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 →

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day …More

Florence, Italy

4.9 (24,384)

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day...

12 hours Free Cancellation

4.9 (24,384)

from
$92

Pasta & Pesto Class with a View, plus Tiramisù & opt. Market Tour

Indulge your love of Italian food in Tuscany, and enjoy a full-day tour that combines a market visit with a cooking class and 4-course meal …More

Florence, Italy

5.0 (5,141)

Pasta & Pesto Class with a View, plus Tiramisù & opt. Market Tour

Indulge your love of Italian food in Tuscany, and enjoy a full-day tour that combines a market visit with a cooking class and 4-course meal...

5 hours Free Cancellation

5.0 (5,141)

from
$45

Tuscany in One Day: Pisa, Siena, San Gimignano & Chianti Lunch

Spend the day discovering the highlights of the Tuscan countryside on this guided tour, together with its amazing art cities and tasting food & wine. …More

Florence, Italy

4.8 (2,646)

Tuscany in One Day: Pisa, Siena, San Gimignano & Chianti Lunch

Spend the day discovering the highlights of the Tuscan countryside on this guided tour, together with its amazing art cities and tasting food & wine....

12 hours Free Cancellation

4.8 (2,646)

from
$74

Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch

Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable …More

Florence, Italy

4.9 (1,877)

Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch

Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable...

10 hours Free Cancellation

4.9 (1,877)

from
$170

Florence Cooking Class: Lasagna, Tiramisu & Market or Pasta Class

Join one of the most authentic Florence Cooking Class experiences and choose between two unforgettable culinary adventures. Learn from professional local chefs in Florence's first …More

Florence, Italy

4.9 (1,842)

Florence Cooking Class: Lasagna, Tiramisu & Market or Pasta Class

Join one of the most authentic Florence Cooking Class experiences and choose between two unforgettable culinary adventures. Learn from professional local chefs in Florence's first...

5 hours Free Cancellation

4.9 (1,842)

from
$55

Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner

Discover the real essence of the Tuscan countryside, driving through amazing postcard views; departing from Florence, in a small group, that means top comfort and …More

Florence, Italy

5.0 (1,590)

Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner

Discover the real essence of the Tuscan countryside, driving through amazing postcard views; departing from Florence, in a small group, that means top comfort and...

8 hours Free Cancellation

5.0 (1,590)

from
$170

Full Day Tour to Val d'Orcia with Wine & Cheese Tastings

Enjoy a rich and ripe tour through the worlds of grape and gourmet cheese. Experience art and architecture and blend it with good wines and …More

Florence, Italy

4.8 (1,379)

Full Day Tour to Val d'Orcia with Wine & Cheese Tastings

Enjoy a rich and ripe tour through the worlds of grape and gourmet cheese. Experience art and architecture and blend it with good wines and...

11 hours 30 minutes Free Cancellation

4.8 (1,379)

from
$105

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

This is our best-selling tour that has made us famous among the public. It’s the perfect balance between cycling, admiring beautiful landscapes and tasting the …More

Florence, Italy

5.0 (1,309)

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

This is our best-selling tour that has made us famous among the public. It’s the perfect balance between cycling, admiring beautiful landscapes and tasting the...

6 hours Free Cancellation

5.0 (1,309)

from
$138

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

A day trip exploring Tuscany with visits to 2 wineries. Taste 8 different types of wine, three extra virgin olive oils, balsamic vinegar and Tuscan …More

Florence, Italy

4.9 (1,270)

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

A day trip exploring Tuscany with visits to 2 wineries. Taste 8 different types of wine, three extra virgin olive oils, balsamic vinegar and Tuscan...

7 hours Free Cancellation

4.9 (1,270)

from
$85

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover …More

Siena, Italy

4.9 (1,035)

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover...

9 hours Free Cancellation

4.9 (1,035)

from
$217

Florence Pasta Making Class or Lasagna, Tiramisu & Market Tour: choose between two hands-on Florence cooking class options with professional local chefs. This product includes …More

Florence, Italy

5.0 (1,001)

Florence Pasta Making Class or Lasagna, Tiramisu & Market Tour

Florence Pasta Making Class or Lasagna, Tiramisu & Market Tour: choose between two hands-on Florence cooking class options with professional local chefs. This product includes...

3 hours Free Cancellation

5.0 (1,001)

from
$55

Florence Evening Food Tour with Florentine Steak & Tuscan Wine

Navigating Florence’s food scene on your own can mean missing the city’s most genuine flavors. With 14 tastings at 4 local restaurants and a super …More

Florence, Italy

4.9 (838)

Florence Evening Food Tour with Florentine Steak & Tuscan Wine

Navigating Florence’s food scene on your own can mean missing the city’s most genuine flavors. With 14 tastings at 4 local restaurants and a super...

3 hours 30 minutes Free Cancellation

4.9 (838)

from
$65

Small Group Wine Tour & San Gimignano Visit

Small Group/ Two wineries/ San Gimignano/ lunch/ guided wine tastings/ gelato world champion/ piazzale Michelangelo and more.. First we tour vineyards and cellar of an organic …More

Florence, Italy

4.9 (808)

Small Group Wine Tour & San Gimignano Visit

Small Group/ Two wineries/ San Gimignano/ lunch/ guided wine tastings/ gelato world champion/ piazzale Michelangelo and more.. First we tour vineyards and cellar of an organic...

8 hours Free Cancellation

4.9 (808)

from
$217

Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

You have dreamed of a romantic Italian getaway. Be ready to make that dream a reality with this 4+ hour Fiat 500 tour from Florence …More

Florence, Italy

4.9 (664)

Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

You have dreamed of a romantic Italian getaway. Be ready to make that dream a reality with this 4+ hour Fiat 500 tour from Florence...

4 hours Free Cancellation

4.9 (664)

from
$139

Florence Exclusive PRIVATE Food Tour with 6 or 10 Tastings

Eat your way through Florence's culinary scene on a private food tour. Go on a delicious journey as you try 6 or 10 of the …More

Florence, Italy

4.8 (648)

Florence Exclusive PRIVATE Food Tour with 6 or 10 Tastings

Eat your way through Florence's culinary scene on a private food tour. Go on a delicious journey as you try 6 or 10 of the...

3 hours Free Cancellation

4.8 (648)

from
$79

Tuscan Countryside Vespa Tour from Florence with Wine

Escape from the crowded streets of the city to see life as a local as you zip around the stunning Tuscan countryside on a REAL …More

Florence, Italy

4.9 (619)

Tuscan Countryside Vespa Tour from Florence with Wine

Escape from the crowded streets of the city to see life as a local as you zip around the stunning Tuscan countryside on a REAL...

5 hours Free Cancellation

4.9 (619)

from
$194

Tuscany Vespa Tours Through the Hills of Chianti

There is nothing more exciting and unique than driving a vespa through the Tuscan hills. Live “La Dolce Vita” with us. Our Tuscany Vespa Tours …More

Florence, Italy

5.0 (575)

Tuscany Vespa Tours Through the Hills of Chianti

There is nothing more exciting and unique than driving a vespa through the Tuscan hills. Live “La Dolce Vita” with us. Our Tuscany Vespa Tours...

6 hours Free Cancellation

5.0 (575)

from
$184

Florence Pasta & Tiramisu Cooking Class with Unlimited Wine

Learn the art of authentic Italian cuisine in the heart of Florence’s historic center. Guided step by step by expert chefs, you’ll learn how to …More

Florence, Italy

4.9 (567)

Florence Pasta & Tiramisu Cooking Class with Unlimited Wine

Learn the art of authentic Italian cuisine in the heart of Florence’s historic center. Guided step by step by expert chefs, you’ll learn how to...

2 hours 30 minutes Free Cancellation

4.9 (567)

from
$34

Florence Food & Wine Tour: Tuscan Tastings in the Historic Center

Gelato, Chianti wine, olive oil, and authentic Tuscan dishes—this Florence food tour is a feast for the senses. Discover the flavors of Cucina Povera, learn …More

Florence, Italy

4.9 (546)

Florence Food & Wine Tour: Tuscan Tastings in the Historic Center

Gelato, Chianti wine, olive oil, and authentic Tuscan dishes—this Florence food tour is a feast for the senses. Discover the flavors of Cucina Povera, learn...

2 hours 30 minutes Free Cancellation

4.9 (546)

from
$97

Florence Small-Group Pasta Class Seasonal Ingredients with Wine

This is not just a cooking class — it’s a fully immersive culinary experience inside a real cooking school in Florence, where every detail is …More

Florence, Italy

5.0 (525)

Florence Small-Group Pasta Class Seasonal Ingredients with Wine

This is not just a cooking class — it’s a fully immersive culinary experience inside a real cooking school in Florence, where every detail is...

2 hours 30 minutes Free Cancellation

5.0 (525)

from
$125

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?

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?