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 →

PRIVATE Florence Market Tour & Cooking Class in Mirella's Home

This will be a fun filled culinary experience of buying food, talking about food, preparing food and finally eating together with a local culinary expert …More

Florence, Italy

5.0 (12)

PRIVATE Florence Market Tour & Cooking Class in Mirella's Home

This will be a fun filled culinary experience of buying food, talking about food, preparing food and finally eating together with a local culinary expert...

4 hours Free Cancellation

5.0 (12)

from
$329

Brunello di Montalcino, small biodynamic wineries

The Brunello Organic and Biodynamic Wine Tour is a full day (8/9 hours) trip to Montalcino including a visit with tastings and Tuscan lunch to …More

Florence, Italy

5.0 (12)

Brunello di Montalcino, small biodynamic wineries

The Brunello Organic and Biodynamic Wine Tour is a full day (8/9 hours) trip to Montalcino including a visit with tastings and Tuscan lunch to...

8 hours Free Cancellation

5.0 (12)

from
$262

Food and Wine Lesson and Wine Tasting in San Gimignano

The tasting of the six wines and their combinations will be presented and served in our equipped and comfortable tasting room, where all our guests, …More

San Gimignano, Italy

5.0 (11)

Food and Wine Lesson and Wine Tasting in San Gimignano

The tasting of the six wines and their combinations will be presented and served in our equipped and comfortable tasting room, where all our guests,...

1 hour 30 minutes Free Cancellation

5.0 (11)

from
$74

Private Chianti Countryside Vespa Tour from Florence

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

5.0 (11)

Private Chianti Countryside Vespa Tour from Florence

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

5.0 (11)

from
$456

Enjoy a 3-hour tour through the wonderful Tuscan hills and old historical farm houses, hamlets, and castles to explore Brunello wine country. Tutored wine tasting …More

Chianti, Italy

5.0 (11)

Brunello Vineyards Bus Tour

Enjoy a 3-hour tour through the wonderful Tuscan hills and old historical farm houses, hamlets, and castles to explore Brunello wine country. Tutored wine tasting...

3 hours

5.0 (11)

from
$184

Discover the Chianti Classico wines from an eTuk, from which you can enjoy the a drive through the vineyard covered hills around Siena to a …More

Siena, Italy

5.0 (11)

Wine Tuk Tour Siena

Discover the Chianti Classico wines from an eTuk, from which you can enjoy the a drive through the vineyard covered hills around Siena to a...

3 hours

5.0 (11)

from
$149

Wine Tour in the Countryside of Lucca with Lunch - with Minivan

This tour is including a car at your disposal during the tour, transfer to a beautiful winery in Montecarlo where you can taste 4 different …More

Lucca, Italy

5.0 (11)

Wine Tour in the Countryside of Lucca with Lunch - with Minivan

This tour is including a car at your disposal during the tour, transfer to a beautiful winery in Montecarlo where you can taste 4 different...

5 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$195

Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

Private tour to San Gimignano and Chianti with an English speaking driver in a deluxe minivan. Your driver will delight you with live commentary on …More

Florence, Italy

5.0 (11)

Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

Private tour to San Gimignano and Chianti with an English speaking driver in a deluxe minivan. Your driver will delight you with live commentary on...

8 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$129

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally …More

Siena, Italy

4.9 (11)

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally...

4 hours Free Cancellation

4.9 (11)

from
$249

Pisa, Vinci, Tuscany, Wine tasting all in one day! - Small Group

If you only have one free day in Florence and you wish to tick some of the must-dos off your bucket list, this is the …More

Florence, Italy

5.0 (11)

Pisa, Vinci, Tuscany, Wine tasting all in one day! - Small Group

If you only have one free day in Florence and you wish to tick some of the must-dos off your bucket list, this is the...

8 hours Free Cancellation

5.0 (11)

from
$216

In the heart of the Bolgheri DOC, Le Vigne di Silvia is a family-run winery dedicated to the production of high quality wines, capable of …More

Livorno, Italy

5.0 (11)

Wines and flavors of Bolgheri territory

In the heart of the Bolgheri DOC, Le Vigne di Silvia is a family-run winery dedicated to the production of high quality wines, capable of...

1 hour 30 minutes Free Cancellation

5.0 (11)

from
$68

Montecarlo E-Bike One Day Tour with Lunch and Tasting

An e-bike tour through the picturesque medieval village of Monte Carlo di Lucca in Tuscany, is a journey through time, exploring its cobbled streets and …More

Lucca, Italy

5.0 (10)

Montecarlo E-Bike One Day Tour with Lunch and Tasting

An e-bike tour through the picturesque medieval village of Monte Carlo di Lucca in Tuscany, is a journey through time, exploring its cobbled streets and...

5 to 6 hours Free Cancellation

5.0 (10)

from
$183

Montepulciano Wine Tasting in the Tuscan Countryside

An intimate and relaxing experience that begins with a tour of the winery and the cellar, followed by a tasting of 3 wines from our …More

Montepulciano, Italy

4.9 (10)

Montepulciano Wine Tasting in the Tuscan Countryside

An intimate and relaxing experience that begins with a tour of the winery and the cellar, followed by a tasting of 3 wines from our...

45 minutes Free Cancellation

4.9 (10)

from
$28

From Livorno Port: Private Volterra, San Gimignano & Wine Lunch

Spend a day through the Chianti sweet hills. A wonderful Experience between art, wine and local food to discover vineyards, towers and typical farms. • …More

Livorno, Italy

5.0 (10)

From Livorno Port: Private Volterra, San Gimignano & Wine Lunch

Spend a day through the Chianti sweet hills. A wonderful Experience between art, wine and local food to discover vineyards, towers and typical farms. •...

8 hours Free Cancellation

5.0 (10)

from
$188

Private Tour: Medieval Val d'Orcia by Minivan from Florence

Leaving from Florence, this 9-hours tour by air-conditioned minivan will let you dive into the breathtaking and delicate Val d'Orcia. In this valley you will …More

Florence, Italy

4.9 (10)

Private Tour: Medieval Val d'Orcia by Minivan from Florence

Leaving from Florence, this 9-hours tour by air-conditioned minivan will let you dive into the breathtaking and delicate Val d'Orcia. In this valley you will...

9 hours Hotel pickup offered Free Cancellation

4.9 (10)

from
$165

Brunello Wine Tour Experience Small Group Only

Perfect for wine aficionados and nature lovers alike, the Brunello Grand Tour Experience offers a deep dive into the world of one of Italy’s most …More

Florence, Italy

5.0 (10)

Brunello Wine Tour Experience Small Group Only

Perfect for wine aficionados and nature lovers alike, the Brunello Grand Tour Experience offers a deep dive into the world of one of Italy’s most...

9 hours Free Cancellation

5.0 (10)

from
$330

Chianti Half Day Wine Tasting Tour from Siena

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in …More

Siena, Italy

4.8 (10)

Chianti Half Day Wine Tasting Tour from Siena

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in...

5 hours Free Cancellation

4.8 (10)

from
$56

PRIVATE Florence Market Tour & Pasta Class in Cinzia’s Home

Meet your host Cinzia, a kind and gentle host for whom food is love and life, and explore her favorite local food stores to shop …More

Florence, Italy

5.0 (10)

PRIVATE Florence Market Tour & Pasta Class in Cinzia’s Home

Meet your host Cinzia, a kind and gentle host for whom food is love and life, and explore her favorite local food stores to shop...

4 hours Free Cancellation

5.0 (10)

from
$189

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan …More

Siena, Italy

5.0 (10)

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan...

8 hours Hotel pickup offered

5.0 (10)

from
$227

Pisa and Florence Private Tour with Wine Tasting

Discover the Essence of Tuscany: Pisa, Florence & Chianti Wine Experience Immerse yourself in the timeless beauty of Pisa and Florence—two of Tuscany’s most iconic …More

Livorno, Italy

4.9 (10)

Pisa and Florence Private Tour with Wine Tasting

Discover the Essence of Tuscany: Pisa, Florence & Chianti Wine Experience Immerse yourself in the timeless beauty of Pisa and Florence—two of Tuscany’s most iconic...

9 hours

4.9 (10)

from
$1,255

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?