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 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 →

Motor Valley from Florence: Ducati, Lambo, Pagani & Ferrari

Discover the most iconic museums of Italy’s legendary luxury and sports car brands in a full-day immersive experience, combining automotive excellence with the pleasures of …More

Florence, Italy

5.0 (2)

Motor Valley from Florence: Ducati, Lambo, Pagani & Ferrari

Discover the most iconic museums of Italy’s legendary luxury and sports car brands in a full-day immersive experience, combining automotive excellence with the pleasures of...

10 to 11 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$446

From Florence: Private Pisa, San Gimignano & Wine Lunch

Visit the Leaning Tower of Pisa and the countryside of San Gimignano in one private day, with a genuine farm lunch and local wines, in …More

Florence, Italy

5.0 (2)

From Florence: Private Pisa, San Gimignano & Wine Lunch

Visit the Leaning Tower of Pisa and the countryside of San Gimignano in one private day, with a genuine farm lunch and local wines, in...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$250

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small …More

Siena, Italy

5.0 (35)

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small...

8 hours Hotel pickup offered

5.0 (35)

from
$194

From Siena: Private Volterra, San Gimignano & Wine Lunch

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at …More

Siena, Italy

5.0 (4)

From Siena: Private Volterra, San Gimignano & Wine Lunch

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at...

8 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$272

From Florence: Private Volterra, San Gimignano & Wine Lunch

A private day from Florence to two of the most beautiful hill towns of Tuscany, with a wine lunch at a family-run farm. • Pick-up …More

Florence, Italy

5.0 (2)

From Florence: Private Volterra, San Gimignano & Wine Lunch

A private day from Florence to two of the most beautiful hill towns of Tuscany, with a wine lunch at a family-run farm. • Pick-up...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$261

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
$250

Chianti Wine and Vinci half day Small Group Tour from Lucca

Experience a relaxed afternoon in the Chianti area with a visit to a boutique winery and enjoy a guided Chianti wine tasting along with a …More

Lucca, Italy

5.0 (25)

Chianti Wine and Vinci half day Small Group Tour from Lucca

Experience a relaxed afternoon in the Chianti area with a visit to a boutique winery and enjoy a guided Chianti wine tasting along with a...

5 hours 30 minutes Free Cancellation

5.0 (25)

from
$147

Private Tuscan meal with Wine and EVO oil tasting

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia …More

San Gimignano, Italy

4.9 (35)

Private Tuscan meal with Wine and EVO oil tasting

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia...

1 hour 30 minutes Free Cancellation

4.9 (35)

from
$78

Exclusive Wine Tour and Tasting Experience in Siena

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and …More

Siena, Italy

5.0 (19)

Exclusive Wine Tour and Tasting Experience in Siena

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and...

3 hours 30 minutes Free Cancellation

5.0 (19)

from
$171

Heart of Chianti Classico - 2 Wineries Lunch included - Chianti Wine Tour

Heart of Chianti Classico - 2 Wineries and Lunch - Chianti Wine Tour Tour Length: 7/8 hours. Dates: Every season. Departure Point: From your accommodation …More

Florence, Italy

5.0 (34)

Heart of Chianti Classico - 2 Wineries Lunch included - Chianti Wine Tour

Heart of Chianti Classico - 2 Wineries and Lunch - Chianti Wine Tour Tour Length: 7/8 hours. Dates: Every season. Departure Point: From your accommodation...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (34)

from
$320

Chianti Wine Tour - Private Wine experience in Tuscany Countryside

Dive into an unparalleled wine journey with our exclusive Chianti Wine Tour, starting directly from your accommodation. Onboard our luxury vehicles, driven by an experienced …More

Florence, Italy

5.0 (34)

Chianti Wine Tour - Private Wine experience in Tuscany Countryside

Dive into an unparalleled wine journey with our exclusive Chianti Wine Tour, starting directly from your accommodation. Onboard our luxury vehicles, driven by an experienced...

8 hours Hotel pickup offered Free Cancellation

5.0 (34)

from
$341

Chianti Wine and Vinci half day Small Group Tour from Montecatini Terme

Experience a relaxed afternoon in the Chianti area with a special visit to a boutique winery. Enjoy our guided Chianti Wine tasting and a visit …More

Montecatini Terme, Italy

5.0 (34)

Chianti Wine and Vinci half day Small Group Tour from Montecatini Terme

Experience a relaxed afternoon in the Chianti area with a special visit to a boutique winery. Enjoy our guided Chianti Wine tasting and a visit...

4 hours 30 minutes Free Cancellation

5.0 (34)

from
$136

Private Wine and Extra Virgin Olive Oil Tasting

Escape to a charming family farm and immerse yourself in the authentic flavors of Tuscany. Just a short walk from San Gimignano’s historic center, this …More

San Gimignano, Italy

4.8 (21)

Private Wine and Extra Virgin Olive Oil Tasting

Escape to a charming family farm and immerse yourself in the authentic flavors of Tuscany. Just a short walk from San Gimignano’s historic center, this...

45 minutes Free Cancellation

4.8 (21)

from
$48

Small-Group Vernaccia di San Gimignano Wine Tour - White and Red Wines

This tour takes you to visit two wine region of Tuscany famous for red and white wines. We will make a stop at San Gimignano …More

Florence, Italy

4.8 (22)

Small-Group Vernaccia di San Gimignano Wine Tour - White and Red Wines

This tour takes you to visit two wine region of Tuscany famous for red and white wines. We will make a stop at San Gimignano...

7 hours

4.8 (22)

from
$325

San Gimignano, Saffron and Vernaccia Wine from Florence

The tour starts everyday from Florence (from Siena only on request) at around 9.30 and ends at around 4.30 pm Vernaccia di San Gimignano Wine …More

Florence, Italy

5.0 (6)

San Gimignano, Saffron and Vernaccia Wine from Florence

The tour starts everyday from Florence (from Siena only on request) at around 9.30 and ends at around 4.30 pm Vernaccia di San Gimignano Wine...

8 hours Free Cancellation

5.0 (6)

from
$215

The Essence of Tuscany: Private Chianti & Estate Winery Lunch

Join our highest-rated private escape into the Tuscan countryside. Discover the charm of a medieval hilltop town of your choice and enjoy a legendary, family-style …More

Florence, Italy

4.9 (8)

The Essence of Tuscany: Private Chianti & Estate Winery Lunch

Join our highest-rated private escape into the Tuscan countryside. Discover the charm of a medieval hilltop town of your choice and enjoy a legendary, family-style...

5 hours Hotel pickup offered Free Cancellation

4.9 (8)

from
$369

Tuscany Organic Wine Tour at a Family-Run Winery

Discover authentic Tuscany with a guided wine tour at Podere Pellicciano, a family-run organic winery located in the hills of San Miniato, between Florence and …More

Pisa, Italy

5.0 (22)

Tuscany Organic Wine Tour at a Family-Run Winery

Discover authentic Tuscany with a guided wine tour at Podere Pellicciano, a family-run organic winery located in the hills of San Miniato, between Florence and...

2 to 3 hours Free Cancellation

5.0 (22)

from
$80

Quad Tour ATV Adventure in Chianti. Lunch and Wine Tasting

Come and discover the wild heart of Chianti, together with us you can live an experience totally immersed in the green of the countryside and …More

Florence, Italy

5.0 (35)

Quad Tour ATV Adventure in Chianti. Lunch and Wine Tasting

Come and discover the wild heart of Chianti, together with us you can live an experience totally immersed in the green of the countryside and...

6 to 8 hours Free Cancellation

5.0 (35)

from
$367

From Florence: Half-Day Chianti Wine Tasting & San Gimignano

A light half day in the Chianti hills, perfect if you want a taste of Tuscany and still have half of your day free in …More

Florence, Italy

5.0 (4)

From Florence: Half-Day Chianti Wine Tasting & San Gimignano

A light half day in the Chianti hills, perfect if you want a taste of Tuscany and still have half of your day free in...

5 hours Free Cancellation

5.0 (4)

from
$91

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 (11)

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 (11)

from
$129

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?