, this...

8 days Hotel pickup offered

5.0 (10)

from
$3,705

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

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?

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?

Tuscany Luxury & Special Occasions with Instant Confirmation include:

View all Tours with 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?

No problem. These Tuscany Luxury & Special Occasions 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?