Top Italy Wine Tasting & Winery Tours

Q: I need a ride! Which Italy Wine Tasting & Winery Tours have Hotel Pickup?

No problem. These Italy Wine Tasting & Winery Tours include Hotel Pickup: Sorrento Farm by Tuk Tuk: Cheese, Limoncello & Hands-On Pizza Private 6-Hour Tour of Three Etna Wineries with food&wine tasting Olive oil tasting in Sorrento Tour Etna and Wine Tasting Mt Etna and Wine tasting tour from Catania View all Tours with Hotel Pickup →

Q: Got any more Italy trip ideas?

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 →

Rich aperitif 5 wines and walk in the vineyards

Don't miss the opportunity to enjoy a walk in the Vineyard of Assisi and taste SAIO Assisi wines paired with exclusively local and handmade food …More

Assisi, Italy

4.8 (29)

Rich aperitif 5 wines and walk in the vineyards

Don't miss the opportunity to enjoy a walk in the Vineyard of Assisi and taste SAIO Assisi wines paired with exclusively local and handmade food...

1 hour 30 minutes Free Cancellation

4.8 (29)

from
$28

Private Pisa and Lucca Wine Tour from Florence

Leave Florence and discover the Tuscan cities of Lucca and Pisa on a day trip. You’ll see the UNESCO-listed Leaning Tower of Pisa (entry own …More

Florence, Italy

4.8 (29)

Private Pisa and Lucca Wine Tour from Florence

Leave Florence and discover the Tuscan cities of Lucca and Pisa on a day trip. You’ll see the UNESCO-listed Leaning Tower of Pisa (entry own...

8 hours Free Cancellation

4.8 (29)

from
$201

Private Chianti Classico Experience from Florence

Do you want to learn more about one of the most prestigious wines in Italy and worldwide? Embark with us on this journey in the …More

Florence, Italy

5.0 (29)

Private Chianti Classico Experience from Florence

Do you want to learn more about one of the most prestigious wines in Italy and worldwide? Embark with us on this journey in the...

10 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$536

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
$141

Visit to the Cellar with Wine & Food Tasting over the Val d'Orcia

Discover the Podere Montale Winery with an exclusive experience, guided by an expert wine connoisseur. Visit the vineyard where Sangiovese grapes grow, then continuing to …More

4.9 (29)

Visit to the Cellar with Wine & Food Tasting over the Val d'Orcia

Discover the Podere Montale Winery with an exclusive experience, guided by an expert wine connoisseur. Visit the vineyard where Sangiovese grapes grow, then continuing to...

2 hours Free Cancellation

4.9 (29)

from
$68

Scenic Horseback Ride, Wine Tasting & Lunch on Mt. Vesuvius

Discover the perfect blend of adventure, culture, and cuisine in this exclusive full-day experience. Begin with a scenic horseback ride through Vesuvius's volcanic landscapes, where …More

Pompeii, Italy

5.0 (29)

Scenic Horseback Ride, Wine Tasting & Lunch on Mt. Vesuvius

Discover the perfect blend of adventure, culture, and cuisine in this exclusive full-day experience. Begin with a scenic horseback ride through Vesuvius's volcanic landscapes, where...

4 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$148

From Messina Cruise Terminal: Private Godfather tour + Lunch

Private tour from Messina by comfortable air-conditioned car with a personal local guide to the must-see Sicilian hilltop villages that have become world-known thanks to …More

Messina, Italy

4.8 (29)

From Messina Cruise Terminal: Private Godfather tour + Lunch

Private tour from Messina by comfortable air-conditioned car with a personal local guide to the must-see Sicilian hilltop villages that have become world-known thanks to...

5 to 9 hours Free Cancellation

4.8 (29)

from
$284

Tuscany Wine Tour: 2 Wineries & San Gimignano from Rome

Take a full day trip from Rome to explore Tuscany, enjoy two wineries, amazing scenery, visit to the famous Medieval town of San Gimignano and …More

Rome, Italy

4.9 (28)

Tuscany Wine Tour: 2 Wineries & San Gimignano from Rome

Take a full day trip from Rome to explore Tuscany, enjoy two wineries, amazing scenery, visit to the famous Medieval town of San Gimignano and...

12 hours Free Cancellation

4.9 (28)

from
$226

Parmigiano Cheese Factory Visit and Tasting

Visit a Parmigiano Reggiano dairy and immerse yourself in the traditional cheese-making process, witnessing the artisanal craftsmanship behind this world-renowned cheese, from fresh milk to …More

Parma, Italy

4.9 (28)

Parmigiano Cheese Factory Visit and Tasting

Visit a Parmigiano Reggiano dairy and immerse yourself in the traditional cheese-making process, witnessing the artisanal craftsmanship behind this world-renowned cheese, from fresh milk to...

2 to 3 hours Free Cancellation

4.9 (28)

from
$92

Sunset Boat Tour with Aperitif in Portofino

Immerse yourself in an unforgettable boat trip through crystal clear waters, where every wave tells a story and every bay hides a treasure. Enjoy the …More

Portofino, Italy

4.9 (28)

Sunset Boat Tour with Aperitif in Portofino

Immerse yourself in an unforgettable boat trip through crystal clear waters, where every wave tells a story and every bay hides a treasure. Enjoy the...

1 hour 30 minutes Free Cancellation

4.9 (28)

from
$86

Organic Wine Tasting with Panoramic Chianti Classico Views

Exceptional Organic Wines: Sip your way through a guided tasting of our acclaimed organic Chianti Classico and Supertuscan wines, hosted by our friendly wine experts. …More

San Gimignano, Italy

4.8 (28)

Organic Wine Tasting with Panoramic Chianti Classico Views

Exceptional Organic Wines: Sip your way through a guided tasting of our acclaimed organic Chianti Classico and Supertuscan wines, hosted by our friendly wine experts....

1 hour 15 minutes Free Cancellation

4.8 (28)

from
$40

Roman Countryside: Wine and Food Tasting, Semi-Private Day Tour

Discover the enchanting Roman countryside on this unforgettable day trip to the Castelli Romani, a hidden gem just outside Rome. Travel from your hotel along …More

Rome, Italy

4.8 (28)

Roman Countryside: Wine and Food Tasting, Semi-Private Day Tour

Discover the enchanting Roman countryside on this unforgettable day trip to the Castelli Romani, a hidden gem just outside Rome. Travel from your hotel along...

6 hours Hotel pickup offered Free Cancellation

4.8 (28)

from
$192

Modena: Discover the Food, Market & City Highlights Tour

Join us for a flavorful journey through Modena, where history and cuisine come together. Start in Piazza Grande, exploring its iconic landmarks, including the Cathedral, …More

Modena, Italy

5.0 (28)

Modena: Discover the Food, Market & City Highlights Tour

Join us for a flavorful journey through Modena, where history and cuisine come together. Start in Piazza Grande, exploring its iconic landmarks, including the Cathedral,...

2 hours 30 minutes Free Cancellation

5.0 (28)

from
$89

Private Syracuse -Archaeological Park and Ortigia with Arancino

Take a 4-5 hr private tour to Syracuse's Neapolis Archaeological park, UNESCO world heritage, and historical center of the city - Ortigia, one of the …More

Syracuse, Italy

4.8 (28)

Private Syracuse -Archaeological Park and Ortigia with Arancino

Take a 4-5 hr private tour to Syracuse's Neapolis Archaeological park, UNESCO world heritage, and historical center of the city - Ortigia, one of the...

4 hours Hotel pickup offered Free Cancellation

4.8 (28)

from
$238

A licensed sommelier, will always be by your side as your driver and guide to share his knowledge and help you discover the best of …More

Siena, Italy

5.0 (28)

Discover Brunello Wines

A licensed sommelier, will always be by your side as your driver and guide to share his knowledge and help you discover the best of...

8 hours

5.0 (28)

from
$281

Savor Ossola Wines & Local Treats in a Scenic Vineyard

Discover the unique flavors of Valli Ossolane, a hidden gem in the Piedmont wine scene, recognized with DOC status in 2009. Nestled in the breathtaking …More

Lake Maggiore, Italy

4.9 (27)

Savor Ossola Wines & Local Treats in a Scenic Vineyard

Discover the unique flavors of Valli Ossolane, a hidden gem in the Piedmont wine scene, recognized with DOC status in 2009. Nestled in the breathtaking...

2 hours Free Cancellation

4.9 (27)

from
$38

Embark on a truffle hunting adventure with an Italian Tartufaro and the dog. Discover the land of Valpolicella and join the scorzone Truffle hunt. The …More

Verona, Italy

4.9 (27)

Truffle Hunting with Wine Tasting

Embark on a truffle hunting adventure with an Italian Tartufaro and the dog. Discover the land of Valpolicella and join the scorzone Truffle hunt. The...

2 hours 30 minutes Free Cancellation

4.9 (27)

from
$182

Best of Tuscany: Full Day Private Tour to Val D'Orcia

Experience the charm of Tuscany on a private tour led by a local expert. Wander through the stunning UNESCO-listed Val d'Orcia, where every road is …More

Florence, Italy

4.9 (27)

Best of Tuscany: Full Day Private Tour to Val D'Orcia

Experience the charm of Tuscany on a private tour led by a local expert. Wander through the stunning UNESCO-listed Val d'Orcia, where every road is...

8 hours Hotel pickup offered Free Cancellation

4.9 (27)

from
$339

If you want always to understand how to recognize an high quality extra virgin olive oil: this is the tour for you! You will visit …More

Assisi, Italy

4.9 (27)

Apprentice Olive Oil taster for a day!

If you want always to understand how to recognize an high quality extra virgin olive oil: this is the tour for you! You will visit...

1 hour Free Cancellation

4.9 (27)

from
$56

Venice Like a Local Wine and Cicchetti at Liuba and Hugo's House

Spend an evening in a Venetian house with Liuba, sommelier, and Hugo, Pro chef. In a small group of a maximum of six people, you …More

Venice, Italy

5.0 (27)

Venice Like a Local Wine and Cicchetti at Liuba and Hugo's House

Spend an evening in a Venetian house with Liuba, sommelier, and Hugo, Pro chef. In a small group of a maximum of six people, you...

2 hours 30 minutes Free Cancellation

5.0 (27)

from
$97

Frequently Asked Questions

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

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

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?

Got any more Italy trip ideas?

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