Top Tuscany Wine Tasting & Winery Tours

Q: Which Tuscany Wine Tasting & Winery Tours have Instant Confirmation?

Tuscany Wine Tasting & Winery Tours with Instant Confirmation include: Three Days Tuscany Winery Tour from Florence 3-Day Tuscany Wine Tour Experience from Florence Tuscany Private Guided Wine Tasting Tour by Car Private Tour Of Chianti with Wine Tastings Florence to Ferrari Museum then lunch in a Medieval Castle View all Tours with Instant Confirmation →

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

No problem. These Tuscany Wine Tasting & Winery Tours include Hotel Pickup: Three Days Tuscany Winery Tour from Florence Bolgheri / Volterra / Florence-Tour in Ferrari Chianti / San Gimignano / Siena-Tour in Ferrari Brunello/Montalcino-Tour in Ferrari Elopement in Florence and Tuscany 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 →

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

Three Days Tuscany Winery Tour from Florence

Embark on an Unforgettable Wine Tour in Tuscany! Welcome to the heart of Italian wine country, where rolling vineyards, centuries-old wineries, and exceptional vintages await …More

Florence, Italy

Three Days Tuscany Winery Tour from Florence

Embark on an Unforgettable Wine Tour in Tuscany! Welcome to the heart of Italian wine country, where rolling vineyards, centuries-old wineries, and exceptional vintages await...

3 days Hotel pickup offered Free Cancellation

from
$4,810

Bolgheri / Volterra / Florence-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

5.0 (1)

Bolgheri / Volterra / Florence-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...

6 hours Hotel pickup offered

5.0 (1)

from
$4,477

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

Private 5 Days Italy Tuscany Discovery from Florence

This is a private Italy family tour, which allow you to experience culture of Florence. Furthermore, you guide will take you to explore world famous …More

Florence, Italy

Private 5 Days Italy Tuscany Discovery from Florence

This is a private Italy family tour, which allow you to experience culture of Florence. Furthermore, you guide will take you to explore world famous...

5 days

from
$3,419

Driving the Ferrari California Turbo Cabriolet in Tuscany, in the heart of Val D'Orcia Valley "Unescu Heritage of theWorld" is pure magic .. Your Tour …More

Siena, Italy

Brunello/Montalcino-Tour in Ferrari

Driving the Ferrari California Turbo Cabriolet in Tuscany, in the heart of Val D'Orcia Valley "Unescu Heritage of theWorld" is pure magic .. Your Tour...

4 hours Hotel pickup offered

from
$3,329

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

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

3-Day Tuscany Wine Tour Experience from Florence

Get picked up at your accommodation to experience a three-day full immersion Wine Tour and stay in a private Villa situated in a conventional cosy Tuscan …More

Florence, Italy

5.0 (3)

3-Day Tuscany Wine Tour Experience from Florence

Get picked up at your accommodation to experience a three-day full immersion Wine Tour and stay in a private Villa situated in a conventional cosy Tuscan...

3 days

5.0 (3)

from
$2,488

Elopement represents for many a way to get married focusing exclusively on themselves as a couple and live an intimate wedding experience. We at Your …More

Florence, Italy

Elopement in Florence and Tuscany

Elopement represents for many a way to get married focusing exclusively on themselves as a couple and live an intimate wedding experience. We at Your...

1 day Hotel pickup offered

from
$2,270

Tuscany Private Guided Wine Tasting Tour by Car

Explore the picturesque landscapes of Tuscany on a captivating day trip from Florence. This intimate journey invites you to savor the rich flavors of Brunello …More

Livorno, Italy

5.0 (2)

Tuscany Private Guided Wine Tasting Tour by Car

Explore the picturesque landscapes of Tuscany on a captivating day trip from Florence. This intimate journey invites you to savor the rich flavors of Brunello...

10 hours Free Cancellation

5.0 (2)

from
$1,825

Private Tour Of Chianti with Wine Tastings

Spend a unique day in the Tuscan countryside and discover the essence of our region: delicious wine and food, breathtaking views, medieval castles, and unrivaled …More

Florence, Italy

5.0 (1)

Private Tour Of Chianti with Wine Tastings

Spend a unique day in the Tuscan countryside and discover the essence of our region: delicious wine and food, breathtaking views, medieval castles, and unrivaled...

8 hours Hotel pickup offered

5.0 (1)

from
$1,704

Private driver from Florence: Siena, San Gimignano, Pisa 12 hours

A long intense day where we will see the main city of Tuscany: Pisa, San Gimignano & Siena. Learn about it's history, culture and heritage. …More

Florence, Italy

5.0 (2)

Private driver from Florence: Siena, San Gimignano, Pisa 12 hours

A long intense day where we will see the main city of Tuscany: Pisa, San Gimignano & Siena. Learn about it's history, culture and heritage....

12 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,630

Florence to Ferrari Museum then lunch in a Medieval Castle

Departing from your Florence accommodation we drive to Maranello, the Ferrari museum town. Visit of Ferrari museum (to be reserved in advance-not included) then after …More

Florence, Italy

5.0 (1)

Florence to Ferrari Museum then lunch in a Medieval Castle

Departing from your Florence accommodation we drive to Maranello, the Ferrari museum town. Visit of Ferrari museum (to be reserved in advance-not included) then after...

10 hours Free Cancellation

5.0 (1)

from
$1,544

San Gimignano and Siena full day Hire a driver English speaking

Pick up at 9 am in Florence by the Hotel or where is best for the client, drive to San Gimignano (1 Hour), free time …More

Florence, Italy

5.0 (1)

San Gimignano and Siena full day Hire a driver English speaking

Pick up at 9 am in Florence by the Hotel or where is best for the client, drive to San Gimignano (1 Hour), free time...

9 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$1,476

TRANSFER TOUR Florence to Rome with a wine experience in MONTEPULCIANO

It's not just arriving at your destination that makes your vacation ... it's experiencing new and wonderful things along the way. Enjoy a very special …More

Florence, Italy

5.0 (1)

TRANSFER TOUR Florence to Rome with a wine experience in MONTEPULCIANO

It's not just arriving at your destination that makes your vacation ... it's experiencing new and wonderful things along the way. Enjoy a very special...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$1,435

Chianti Private Tour with Dinner and Wine Tasting Experience

Would you like to see one of the greatest and most beautiful areas in Tuscany in one memorable day? Join our tour and spend a …More

Florence, Italy

Chianti Private Tour with Dinner and Wine Tasting Experience

Would you like to see one of the greatest and most beautiful areas in Tuscany in one memorable day? Join our tour and spend a...

6 hours Hotel pickup offered

from
$1,416

Private Wine Tours all inclusive in Chianti Tuscany Lunch & Wine

A wonderful day with many stops for panoramic photos of the beautiful countryside of Chianti, guided from an English speaking professional driver with a comfortable …More

Florence, Italy

Private Wine Tours all inclusive in Chianti Tuscany Lunch & Wine

A wonderful day with many stops for panoramic photos of the beautiful countryside of Chianti, guided from an English speaking professional driver with a comfortable...

6 hours Hotel pickup offered Free Cancellation

from
$1,378

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

Private Day Trip to Montalcino and Montepulciano from Florence

Embark on a 9-hour private tour from Florence to the Tuscan Brunello vineyards, the perfect excursion for the discerning traveler and wine enthusiast. Travel from the …More

Florence, Italy

5.0 (2)

Private Day Trip to Montalcino and Montepulciano from Florence

Embark on a 9-hour private tour from Florence to the Tuscan Brunello vineyards, the perfect excursion for the discerning traveler and wine enthusiast. Travel from the...

9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,362

Frequently Asked Questions

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

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

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

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

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

View all kid-friendly Tours →

Which Tuscany Wine Tasting & Winery Tours have Instant Confirmation?

Which Tuscany Wine Tasting & Winery Tours have Free Cancellation?

Tuscany 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 Tuscany Wine Tasting & Winery Tours have Hotel Pickup?

Got any more Tuscany trip ideas?

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