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 →

Art and Wine in the Heart of Chianti discover with us the tradition

Live an authentic experience in the heart of Chianti, unique because it combines art and wine in one path. You will not just be spectators: …More

Florence, Italy

5.0 (1)

Art and Wine in the Heart of Chianti discover with us the tradition

Live an authentic experience in the heart of Chianti, unique because it combines art and wine in one path. You will not just be spectators:...

4 hours Free Cancellation

5.0 (1)

from
$171

Taste of Tuscany San Gimignano Winery with Transfer from Florence

TOUR HIGHLIGHTS • Sample at least eleven spectacular wines, a selection of local cheeses and traditional foods and recipes of Tuscany • Benefit from a …More

Florence, Italy

4.0 (2)

Taste of Tuscany San Gimignano Winery with Transfer from Florence

TOUR HIGHLIGHTS • Sample at least eleven spectacular wines, a selection of local cheeses and traditional foods and recipes of Tuscany • Benefit from a...

4 hours Free Cancellation

4.0 (2)

from
$216

Wine Tasting & Lunch in Florence city centre

Daily, in an typical and traditional wine bar enoteca located in the heart of Florence a special event is going on: a Wine Tasting & …More

Florence, Italy

3.7 (3)

Wine Tasting & Lunch in Florence city centre

Daily, in an typical and traditional wine bar enoteca located in the heart of Florence a special event is going on: a Wine Tasting &...

1 hour 30 minutes Free Cancellation

3.7 (3)

from
$73

Our business stands out for offering a unique experience that combines equestrian adventure with the sophistication of wine tasting. We are committed to taking travelers …More

Siena, Italy

4.0 (2)

Wine and Horses

Our business stands out for offering a unique experience that combines equestrian adventure with the sophistication of wine tasting. We are committed to taking travelers...

1 day Free Cancellation

4.0 (2)

from
$339

Cooking Class and Tuscan tradition in Montepulciano

With the help of our Chef, native to this area, you will discover the unique flavors of local cuisine as you explore our traditional lifestyle. …More

Montepulciano, Italy

4.0 (2)

Cooking Class and Tuscan tradition in Montepulciano

With the help of our Chef, native to this area, you will discover the unique flavors of local cuisine as you explore our traditional lifestyle....

5 hours Free Cancellation

4.0 (2)

from
$124

Private Montalcino and Pienza Tour from Siena

Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as …More

Siena, Italy

4.0 (3)

Private Montalcino and Pienza Tour from Siena

Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as...

6 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$324

Discover Florence’s curious yet charming Oltrarno neighborhood on a sunset stroll with a guide. Set on the lesser-visited side of the River Arno, the historic …More

Florence, Italy

3.5 (2)

Sunset Stroll in Florence

Discover Florence’s curious yet charming Oltrarno neighborhood on a sunset stroll with a guide. Set on the lesser-visited side of the River Arno, the historic...

2 hours

3.5 (2)

from
$79

Private Tour Tastes of Tuscany: Pisa, Siena and Chianti

Visit the best known Tuscan cities and attractions Pisa, Chianti Classico, Siena! This private tour will be custom made according to your requirements and it can …More

Florence, Italy

3.7 (3)

Private Tour Tastes of Tuscany: Pisa, Siena and Chianti

Visit the best known Tuscan cities and attractions Pisa, Chianti Classico, Siena! This private tour will be custom made according to your requirements and it can...

10 hours Free Cancellation

3.7 (3)

from
$166

Private Chianti Wine Tour from Florence - Half-Day Experience

Go on a guided wine tasting tour around the Heart of Tuscany called Chianti. Relax and clear your mind as you taste the variety of …More

Florence, Italy

3.7 (3)

Private Chianti Wine Tour from Florence - Half-Day Experience

Go on a guided wine tasting tour around the Heart of Tuscany called Chianti. Relax and clear your mind as you taste the variety of...

6 hours Hotel pickup offered Free Cancellation

3.7 (3)

from
$227

Livorno Port ShorExcursion: Siena San Gimignano Lunch&WineTasting

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

Livorno, Italy

4.0 (1)

Livorno Port ShorExcursion: Siena San Gimignano Lunch&WineTasting

Enjoy this unforgettable Shore Excursion and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: •...

9 hours

4.0 (1)

from
$333

Half day experience for Lunch and Wine tasting around S.Gimignano

• Experience for your private group. This special tour will take you to the heart of Tuscany. Meet the real people who live and work …More

Florence, Italy

3.0 (3)

Half day experience for Lunch and Wine tasting around S.Gimignano

• Experience for your private group. This special tour will take you to the heart of Tuscany. Meet the real people who live and work...

2 hours Hotel pickup offered Free Cancellation

3.0 (3)

from
$568

Livorno Shore Excursion: Exclusive Wine Experience

You can decide whether you'd like to spend more time at the winery and just visit San Gimignano, then stop in Pisa. Alternatively, you can …More

Livorno, Italy

3.0 (1)

Livorno Shore Excursion: Exclusive Wine Experience

You can decide whether you'd like to spend more time at the winery and just visit San Gimignano, then stop in Pisa. Alternatively, you can...

5 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$324

In the heart of a 1300s village, you will discover the history and a family where the Nobile di Montepulciano will be the protagonist. Enjoy …More

Montepulciano, Italy

2.0 (1)

Montepulciano: Wine Tour and tasting

In the heart of a 1300s village, you will discover the history and a family where the Nobile di Montepulciano will be the protagonist. Enjoy...

1 hour Free Cancellation

2.0 (1)

from
$59

Private Wine Tasting & Tuscan Light Lunch - Food and Drinks included

A break of pleasure! Try your typical Tuscan products prepared by our cook with Tasting of Wines and Olive oils together the staff of Bottega …More

Poggibonsi, Italy

3.0 (1)

Private Wine Tasting & Tuscan Light Lunch - Food and Drinks included

A break of pleasure! Try your typical Tuscan products prepared by our cook with Tasting of Wines and Olive oils together the staff of Bottega...

2 hours Free Cancellation

3.0 (1)

from
$51

Truffle Hunting in the Tuscany Hills of Florence

Unleash your inner truffle hunter in Tuscany! Journey from Florence to a historic estate, greeted by stunning scenery. Meet your expert guide and their talented …More

Florence, Italy

3.0 (1)

Truffle Hunting in the Tuscany Hills of Florence

Unleash your inner truffle hunter in Tuscany! Journey from Florence to a historic estate, greeted by stunning scenery. Meet your expert guide and their talented...

5 hours Free Cancellation

3.0 (1)

from
$406

Florence's Culinary Delights A Foodie Walk Tour

Embark on a culinary adventure through the heart of Florence’s local flavor in the less-trodden district of Sant’Ambrogio. Visit the local market and treat yourself …More

Florence, Italy

3.0 (1)

Florence's Culinary Delights A Foodie Walk Tour

Embark on a culinary adventure through the heart of Florence’s local flavor in the less-trodden district of Sant’Ambrogio. Visit the local market and treat yourself...

180 to 210 minutes Free Cancellation

3.0 (1)

from
$113

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

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

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

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?

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?