Top Italy Wine Tasting & Winery Tours

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 →

Wine Tasting in Locorotondo: Discover Apulian Wines

Immerse yourself in the rich flavors of Puglia with a wine tasting experience in Locorotondo. This captivating journey takes place in a charming wine shop, …More

Alberobello & Locorotondo, Italy

3.0 (1)

Wine Tasting in Locorotondo: Discover Apulian Wines

Immerse yourself in the rich flavors of Puglia with a wine tasting experience in Locorotondo. This captivating journey takes place in a charming wine shop,...

1 hour 30 minutes Free Cancellation

3.0 (1)

from
$40

Private 8 hours Tour of Florence and Chianti with wine tasting

Florence is a city full of art, culture, and rich history. There are many sights to see that will leave you in awe. From the …More

Florence, Italy

Private 8 hours Tour of Florence and Chianti with wine tasting

Florence is a city full of art, culture, and rich history. There are many sights to see that will leave you in awe. From the...

8 hours Hotel pickup offered Free Cancellation

from
$289

Private Full-Day Customizable Tour to Bolgheri from Florence

Are you in Florence and you want to visit Bolgheri? To do this we offer our transport service with minivan and expert driver in English …More

Florence, Italy

Private Full-Day Customizable Tour to Bolgheri from Florence

Are you in Florence and you want to visit Bolgheri? To do this we offer our transport service with minivan and expert driver in English...

6 hours Hotel pickup offered

from
$1,078

This 3-night tour expertly designed for the discovery of some of the most famous Italian DOP products such as: Parmiggiano Reggiano, Prosciutto di Parma, Aceto …More

Venice, Italy

From Venice to Florence, 3 days tour

This 3-night tour expertly designed for the discovery of some of the most famous Italian DOP products such as: Parmiggiano Reggiano, Prosciutto di Parma, Aceto...

3 days

from
$1,361

3 Nights Etna Wine and Movie Location Tour Italy with Sicily Food

Beach , Volcano , Godfather , Wine Estate - within a distance of 50 km in Sicily! Content of our 3 nights and 4 days …More

Taormina, Hungary

3 Nights Etna Wine and Movie Location Tour Italy with Sicily Food

Beach , Volcano , Godfather , Wine Estate - within a distance of 50 km in Sicily! Content of our 3 nights and 4 days...

4 days Hotel pickup offered Free Cancellation

from
$1,073

14 Days Private Italy Grand Tour Rome Tuscany Florence Venice

Experience the ultimate 14-Day Private Grand Tour of Italy, a seamless journey through 6 regions of extraordinary beauty — from the timeless icons of Rome …More

Rome, Italy

14 Days Private Italy Grand Tour Rome Tuscany Florence Venice

Experience the ultimate 14-Day Private Grand Tour of Italy, a seamless journey through 6 regions of extraordinary beauty — from the timeless icons of Rome...

14 days Hotel pickup offered

from
$7,061

8 Days Private Tuscany Tour Florence Siena San Gimignano Orvieto

Experience the enchantment of Tuscany and Orvieto on an exclusive 8-day journey of luxury, art and relaxation. Unlike standard group tours, this is a fully …More

Rome, Italy

8 Days Private Tuscany Tour Florence Siena San Gimignano Orvieto

Experience the enchantment of Tuscany and Orvieto on an exclusive 8-day journey of luxury, art and relaxation. Unlike standard group tours, this is a fully...

8 days Hotel pickup offered

from
$4,071

8 Days Tuscany and Umbria Luxury Tour with Private Driver & Guide

Experience Italy in absolute exclusivity. What sets this journey apart is the seamless blend of luxury and expertise: you will enjoy a dedicated private driver …More

Rome, Italy

8 Days Tuscany and Umbria Luxury Tour with Private Driver & Guide

Experience Italy in absolute exclusivity. What sets this journey apart is the seamless blend of luxury and expertise: you will enjoy a dedicated private driver...

8 days Hotel pickup offered

from
$4,133

Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting

On the way from Rome to Siena, you will be fascinated by the splendid landscapes of the Tuscan hills. Sipping a good glass during the …More

Rome, Italy

Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting

On the way from Rome to Siena, you will be fascinated by the splendid landscapes of the Tuscan hills. Sipping a good glass during the...

12 hours Hotel pickup offered Free Cancellation

from
$322

Full-Day Valpolicella Private Tour from Milan with Wine Taste

The Valpolicella, an area which lays north-west of Verona and stretches between Garda, the Lessini Mountains and the Valdadige, offers splendid naturalistic itineraries, immersed in …More

Milan, Italy

Full-Day Valpolicella Private Tour from Milan with Wine Taste

The Valpolicella, an area which lays north-west of Verona and stretches between Garda, the Lessini Mountains and the Valdadige, offers splendid naturalistic itineraries, immersed in...

8 to 9 hours Hotel pickup offered

from
$454

3 Days Tour in Cinema Paradiso Tour and Palermo with Food

Cinema Paradiso & Godfather, Sicilian atmosphere, Palermo! A guided tour + lunch in the pulsating coastal town Cefalù Dinner, 2 nights accommodation in Palermo. Tour …More

Taormina, Italy

3 Days Tour in Cinema Paradiso Tour and Palermo with Food

Cinema Paradiso & Godfather, Sicilian atmosphere, Palermo! A guided tour + lunch in the pulsating coastal town Cefalù Dinner, 2 nights accommodation in Palermo. Tour...

3 days Hotel pickup offered Free Cancellation

from
$1,084

4 Days Tour to Discover the Molise Region

Molise: a place you don't expect! Let our history, nature and food and wine win your heart! Explore Molise. A land where it is possible …More

Rome, Italy

4 Days Tour to Discover the Molise Region

Molise: a place you don't expect! Let our history, nature and food and wine win your heart! Explore Molise. A land where it is possible...

4 days Hotel pickup offered Free Cancellation

from
$3,192

Day trip from Rome: Deluxe wine tasting in Montalcino - private tour

Travel from Rome to Montalcino and visit the Abbey of Sant’Antimo, a former Benedictine monastery surrounded by lush vineyards. Marvel at its Romanesque architecture and …More

Rome, Italy

Day trip from Rome: Deluxe wine tasting in Montalcino - private tour

Travel from Rome to Montalcino and visit the Abbey of Sant’Antimo, a former Benedictine monastery surrounded by lush vineyards. Marvel at its Romanesque architecture and...

12 hours Hotel pickup offered Free Cancellation

from
$608

Day Trip from Florence: Orvieto and Wine tasting in Montepulciano - private tour

Having left the center of Florence, you will drive through the beautiful landscape of Tuscany and Umbria. You will stop in Orvieto and walk on …More

Florence, Italy

Day Trip from Florence: Orvieto and Wine tasting in Montepulciano - private tour

Having left the center of Florence, you will drive through the beautiful landscape of Tuscany and Umbria. You will stop in Orvieto and walk on...

10 hours Hotel pickup offered

from
$435

Siena, San Gimignano and Monteriggioni Wine Tasting and Tour

Uncover the soul of Tuscany on this 8-hour private tour through three of its most iconic towns: Siena, San Gimignano, and Monteriggioni. Travel in style …More

Siena, Italy

Siena, San Gimignano and Monteriggioni Wine Tasting and Tour

Uncover the soul of Tuscany on this 8-hour private tour through three of its most iconic towns: Siena, San Gimignano, and Monteriggioni. Travel in style...

8 hours Free Cancellation

from
$196

Grand 2-Day Tour of Tuscany: Siena, San Gimignano, and Florence

The first day visit Siena and San Gimignano, beautiful medieval cities. In Siena we will visit the monuments and “Piazza del Campo” where the famous …More

Rome, Italy

Grand 2-Day Tour of Tuscany: Siena, San Gimignano, and Florence

The first day visit Siena and San Gimignano, beautiful medieval cities. In Siena we will visit the monuments and “Piazza del Campo” where the famous...

2 days Hotel pickup offered Free Cancellation

from
$1,025

Pompeii SkipTheLine and Mt Vesuvius with Lunch&WineTasting from Rome

A great Private All-Inclusive Fullday from Rome visiting Pompeii Archaeological Park, UNESCO World Heritage Site, and head to Mt. Vesuvius to see the Volcano crater. …More

Rome, Italy

Pompeii SkipTheLine and Mt Vesuvius with Lunch&WineTasting from Rome

A great Private All-Inclusive Fullday from Rome visiting Pompeii Archaeological Park, UNESCO World Heritage Site, and head to Mt. Vesuvius to see the Volcano crater....

12 hours Hotel pickup offered Free Cancellation

from
$459

A great Private All-Inclusive Fullday from Rome visiting Pompeii Archaeological Park, UNESCO World Heritage Site, and head to Mt. Vesuvius to see the Volcano crater. …More

Rome, Italy

Pompeii SkipTheLine and Mt Vesuvius with Lunch&WineTasting from Rome

A great Private All-Inclusive Fullday from Rome visiting Pompeii Archaeological Park, UNESCO World Heritage Site, and head to Mt. Vesuvius to see the Volcano crater....

12 hours Hotel pickup offered Free Cancellation

from
$459

Wild Abruzzo CookingClass and WineTasting from Rome

Experience Authentic Italian Cooking Class in a medieval village in Abruzzo Lands half an hour from Rome. Cooking with Rosa. She will show you a …More

Rome, Italy

Wild Abruzzo CookingClass and WineTasting from Rome

Experience Authentic Italian Cooking Class in a medieval village in Abruzzo Lands half an hour from Rome. Cooking with Rosa. She will show you a...

12 hours Hotel pickup offered Free Cancellation

from
$568

Private Sailing Boat Trip with Educational Wine Tasting

What makes such a boat trip unique is that you get to enjoy the amazing view of Naples from the sea while sailing in the …More

Naples, Italy

Private Sailing Boat Trip with Educational Wine Tasting

What makes such a boat trip unique is that you get to enjoy the amazing view of Naples from the sea while sailing in the...

6 to 7 hours Hotel pickup offered Free Cancellation

from
$1,378

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?

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?