Top Italy Wine Tasting & Winery Tours

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We sure do. Check out our curated lists of hand-picked Italy Tours. Top 10 Italy 2026 Senior-friendly tours Italy The best tours and activities for culture lovers in Italy Top Day Trips from Italy Things to do in Italy this summer View all Italy Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Italy?

Based on our sales data over the past year, the most popular styles of tours and activities in Italy are: Italy Luxury & Special Occasions Italy Luxury Tours Italy Tours & Sightseeing Italy Cultural & Theme Tours Italy Walking & Biking Tours View all tour styles in Italy →

8 Days Tuscan Food and Wine Experience Shared Tour

Tuscany is one of the great food and wine destinations in Italy, and, indeed the world. The scenery is unbelievably beautiful with large tracts of …More

Siena, Italy

8 Days Tuscan Food and Wine Experience Shared Tour

Tuscany is one of the great food and wine destinations in Italy, and, indeed the world. The scenery is unbelievably beautiful with large tracts of...

8 days

from
$5,250

"A journey into the heart of Tuscany: 5 wines, 5 stories" Imagine embarking on a journey through the rolling Tuscan hills, where each village holds …More

Florence, Italy

Wine tasting in Florence

"A journey into the heart of Tuscany: 5 wines, 5 stories" Imagine embarking on a journey through the rolling Tuscan hills, where each village holds...

1 hour 20 minutes Free Cancellation

from
$91

Questo tour privato offre un modo confortevole e personalizzato per esplorare i punti salienti di Pisa, combinando la storia monumentale con le delizie enogastronomiche della …More

Tour privato di Pisa e wine tasting dal Porto di Livorno

Questo tour privato offre un modo confortevole e personalizzato per esplorare i punti salienti di Pisa, combinando la storia monumentale con le delizie enogastronomiche della...

8 hours Free Cancellation

from
$1,068

Siena and Chianti Castle with Lunch&WineTasting from Florence

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: …More

Florence, Italy

Siena and Chianti Castle with Lunch&WineTasting from Florence

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer:...

9 hours Hotel pickup offered

from
$738

Chianti / San Gimignano / Siena-Tour in Ferrari

Driving the Ferrari Spider in Tuscany, in the Chianti area is pure magic .. In Chianti there are the most beautiful roads in Europe, full …More

Florence, Italy

Chianti / San Gimignano / Siena-Tour in Ferrari

Driving the Ferrari Spider in Tuscany, in the Chianti area is pure magic .. In Chianti there are the most beautiful roads in Europe, full...

7 to 8 hours Hotel pickup offered

from
$3,674

San Gimignano and Chianti Winery from Lucca

FULL DAY PRIVATE TOUR with LIMOSERVICEINITALY! On this tour we will take you to the medieval town of San Gimignano, definitely one of the most …More

Lucca, Italy

San Gimignano and Chianti Winery from Lucca

FULL DAY PRIVATE TOUR with LIMOSERVICEINITALY! On this tour we will take you to the medieval town of San Gimignano, definitely one of the most...

8 hours Hotel pickup offered

from
$1,118

Lake Maggiore exclusive: Isola Bella open only for you at sunset

The sunset on lake Maggiore paints the mountains around of amazing shades and fires up the water; at this time of the day, the blooming …More

Lake Maggiore, Italy

Lake Maggiore exclusive: Isola Bella open only for you at sunset

The sunset on lake Maggiore paints the mountains around of amazing shades and fires up the water; at this time of the day, the blooming...

2 hours

from
$2,412

Siena and Chianti Countryside Lunch & 2WineTastings from Florence

Enjoy this unforgettable High Level Tour and delve into Tuscany’s history and culture on a full-day private tour of Siena and Chianti Wine area. Depart …More

Florence, Italy

Siena and Chianti Countryside Lunch & 2WineTastings from Florence

Enjoy this unforgettable High Level Tour and delve into Tuscany’s history and culture on a full-day private tour of Siena and Chianti Wine area. Depart...

10 hours Hotel pickup offered

from
$685

4-Days Wonderful Piedmont Tour from Milan

4 days and 3 nights leaving from Milan. Small groups tour discovering the region of the great Italian wines, the history of the unification of …More

Milan, Italy

4-Days Wonderful Piedmont Tour from Milan

4 days and 3 nights leaving from Milan. Small groups tour discovering the region of the great Italian wines, the history of the unification of...

4 days

from
$1,963

Brunello Montalcino Nobile Montepulciano 2 wineries Val d'Orcia

This will be a wonderful day that you will remember for all your life, Val D'Orcia is a magic place from a spectacular views, sitting …More

Florence, Italy

Brunello Montalcino Nobile Montepulciano 2 wineries Val d'Orcia

This will be a wonderful day that you will remember for all your life, Val D'Orcia is a magic place from a spectacular views, sitting...

9 hours Hotel pickup offered Free Cancellation

from
$1,263

Siena with lunch and wines tasting on Chianti's exclusive vinery

A full experience in Tuscany, the medioeval city of Siena for 2 hours free to walk around the city and after a fantastic experience on …More

Florence, Italy

Siena with lunch and wines tasting on Chianti's exclusive vinery

A full experience in Tuscany, the medioeval city of Siena for 2 hours free to walk around the city and after a fantastic experience on...

7 hours Hotel pickup offered Free Cancellation

from
$1,366

Proposals and Romantic Experiences in Tuscany

Do you want to surprise the person you love with a very special, romantic evening? Or else do you who want to impress your loved …More

Florence, Italy

Proposals and Romantic Experiences in Tuscany

Do you want to surprise the person you love with a very special, romantic evening? Or else do you who want to impress your loved...

4 hours Hotel pickup offered

from
$1,263

From Como to Lugano: Art and Tastings Experience

Lugano, the elegant capital of Canton Ticino, blends Swiss precision with Italian flair, where art, landscape, and culinary traditions harmoniously meet. Departing from Como, this …More

Lake Como, Italy

From Como to Lugano: Art and Tastings Experience

Lugano, the elegant capital of Canton Ticino, blends Swiss precision with Italian flair, where art, landscape, and culinary traditions harmoniously meet. Departing from Como, this...

5 hours Hotel pickup offered

from
$483

Full-Day Private Tour Truffles Lovers Experience with Lunch

A unique and different day from the usual standard tour for tourists. This excursion is very special. You will appreciate it. it is ideal for …More

Salerno, Italy

Full-Day Private Tour Truffles Lovers Experience with Lunch

A unique and different day from the usual standard tour for tourists. This excursion is very special. You will appreciate it. it is ideal for...

10 hours Hotel pickup offered Free Cancellation

from
$730

Escape from Florence to Cortona: 5-Star Hotel, Tours, Activities

Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Florence. Come and savor the very best of the …More

Florence, Italy

Escape from Florence to Cortona: 5-Star Hotel, Tours, Activities

Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Florence. Come and savor the very best of the...

4 days

from
$2,793

Montepulciano noble wines tour in Tuscany from Rome

A visit to Montepulciano and Pienza offers an extraordinary experience to discover the culture, history and food and wine of the region. Montepulciano is famous …More

Rome, Italy

Montepulciano noble wines tour in Tuscany from Rome

A visit to Montepulciano and Pienza offers an extraordinary experience to discover the culture, history and food and wine of the region. Montepulciano is famous...

10 hours Hotel pickup offered Free Cancellation

from
$1,484

Tuscany Multi day eBike tour Wine and Pasta

Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Rome. Come and savor the very best of the …More

Arezzo, Italy

Tuscany Multi day eBike tour Wine and Pasta

Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Rome. Come and savor the very best of the...

4 days

from
$2,827

Exclusive Pickleball Experience – Play pickleball in stunning Italian locations with local and international players. Whether you're a beginner or a pro! Blend of Sport …More

Palermo, Italy

Pickleball & Vacation in Italy

Exclusive Pickleball Experience – Play pickleball in stunning Italian locations with local and international players. Whether you're a beginner or a pro! Blend of Sport...

6 days

from
$3,469

Private Tour From Rome To Pompeii Excavations History Volcanoes And Wine

Are you ready for an unforgettable adventure? Join our guided tour from Rome to discover the wonders of Pompeii and Vesuvius! Explore the fascinating archaeological …More

Rome, Italy

Private Tour From Rome To Pompeii Excavations History Volcanoes And Wine

Are you ready for an unforgettable adventure? Join our guided tour from Rome to discover the wonders of Pompeii and Vesuvius! Explore the fascinating archaeological...

10 hours Hotel pickup offered Free Cancellation

from
$913

From Verona to Valpolicella: Romance, Villages and Fine Wines

Just beyond Verona, the city of eternal love, lies Valpolicella, a land of undulating vineyards, timeless villages and wines rich in history and character. Your …More

Verona, Italy

From Verona to Valpolicella: Romance, Villages and Fine Wines

Just beyond Verona, the city of eternal love, lies Valpolicella, a land of undulating vineyards, timeless villages and wines rich in history and character. Your...

8 hours

from
$433

Frequently Asked Questions

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

What are the best kid-friendly options for Italy Wine Tasting & Winery Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Italy Wine Tasting & Winery Tours are:

View all kid-friendly Tours →

Which Italy Wine Tasting & Winery Tours have Instant Confirmation?

Italy Wine Tasting & Winery Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Italy Wine Tasting & Winery Tours have Free Cancellation?

Italy Wine Tasting & Winery Tours 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 Italy Wine Tasting & Winery Tours have Hotel Pickup?

No problem. These Italy Wine Tasting & Winery Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Italy trip ideas?

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