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 Wine and Vinci half day Small Group Tour from Montecatini Terme

Experience a relaxed afternoon in the Chianti area with a special visit to a boutique winery. Enjoy our guided Chianti Wine tasting and a visit …More

Montecatini Terme, Italy

5.0 (34)

Chianti Wine and Vinci half day Small Group Tour from Montecatini Terme

Experience a relaxed afternoon in the Chianti area with a special visit to a boutique winery. Enjoy our guided Chianti Wine tasting and a visit...

4 hours 30 minutes Free Cancellation

5.0 (34)

from
$136

4 Wines & 2 Olive Oils Tasting in Chianti Winery with Tour

The experience will start with the winery tour, during which we will explain our company history and what we produce today and we will explain …More

Florence, Italy

4.8 (21)

4 Wines & 2 Olive Oils Tasting in Chianti Winery with Tour

The experience will start with the winery tour, during which we will explain our company history and what we produce today and we will explain...

1 hour 30 minutes

4.8 (21)

from
$41

Wine tasting in the historical Cantalici winery

The tasting at Cantalici is a way to immerse yourself in a familiar atmosphere to discover typical wines from the Chianti Classico production area, an …More

Lucca, Italy

4.8 (31)

Wine tasting in the historical Cantalici winery

The tasting at Cantalici is a way to immerse yourself in a familiar atmosphere to discover typical wines from the Chianti Classico production area, an...

50 minutes

4.8 (31)

from
$17

Private Wine and Extra Virgin Olive Oil Tasting

Escape to a charming family farm and immerse yourself in the authentic flavors of Tuscany. Just a short walk from San Gimignano’s historic center, this …More

San Gimignano, Italy

4.8 (21)

Private Wine and Extra Virgin Olive Oil Tasting

Escape to a charming family farm and immerse yourself in the authentic flavors of Tuscany. Just a short walk from San Gimignano’s historic center, this...

45 minutes Free Cancellation

4.8 (21)

from
$48

Small-Group Vernaccia di San Gimignano Wine Tour - White and Red Wines

This tour takes you to visit two wine region of Tuscany famous for red and white wines. We will make a stop at San Gimignano …More

Florence, Italy

4.8 (22)

Small-Group Vernaccia di San Gimignano Wine Tour - White and Red Wines

This tour takes you to visit two wine region of Tuscany famous for red and white wines. We will make a stop at San Gimignano...

7 hours

4.8 (22)

from
$325

1-Hour Guided Tuscan Wine Tasting in Florence

All wines for the experience are exclusive in Florence and not exported outside Italy; very small production wineries, organic, biodynamic, or natural. A pure, genuine, …More

Florence, Italy

5.0 (6)

1-Hour Guided Tuscan Wine Tasting in Florence

All wines for the experience are exclusive in Florence and not exported outside Italy; very small production wineries, organic, biodynamic, or natural. A pure, genuine,...

1 hour Free Cancellation

5.0 (6)

from
$80

Private 3hour Horse Ride to a Castle, Wine Tasting and local food

The guests will have the chance to escape from the city crowd and experience the authentic Florence life style held on the worldwide known Chianti …More

Florence, Italy

5.0 (9)

Private 3hour Horse Ride to a Castle, Wine Tasting and local food

The guests will have the chance to escape from the city crowd and experience the authentic Florence life style held on the worldwide known Chianti...

7 hours Free Cancellation

5.0 (9)

from
$792

Tuscany Organic Wine Tour at a Family-Run Winery

Discover authentic Tuscany with a guided wine tour at Podere Pellicciano, a family-run organic winery located in the hills of San Miniato, between Florence and …More

Lucca, Italy

5.0 (22)

Tuscany Organic Wine Tour at a Family-Run Winery

Discover authentic Tuscany with a guided wine tour at Podere Pellicciano, a family-run organic winery located in the hills of San Miniato, between Florence and...

2 to 3 hours Free Cancellation

5.0 (22)

from
$80

Quad Tour ATV Adventure in Chianti. Lunch and Wine Tasting

Come and discover the wild heart of Chianti, together with us you can live an experience totally immersed in the green of the countryside and …More

Florence, Italy

5.0 (35)

Quad Tour ATV Adventure in Chianti. Lunch and Wine Tasting

Come and discover the wild heart of Chianti, together with us you can live an experience totally immersed in the green of the countryside and...

6 to 8 hours Free Cancellation

5.0 (35)

from
$367

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

Half Day Chianti Wine Tour with Private Luxury Van

• Experience for your private group. Visit some of the most famous vineyards, see their wine cellars and taste excellent wines on this 5-hour tour. …More

Florence, Italy

5.0 (20)

Half Day Chianti Wine Tour with Private Luxury Van

• Experience for your private group. Visit some of the most famous vineyards, see their wine cellars and taste excellent wines on this 5-hour tour....

5 hours Hotel pickup offered Free Cancellation

5.0 (20)

from
$677

Montecatini Terme cycle and wine tasting visit

A relaxing experience cycling on secondary roads through very flat route countryside, with a visit to the hilltop village of Montecarlo (the only short climb …More

Montecatini Terme, Italy

5.0 (24)

Montecatini Terme cycle and wine tasting visit

A relaxing experience cycling on secondary roads through very flat route countryside, with a visit to the hilltop village of Montecarlo (the only short climb...

5 hours Free Cancellation

5.0 (24)

from
$193

Hire your Local Wine Guide in Bolgheri for private tastings

We are Francesca & Margarethe, both WSET Level 3 Award recipients, living in the picturesque wine region of Bolgheri, located along the stunning Tuscan coast. …More

Livorno, Italy

5.0 (22)

Hire your Local Wine Guide in Bolgheri for private tastings

We are Francesca & Margarethe, both WSET Level 3 Award recipients, living in the picturesque wine region of Bolgheri, located along the stunning Tuscan coast....

6 hours Free Cancellation

5.0 (22)

from
$144

Small family-run winery, certified organic, which produces exclusively from its own grapes with a strong focus on sustainability. We will offer you a private tasting …More

Florence, Italy

5.0 (20)

Classic Wine Tasting by Carus Wines

Small family-run winery, certified organic, which produces exclusively from its own grapes with a strong focus on sustainability. We will offer you a private tasting...

2 hours Free Cancellation

5.0 (20)

from
$23

Private Chianti Rufina Half Day Tour with Lunch from Florence

Chianti Rufina, the smallest and highest-elevation sub-region in Chianti, is celebrated for its high-altitude vineyards that add unique tannic structure to its wines. Located northeast …More

Florence, Italy

5.0 (2)

Private Chianti Rufina Half Day Tour with Lunch from Florence

Chianti Rufina, the smallest and highest-elevation sub-region in Chianti, is celebrated for its high-altitude vineyards that add unique tannic structure to its wines. Located northeast...

7 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$435

Brunello and Montepulciano Wine Tour from Cortona

In you are in Cortona, come enjoy the “Brunello and Montepulciano Tour”.. with its picturesque villages, rolling hills and unforgettable red wines… this is a tour for …More

Arezzo, Italy

4.9 (23)

Brunello and Montepulciano Wine Tour from Cortona

In you are in Cortona, come enjoy the “Brunello and Montepulciano Tour”.. with its picturesque villages, rolling hills and unforgettable red wines… this is a tour for...

6 to 8 hours Hotel pickup offered Free Cancellation

4.9 (23)

from
$328

The Experience includes: ️ Historic Estate Tour Explore our 1810 wine cellar and the ancient olive mill, while learning about the rich history of Chianti. …More

Siena, Italy

5.0 (3)

Wine & Cheese Experience

The Experience includes: ️ Historic Estate Tour Explore our 1810 wine cellar and the ancient olive mill, while learning about the rich history of Chianti....

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$68

Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied …More

Chianti, Italy

4.9 (23)

Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied...

8 hours Hotel pickup offered Free Cancellation

4.9 (23)

from
$1,091

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 (10)

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 (10)

from
$215

Chianti & Supertuscan Private Tour 2 Wineries with light lunch

Live as a Tuscan is out way to say. Don't loose the oportunity to visit places where Tuscan are usually to spend time. If you …More

Versilia, Italy

5.0 (8)

Chianti & Supertuscan Private Tour 2 Wineries with light lunch

Live as a Tuscan is out way to say. Don't loose the oportunity to visit places where Tuscan are usually to spend time. If you...

7 hours Free Cancellation

5.0 (8)

from
$169

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?