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 →

Siena Underground Wine tasting in a Medieval Cave

For real wine lovers, This is a wine tasting experience hosted by a Sommelier. This tour offers you an exclusive wine tasting in a Medieval …More

Siena, Italy

5.0 (59)

Siena Underground Wine tasting in a Medieval Cave

For real wine lovers, This is a wine tasting experience hosted by a Sommelier. This tour offers you an exclusive wine tasting in a Medieval...

1 hour Free Cancellation

5.0 (59)

from
$85

Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings

Leave the crowds of Florence behind and journey into the heart of Tuscany with a full-day tour of the stunning Val d’Orcia, a UNESCO World …More

Florence, Italy

4.8 (51)

Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings

Leave the crowds of Florence behind and journey into the heart of Tuscany with a full-day tour of the stunning Val d’Orcia, a UNESCO World...

11 hours 30 minutes Free Cancellation

4.8 (51)

from
$84

Greve in Chianti Wine Tasting and Winery Tour

Visit a small family winery, where products are organic, the company's coverage is 1 hectare of olive grove and 3 of Sangiovese, Syrah and Merlot …More

Chianti, Italy

4.8 (90)

Greve in Chianti Wine Tasting and Winery Tour

Visit a small family winery, where products are organic, the company's coverage is 1 hectare of olive grove and 3 of Sangiovese, Syrah and Merlot...

1 hour 30 minutes Free Cancellation

4.8 (90)

from
$57

Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

Private tour to San Gimignano and Chianti with an English speaking driver in a deluxe minivan. Your driver will delight you with live commentary on …More

Florence, Italy

5.0 (29)

Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

Private tour to San Gimignano and Chianti with an English speaking driver in a deluxe minivan. Your driver will delight you with live commentary on...

8 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$139

Private Guided Visit Florence's Santa Croce Basilica and Ancient Leather School

Visit the Santa Croce Basilica in Florence, a stunning Gothic architectural masterpiece known for its colorful marble façade. Once a sanctuary for Franciscan friars, the …More

Florence, Italy

4.9 (18)

Private Guided Visit Florence's Santa Croce Basilica and Ancient Leather School

Visit the Santa Croce Basilica in Florence, a stunning Gothic architectural masterpiece known for its colorful marble façade. Once a sanctuary for Franciscan friars, the...

1 hour 30 minutes Free Cancellation

4.9 (18)

from
$36

Pisa, Siena, San Gimignano Small Group with Lunch & Wine Tasting

Discover the highlights of Tuscany on a small group tour from Florence, visiting Siena, San Gimignano, and Pisa. Travel in a cozy atmosphere with a …More

Florence, Italy

4.8 (47)

Pisa, Siena, San Gimignano Small Group with Lunch & Wine Tasting

Discover the highlights of Tuscany on a small group tour from Florence, visiting Siena, San Gimignano, and Pisa. Travel in a cozy atmosphere with a...

11 hours 30 minutes Free Cancellation

4.8 (47)

from
$181

E-bike Tuscany and Chianti Self-Guided Tour with Vineyard Visit

Discover Tuscany and Florence by muscular bike or E-bike, along the amazing hills surrounding Florence and the Chianti Classico wine region. Thanks to our 30+ …More

Florence, Italy

5.0 (15)

E-bike Tuscany and Chianti Self-Guided Tour with Vineyard Visit

Discover Tuscany and Florence by muscular bike or E-bike, along the amazing hills surrounding Florence and the Chianti Classico wine region. Thanks to our 30+...

6 to 7 hours Free Cancellation

5.0 (15)

from
$29

Private Tour of Palazzo Pitti with Boboli Garden

Vieni a visitare l’ultima residenza dei Medici a Firenze con una guida locale privata. Il museo si svolge attraverso la vita quotidiana della famiglia dei …More

Florence, Italy

5.0 (25)

Private Tour of Palazzo Pitti with Boboli Garden

Vieni a visitare l’ultima residenza dei Medici a Firenze con una guida locale privata. Il museo si svolge attraverso la vita quotidiana della famiglia dei...

1 hour 30 minutes Free Cancellation

5.0 (25)

from
$96

E-bike Chianti Classico Tuscany Tour with Wine and Lunch at Farm

This E-bike Chianti & Tuscany tour in the famous Chianti Classico countryside will take you away from the crowds and noise of Florence, learn about …More

Florence, Italy

5.0 (56)

E-bike Chianti Classico Tuscany Tour with Wine and Lunch at Farm

This E-bike Chianti & Tuscany tour in the famous Chianti Classico countryside will take you away from the crowds and noise of Florence, learn about...

7 hours Free Cancellation

5.0 (56)

from
$181

Small group Chianti-side wine tour with Mercedes V class Van

Our tour is made with passion by expert english speaking drivers who know everything about the area. We will visit two not "commercial" wineries, with …More

Florence, Italy

5.0 (43)

Small group Chianti-side wine tour with Mercedes V class Van

Our tour is made with passion by expert english speaking drivers who know everything about the area. We will visit two not "commercial" wineries, with...

5 hours Free Cancellation

5.0 (43)

from
$276

Hot Air Balloon Flight Over Tuscany from Siena

Admire the stunning landscapes of Tuscany from above on an approximately 1-hour hot air balloon flight over the hills of Siena. This is both a …More

Siena, Italy

5.0 (129)

Hot Air Balloon Flight Over Tuscany from Siena

Admire the stunning landscapes of Tuscany from above on an approximately 1-hour hot air balloon flight over the hills of Siena. This is both a...

3 hours Free Cancellation

5.0 (129)

from
$352

Cinque Terre Small Group Day Tour from Montecatini

Enjoy convenient roundtrip shuttle service with pick-up and drop-off right at your hotel, making your travel easy and stress-free. Your tour leader will pick you …More

Montecatini Terme, Italy

4.8 (49)

Cinque Terre Small Group Day Tour from Montecatini

Enjoy convenient roundtrip shuttle service with pick-up and drop-off right at your hotel, making your travel easy and stress-free. Your tour leader will pick you...

10 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (49)

from
$165

Horseback Ride, visit S.Gimignano, Lunch wine Tasting &much more

Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will give you the …More

Florence, Italy

4.9 (477)

Horseback Ride, visit S.Gimignano, Lunch wine Tasting &much more

Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will give you the...

7 hours Free Cancellation

4.9 (477)

from
$217

Private Tour: Chianti Region Tour by Minivan

Escape from the city traffic to enjoy a lovely day in the Chianti wine region with stop in a small winery for lunch and wine …More

Florence, Italy

5.0 (25)

Private Tour: Chianti Region Tour by Minivan

Escape from the city traffic to enjoy a lovely day in the Chianti wine region with stop in a small winery for lunch and wine...

8 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$848

The balloon flight is magical, it is the dream of adults and children, and it is even more magical to do it in Tuscany and …More

Florence, Italy

5.0 (59)

Hot-Air balloon Ride above Florence

The balloon flight is magical, it is the dream of adults and children, and it is even more magical to do it in Tuscany and...

3 hours Free Cancellation

5.0 (59)

from
$512

E-Bike Tour fortresses and mountains near the Free Baths of Saturnia

This tour is designed to enjoy the Tuscan panoramas away from mass tourism. It is a mixed route, asphalt and dirt, which allows you to …More

5.0 (17)

E-Bike Tour fortresses and mountains near the Free Baths of Saturnia

This tour is designed to enjoy the Tuscan panoramas away from mass tourism. It is a mixed route, asphalt and dirt, which allows you to...

3 to 4 hours Free Cancellation

5.0 (17)

from
$74

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards …More

Siena, Italy

4.5 (125)

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards...

11 hours Free Cancellation

4.5 (125)

from
$177

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

Embark on a captivating journey from Florence to discover Tuscany’s most iconic gems. Begin in Cortona, a hilltop village of Etruscan origin made famous by …More

Florence, Italy

5.0 (41)

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

Embark on a captivating journey from Florence to discover Tuscany’s most iconic gems. Begin in Cortona, a hilltop village of Etruscan origin made famous by...

11 hours Free Cancellation

5.0 (41)

from
$178

Vintage Fiat 500 Tour: Lunch and 2 Wine tastings in the Chianti

Experience Chianti like a true Italian icon. Sit back and relax as your professional private driver takes you through the most scenic roads around Chianti …More

San Gimignano, Italy

4.6 (38)

Vintage Fiat 500 Tour: Lunch and 2 Wine tastings in the Chianti

Experience Chianti like a true Italian icon. Sit back and relax as your professional private driver takes you through the most scenic roads around Chianti...

7 hours Free Cancellation

4.6 (38)

from
$170

Siena: Chianti Wine Tour with Wine Tasting and Lunch

Just a few minutes from Siena, San Giorgio a Lapi offers an authentic experience in the heart of Tuscany, in a unique location between Chianti …More

Siena, Italy

5.0 (20)

Siena: Chianti Wine Tour with Wine Tasting and Lunch

Just a few minutes from Siena, San Giorgio a Lapi offers an authentic experience in the heart of Tuscany, in a unique location between Chianti...

3 hours Free Cancellation

5.0 (20)

from
$85

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?