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 →

Tuscan Cooking Class - Traditional 5 course menù

Kitchen has always been the fulcrum of this home, where my family is living since more than 7 generations. I have always been fascinated by …More

Montepulciano, Italy

5.0 (120)

Tuscan Cooking Class - Traditional 5 course menù

Kitchen has always been the fulcrum of this home, where my family is living since more than 7 generations. I have always been fascinated by...

5 hours Free Cancellation

5.0 (120)

from
$304

From Florence: Classic Chianti Villages and Wine Roads by Minivan

You will get the unique opportunity to taste wines and and other specialties that you will taste such as 5 white sauvignon and rosé wines …More

Florence, Italy

4.9 (80)

From Florence: Classic Chianti Villages and Wine Roads by Minivan

You will get the unique opportunity to taste wines and and other specialties that you will taste such as 5 white sauvignon and rosé wines...

6 hours 30 minutes Free Cancellation

4.9 (80)

from
$158

Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

This day trip is to explore the flavors of the land just south of Florence with its traditions for great wine, olive oil, cheese & …More

Florence, Italy

5.0 (321)

Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

This day trip is to explore the flavors of the land just south of Florence with its traditions for great wine, olive oil, cheese &...

7 hours

5.0 (321)

from
$312

Florence River Cruise on a Traditional Barchetto

Cruise along the Arno River and under the incredible Ponte Vecchio, Florence’s famous bridge, on a barchetto, a small traditional boat! Florence’s answer to the …More

Florence, Italy

4.4 (393)

Florence River Cruise on a Traditional Barchetto

Cruise along the Arno River and under the incredible Ponte Vecchio, Florence’s famous bridge, on a barchetto, a small traditional boat! Florence’s answer to the...

1 hour Free Cancellation

4.4 (393)

from
$67

Private Cinque Terre Experience from Florence

Explore the scenic Italian Riviera! Discover one of Italy’s most amazing destinations, the unforgettable Ligurian Coast of Cinque Terre, UNESCO World Heritage site. Enjoy scenic …More

Florence, Italy

4.9 (102)

Private Cinque Terre Experience from Florence

Explore the scenic Italian Riviera! Discover one of Italy’s most amazing destinations, the unforgettable Ligurian Coast of Cinque Terre, UNESCO World Heritage site. Enjoy scenic...

12 hours Hotel pickup offered Free Cancellation

4.9 (102)

from
$657

Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

Enjoy a day away from Florence as you visit Siena, San Gimignano and the picture-postcard Chianti area. Take your time to appreciate everything Tuscany has …More

Florence, Italy

4.9 (143)

Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

Enjoy a day away from Florence as you visit Siena, San Gimignano and the picture-postcard Chianti area. Take your time to appreciate everything Tuscany has...

8 hours Hotel pickup offered Free Cancellation

4.9 (143)

from
$120

Livorno: Florence Optional Walking Tour and Accademia Entry

If you are stopping for the day at the port of Livorno and want to visit Florence, this round-trip transfer makes the logistics a snap. …More

Livorno, Italy

4.3 (327)

Livorno: Florence Optional Walking Tour and Accademia Entry

If you are stopping for the day at the port of Livorno and want to visit Florence, this round-trip transfer makes the logistics a snap....

8 hours Free Cancellation

4.3 (327)

from
$40

PRIVATE Tuscan Pasta Class in Florence at Chef Cinzia's Home

For a truly memorable meal and culinary experience in Florence, join a local chef in preparing an authentic Italian menu of fresh pasta and other …More

Florence, Italy

5.0 (57)

PRIVATE Tuscan Pasta Class in Florence at Chef Cinzia's Home

For a truly memorable meal and culinary experience in Florence, join a local chef in preparing an authentic Italian menu of fresh pasta and other...

3 hours Free Cancellation

5.0 (57)

from
$169

Tuscan Cooking Class -Traditional Pasta Menu

Kitchen has always been the fulcrum of this home, where my family is living since more than 7 generations. I have always been fascinated by …More

Montepulciano, Italy

5.0 (119)

Tuscan Cooking Class -Traditional Pasta Menu

Kitchen has always been the fulcrum of this home, where my family is living since more than 7 generations. I have always been fascinated by...

4 hours Free Cancellation

5.0 (119)

from
$200

Bolgheri: Premium Wine Tasting with Winery Tour

Visit "Terre del Marchesato" vineyards, winery and wine-tasting for a 90 minutes experience tour. Nestled 3mi (5 km) from the village center of Bolgheri, you're …More

Livorno, Italy

4.9 (53)

Bolgheri: Premium Wine Tasting with Winery Tour

Visit "Terre del Marchesato" vineyards, winery and wine-tasting for a 90 minutes experience tour. Nestled 3mi (5 km) from the village center of Bolgheri, you're...

1 hour 15 minutes Free Cancellation

4.9 (53)

from
$50

Medieval Tour in Monteriggioni and Val d'Orcia from Florence

Our first stop is Pienza, a charming Renaissance village located in the heart of the Val d'Orcia. Famous worldwide for its delicious Pecorino di Pienza, …More

Florence, Italy

4.8 (70)

Medieval Tour in Monteriggioni and Val d'Orcia from Florence

Our first stop is Pienza, a charming Renaissance village located in the heart of the Val d'Orcia. Famous worldwide for its delicious Pecorino di Pienza,...

11 hours Free Cancellation

4.8 (70)

from
$49

Small Group Chianti Wine Tasting with Seven Tuscan Wines

Departs at 10am from central Florence by comfortable, air-conditioned van transport, accompanied by a bi-lingual guide. After the cantina visit, sit down and relax to …More

Florence, Italy

4.9 (104)

Small Group Chianti Wine Tasting with Seven Tuscan Wines

Departs at 10am from central Florence by comfortable, air-conditioned van transport, accompanied by a bi-lingual guide. After the cantina visit, sit down and relax to...

4 hours 30 minutes Free Cancellation

4.9 (104)

from
$143

Wine and food tasting in an organic family winery

Guided tour of our winery estate near San Gimignano: vegetable garden, orchard, vineyard, olive grove, Vin Santo aging room (vinsantaia), historic cellar, and a collection …More

San Gimignano, Italy

5.0 (153)

Wine and food tasting in an organic family winery

Guided tour of our winery estate near San Gimignano: vegetable garden, orchard, vineyard, olive grove, Vin Santo aging room (vinsantaia), historic cellar, and a collection...

2 hours 45 minutes Free Cancellation

5.0 (153)

from
$92

Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour

When your cruise ship docks in Livorno and you have only a single day to see the Tuscan countryside, you’ll need a privately guided, fully …More

Chianti, Italy

5.0 (91)

Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour

When your cruise ship docks in Livorno and you have only a single day to see the Tuscan countryside, you’ll need a privately guided, fully...

9 hours Free Cancellation

5.0 (91)

from
$206

Private Chianti Safari: Off Road Tuscany Wine Tour with Lunch from Florence

For connoisseurs and amateurs alike, there’s no better way to explore the famous Chianti vineyards and sample the world-class tipples for which the area is …More

Florence, Italy

5.0 (31)

Private Chianti Safari: Off Road Tuscany Wine Tour with Lunch from Florence

For connoisseurs and amateurs alike, there’s no better way to explore the famous Chianti vineyards and sample the world-class tipples for which the area is...

8 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$559

Small-Group Chianti Trip with Wine Tasting from Siena

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian …More

Siena, Italy

5.0 (83)

Small-Group Chianti Trip with Wine Tasting from Siena

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian...

8 hours Free Cancellation

5.0 (83)

from
$217

Located between Florence, Siena and San Gimignano, Casa Sola is a family owned boutique winery, ideal stop for those who want to discover the magic …More

Florence, Italy

4.9 (125)

Discover Chianti Through its Wines

Located between Florence, Siena and San Gimignano, Casa Sola is a family owned boutique winery, ideal stop for those who want to discover the magic...

1 hour 30 minutes Free Cancellation

4.9 (125)

from
$48

Florence: Flambé Cheese Wheel Truffle Pasta Class & Tiramisù

Enter the flambé scene with the parmesan wheel! Learn to make fresh pasta like our grandmothers made it in Italy, all done by hand. The …More

Florence, Italy

5.0 (170)

Florence: Flambé Cheese Wheel Truffle Pasta Class & Tiramisù

Enter the flambé scene with the parmesan wheel! Learn to make fresh pasta like our grandmothers made it in Italy, all done by hand. The...

3 hours Free Cancellation

5.0 (170)

from
$113

Hidden Castles & Chianti Wine Experience– Small Group

Visit two charming family-run wineries in the heart of the Chianti region, learn about local winemaking traditions, and taste 7 exquisite wines paired with bruschetta, …More

Siena, Italy

4.6 (159)

Hidden Castles & Chianti Wine Experience– Small Group

Visit two charming family-run wineries in the heart of the Chianti region, learn about local winemaking traditions, and taste 7 exquisite wines paired with bruschetta,...

5 hours Free Cancellation

4.6 (159)

from
$56

Private Brunello Wine Safari and Val d'Orcia Tour from Florence

Hop aboard our rugged offroad vehicle and experience Tuscany like never before, surrounded by cypress-lined hills, vineyards, and medieval towns. Your adventure kicks off in …More

Florence, Italy

5.0 (79)

Private Brunello Wine Safari and Val d'Orcia Tour from Florence

Hop aboard our rugged offroad vehicle and experience Tuscany like never before, surrounded by cypress-lined hills, vineyards, and medieval towns. Your adventure kicks off in...

11 hours Hotel pickup offered Free Cancellation

5.0 (79)

from
$658

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?