Top Tuscany Wine Tasting Tours

Small-Group Wine Tasting Experience in the Tuscan Countryside

4 hours 45 minutesFree Cancellation

Venture into Tuscany on this day trip from Florence and discover the region's highlights with the help of a local guide. Explore the medieval city of Siena and its cathedral before heading to the hills of Chianti for a Tuscan lunch and wine tasting (optional). Roam the streets of San Gimignano and travel to Pisa to admire the architectural drama of Cathedral Square—home to the UNESCO-listed Leaning Tower of Pisa. Upgrade to include admission to climb the tower.

(8,097)

from $104

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

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

12 hoursFree Cancellation

(23,170)

from $111

Get a taste of Tuscany's culinary legacy on this wine and food tour from Florence. Led by a guide, travel through the Tuscan hills in a 4WD vehicle, stopping to visit historic wine estates and cellars along the way. Sample specialities at each stop, and enjoy a 3-course meal in the Tuscan countryside before returning to Florence. With several touring options available, find one that'll suit your schedule and budget.

SMALL-GROUP Wine Safaris: Tuscany Wine Tasting Tour from Florence

7 to 9 hoursFree Cancellation

Sample Italy's flagship Brunello di Montalcino wine in the hills where it’s produced with this exclusive winery tour and tasting at a medieval castle. Join a sommelier for a stroll through the vineyards to learn about the history and production of Brunello at this family-run estate, then relax over a tasting that pairs three different wines with local specialties. Cap off your experience with a three-course Tuscan lunch.

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

1 hour 30 minutesFree Cancellation

4.7

(117)

from $69

Likely to Sell Out

Montepulciano: Winery Tour & Tasting Experience

Enjoy 1.5 hours wine tasting experience in an historical cellar in the heart of Montepulciano. Together with an expert sommelier, discover the cellar’s underground of XVI century characterized by vaults and tunnels attributed of Etruscan civilization. Listen the history of this ancient cellar as well as the explanation of the methods and techniques of the wine production. During this journey follows a unique tradition in high quality wine production. Furthermore, discover private collection of old wine bottles tunnel and be amazed by the Etruscan tomb located in the cellar. Then, take part to an exclusive wine tasting experience combined to regional products. A sample of four local wines will be served with bread with a plate of local products. During this experience, you will taste four of the most important wines made in Montepulciano and known all around the world while a professional sommelier will explain you in depth the particularity of those Italian excellencies.

Montepulciano: Winery Tour & Tasting Experience

1 hour 20 minutesFree Cancellation

4.6

(135)

from $41

Half day Chianti Vineyard Escape from Florence with Wine Tastings

5 hoursFree Cancellation

The Tuscan region of Chianti is known for its wine, but sussing out the best wineries on your own can take hours of research. Skip the hassle and head straight to three hand-picked wineries to tour the wine cellars and taste different varietals on this group wine tour from Florence. Midday, treat your senses to a light lunch of fresh regional products like bruschetta, handmade pasta, cheese, and salami. You'll also travel through the Tuscan countryside dotted with vineyards, olive groves, and villas, stopping to explore the traditional village of Greve.

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

8 hoursFree Cancellation

Tasting Tour in One of The Most Beautiful Cellars in the World

(1,440)

from $174

1 hourFree Cancellation

4.8

(290)

from $38

Spend a day in the beautiful Tuscan countryside sipping wine and making new friends. Visit authentic wineries for tours and generous tastings of world-famous varietals like Chianti Classico and Super Tuscan. Learn about wine production and flavor profiles, and round out your palate with samplings of high-quality balsamic vinegar and olive and truffle oils. Also, visit the charming medieval village of San Gimignano for free time to explore the winding streets and artisan shops.

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

7 hoursFree Cancellation

Learn the secret to preparing pasta from scratch like a true Italian “nonna” in the heart of Florence with this hands-on pasta cooking class. Make three types of fresh pasta plus traditional sauces with guidance from your instructor as you sip unlimited Tuscan wine and connect with fellow foodies. Then cap off your lesson by sampling your creations with a celebratory meal served with even more wine.

(1,128)

from $105

Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

2 hours 30 minutesFree Cancellation

Experience the true flavor of the Tuscan countryside and go wine tasting without having to drive on this Chianti wine tour from Florence. Led by a professional tour escort, visit local wineries in scenic villages to sample revered Tuscan wines and learn winemaking secrets. Alternatively, enhance your day with a morning cooking class preparing traditional Tuscan recipes paired with premium wines.

(8,336)

from $29

Half-Day Chianti Wine Tasting from Florence with Two Wineries

5 hours 30 minutesFree Cancellation

4.5

(4,339)

from $64

Montepulciano: Cinta Senese Farm Tour, Food Tasting & wine

2 hoursFree Cancellation

4.8

(21)

from $69

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Embark on a delightful day trip through Tuscany's iconic Val d'Orcia, a UNESCO World Heritage Site. Visit Montalcino, home of Brunello wine, Pienza, famed for Pecorino cheese, and Montepulciano, celebrated for Nobile wine. Enjoy breathtaking views, rich culture, and mouthwatering food. Travel in comfort aboard a premium minivan with an English-speaking driver. Indulge in wine tastings, a superior lunch with a view (seasonal), and guided vineyard and cellar tours.

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

10 hours 30 minutesFree Cancellation

4.7

(392)

from $267

Price varies by group size

A Brunello Cooking Class with Vineyards View Winery

Cooking Class in a Tuscan Castle Brunello Winery

4 hoursFree Cancellation

Chianti is home to the scenic wine country and notable cellars, but getting there on unfamiliar rural roads on your own can be challenging. This group wine tour takes you to two different wineries in the Tuscan hills to explore the vineyards and their cellars, as well as relax over guided tastings. Sip local reds and whites, plus sample balsamic vinegar and extra-virgin olive oil, while enjoying views over the Chianti countryside.

From Florence: Chianti Wine Experience with Tastings & Views

5 hours 30 minutesFree Cancellation

4.4

(837)

from $41

Bolgheri: Classic Wine Tasting with Winery Tour

1 hour 15 minutesFree Cancellation

4.7

(333)

from $29

Strike out from Lucca to explore the vineyard-covered hills without having to navigate the confusing country roads with this wine tour that includes pickup and all-day transportation. Stop for tours and tastings in two boutique cellars to meet the winemakers and sample their wines, served with local pecorino cheese, cold cuts, and other delicacies. Learn about the traditional techniques and modern innovations behind some of Tuscany’s top wines.

Tuscan Wine Tour in Lucca by van

5 to 6 hoursFree Cancellation

(206)

from $174

Avoid the hassle of planning routes between scattered wine towns and booking separate tastings on your own with a guided day trip from Siena. This experience connects the flavors of Montepulciano and Pienza with the scenic landscapes of Val d'Orcia, letting you move easily between villages without logistics stress. Spend your time enjoying wine, local food, and countryside views at a relaxed pace.

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

10 to 11 hoursFree Cancellation

Combine medieval history, regional wine, and UNESCO-listed monuments on this full-day tour from Florence. This is an ideal choice for anyone who wants to experience wine tasting without getting behind the wheel afterwards. Visit Monteriggioni's medieval castle, explore Siena's historic architecture, and admire San Gimignano's skyline. End with a tasting of three Chianti wines and an opportunity to savor authentic, local flavors.

Siena, San Gimignano and Chianti Wines Day Tour from Florence

10 hours 30 minutesFree Cancellation

4.6

(3,081)

from $76

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

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

9 hoursFree Cancellation

Take a break from sightseeing and head to the hills surrounding Lucca to sample the area’s excellent wines. Connect with a winemaker at a boutique winery for a relaxed private tour through the vineyards and cellar, with plenty of time to ask questions about the history and production of the local vintages. Then relax on the terrace overlooking the rolling countryside to sample the estate’s wines and olive oil while enjoying the view.

(1,004)

from $221

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

1 hour 30 minutesFree Cancellation

4.8

(434)

from $23

Wine and food tasting in an organic family winery

San Gimignano is surrounded by quiet countryside dotted with small wine estates. Visit one of these traditional farms and connect with local hosts on this tour and wine tasting experience. Take in the organic farm's garden, orchard, vineyard, olive grove, "vinsantaia" aging room, and cellar. Then enjoy a tasting of eight organic wines of your choice paired with the farm's own olive oil plus local cheeses and cold cuts and other culinary combinations.

Wine and food tasting in an organic family winery

2 hours 45 minutesFree Cancellation

Siena: A Wine Tour and Tasting Experience

(176)

from $93

3 hoursFree Cancellation

Montalcino: Brunello Wine Tasting Experience

(387)

from $99

1 hour 30 minutesFree Cancellation

4.4

(61)

from $38

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Top Attractions in Tuscany

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What are people saying about Tuscany

Half-Day Chianti Wine Tasting from Florence with Two Wineries

Renid_D, Jul 2026

Awesome experience!

The wineries we visited had some lovely people working there and were family owned. The tour operators were also kind and helpful and took their time to give a brief history lesson of Chianti region and the wineries. You also get to meet new interesting people! Overall very fun experience and would go again!

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

Emily_B, Jul 2026

What a fun day spent in...

What a fun day spent in the Tuscan countryside. Our driver Leo was very knowledgeable and entertaining. We really enjoyed being introduced to some of the delicious wines of the Chianti area. After driving i. A rental car for most of our trip to Italy, it was nice to be able to sit back and relax. Full day but our whole family (sons 19 and 22).

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

nora_m, Jun 2026

So much more than a wine-tasting!

More than a corporate wine tour, this felt like a home visit with friends. Alice was a warm and wonderful guide who explained the history of the castle, the origins of winemaking in the region, and daily life in her part of Tuscany. A wonderful, unexpected afternoon. And of course, the wine was top-notch.

Siena, San Gimignano and Chianti Wines Day Tour from Florence

Nisha_G, Jun 2026

The tour was great, only...

The tour was great, only thing was that it felt like 3 hours was a bit too long in Siena summer heat, especially if opting for the self guided tour, and the time in Monteriggioni felt a bit too short. Otherwise, the tour was awesome and the guides were great, professional, and helpful.

Chianti Vespa Tour with Tuscan Lunch or Dinner from Florence

Elizabeth_P, Jun 2026

Great guide, even better flexibility

Tomas was a great guide and had amazing energy. I appreciate that we had a Vespa driving test before we took it out on the roads. Both my husband and I struggled and we were able to switch to driving a topolino instead for no extra cost. I’m grateful for the flexibility! The lunch and wine tasting afterward was short but a fun time.

Tasting Tour in One of The Most Beautiful Cellars in the World

Cosmin_C, Jun 2026

spectacular underground "Cathedral of Wine" experience

Our tasting tour at De'Ricci Cantine Storiche was nothing short of magical! It is easy to see why this is considered one of the most beautiful cellars in the world. The architecture and atmosphere alone are breathtaking, but the experience was made truly extraordinary by our guide, Emilio. Emilio was amazing—incredibly engaging, knowledgeable, and passionate. He took the time to explain the history of the cellars and the nuances of each wine, making the entire tasting both educational and fun. He didn't just lead a tour; he provided us with a world-class experience. If you are a wine lover or just appreciate incredible history and beauty, this tour is an absolute must. Highly recommended!

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Elizabeth_H, Jun 2026

One of my favorite...

One of my favorite experiences in Tuscany! It's also a great hot weather activity. It was 95F the day I did the tour, but the van had great AC. The first vineyard has a fantastic view -- you're outside, but in the shade and it's earlier in the day. The second vineyard is inside with great AC. All the hosts were welcoming, helpful, and generous with the wine. Couldn't recommend more (esp as a solo traveler).

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

Michele_C, Jun 2026

Overall, it is a...

Overall, it is a well-organized, jam-packed tour. We did feel a little rushed to be back on time to move on to the next town. We usually like these tours to get an overview and then return at our own leisure to explore further. If you are expecting more than 1.5 hrs to explore each area, I would keep searching or limit your tour to only 2 towns. Siena was our favorite.

Half day Chianti Vineyard Escape from Florence with Wine Tastings

Samantha_P, Jun 2026

BEAUTIFUL scenery and...

BEAUTIFUL scenery and delicious wine! As someone who has never done a wine tasting, there was wonderful variety and the vineyards felt like a fairytale. Bus ride was about an hour but there were snacks provided with the tasting and the opportunity to purchase wine. They also gave 20 minutes at each vineyard for taking pictures and exploring

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

Rosina_G, May 2026

Beautiful Winery!

Had a great experience at this winery. They offered pick-up transportation which made everything really easy, and the driver was super friendly! The winery grounds and views overlooking the Tuscan hills were so beautiful. Our guide was very knowledgeable, and the wines were excellent, smooth and perfectly paired with fresh bread and olive oil. Definitely recommend if you’re visiting Tuscany for a day trip!

Montepulciano: Winery Tour & Tasting Experience

Margaret_D, Nov 2025

Private Tour: Highly Recommend

We happened to be the only family on the morning tour, so we enjoyed a private tour with our sommelier, Luigi. He provided a wealth of insight into the wine making process, effects of soil and climate, as well as regional differences that impact taste and quality. We tasted four wines with local bread, cheese, salami, and pancetta during which Luigi answered our many questions with good humor. The newly renovated tasting room in the deep Etruscan cellars was captivating and added to the experience. We enjoyed the Talosa Reserve and Rossi IGT Pietrose so much we shipped several home. A terrific experience; we highly recommend.