Top Tuscany Wine Tasting & Winery Tours

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 →

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

San Gimignano with lunch and wine tasting on a local winery

A wonderful day visiting the medioeval village of San Gimignano one of the main villages of Tuscany called the medioeval Manhatten because for all his …More

Florence, Italy

San Gimignano with lunch and wine tasting on a local winery

A wonderful day visiting the medioeval village of San Gimignano one of the main villages of Tuscany called the medioeval Manhatten because for all his...

6 hours Hotel pickup offered Free Cancellation

from
$999

Customised shore excursion from the port of Livorno exploring the Carrara marble quarries, the sculpture town of Pietrasanta and a Colli di Luni Vermentino wine …More

Livorno Private Shore Excursion to Pietrasanta and the Carrara Marble Quarries

Customised shore excursion from the port of Livorno exploring the Carrara marble quarries, the sculpture town of Pietrasanta and a Colli di Luni Vermentino wine...

9 hours Free Cancellation

from
$976

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

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

Siena and Chianti Country with 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 Country with 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
$689

Siena included 2Wineries & Lunch in Chianti Country 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 included 2Wineries & Lunch in Chianti Country 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
$689

Montalcino 2 Top Wineries full day Limousine Service Florence

On this Tours there is a selection of the Top Wineries of Montalcino, you will have a real Brunello di Montalcino Top experience, and a …More

Florence, Italy

Montalcino 2 Top Wineries full day Limousine Service Florence

On this Tours there is a selection of the Top Wineries of Montalcino, you will have a real Brunello di Montalcino Top experience, and a...

10 hours Hotel pickup offered Free Cancellation

from
$1,358

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

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

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

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

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 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?

Tuscany Wine Tasting & Winery Tours with Instant Confirmation include:

View all Tours with 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?

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

View all Tours with Hotel Pickup →

Got any more Tuscany trip ideas?

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