Top Tuscany Wine Tasting Tours - page 6

The Tuscan hill town of Montepulciano is surrounded by rolling vineyards where some of Italy's most prestigious wines are produced. Delve into the world of Vino Nobile di Montepulciano with this wine tour that stops at two boutique wineries to meet the vintners and learn about the history and production of their storied reds. Stroll through the estates to take in the views, visit the cellars, and relax over a guided wine tasting.

(12)

from $33

Vino Nobile di Montepulciano Wine Tour - Meet the producers

Vino Nobile di Montepulciano Wine Tour - Meet the producers

3 hours 30 minutesFree Cancellation

4.5

(15)

from $189

A few steps from San Gimignano, there is a splendid family-run winery. Here you can taste the typical Tuscan products: starting from the wine up to tasty local croutons. You will visit the cellar, the vineyards, and all the places where the wine comes to life. You will listen to stories, and curiosities, and you will learn the winemaking processes that make Tuscany and Chianti areas to be protected and loved. You will discover the secrets of wine and grapes and the best combinations with strictly typical foods. Do not miss the opportunity to combine Tuscan wine with appetizing foods (such as cheese and ham) and find out how wines are produced in a real cellar. You can have a lovely tasting of 4 wines accompanied by snacks of typical products preceded by a tour of cellars and vines.

San Gimignano: Chianti wine tasting

1 hourFree Cancellation

4.6

(10)

from $35

Safari in Chianti Open Top Van and Tasting Wine

Soak up the Tuscan sun, and delve into Chianti's cuisine, without the hassle of navigating on this open-top minivan tour. Enjoy a scenic drive through the countryside, stopping for a tour and tasting at a local cellar. Take a stroll through the villages of Montefioralle and Greve in Chianti before sitting down to a Tuscan lunch at a second cellar featuring a multi-course meal with wine pairing.

Safari in Chianti Open Top Van and Tasting Wine

7 to 8 hoursFree Cancellation

(91)

from $235

Indulge your senses and leave planning travel logistics to someone else on a half-day tasting tour of the famous Chianti wine region. Let someone else transport you through the rolling olive groves and vineyards of the Tuscan countryside, stopping at a winery to sample the local bounty. Learn about traditional and organic wine-making methods on cellar and estate tours, and taste olive oil, cheese, and different wines, including the famous red Chianti.

Likely to Sell Out

Chianti Half-day Wine Tour in the Tuscan's Hills from Pisa

Chianti Half-day Wine Tour in the Tuscan's Hills from Pisa

4 to 5 hoursFree Cancellation

(134)

from $105

Montalcino: Brunello Wine Tasting Experience

The only authentic aperitif in the vineyard of Tuscany. It is a story of passion, of farmers, and historical places: a winery off the beaten path, far away from the crowd, but close to the Tuscan traditions. I will pick you up at your in Lucca with my professional van, and I will drive you through the hills of Tuscany. We will start our tour with a walk in the vineyard and we will visit the cellar where you will discover all the secrets of Tuscan wine, thanks to the explanations and the life stories of the farmer. Then, you will taste the wines of the production enjoying a real Tuscan atmosphere. Every wine will be matched with a few products from the garden and some specialties, like salami and pecorino cheese from Tuscany.. a dip in the Tuscan table culture! Remember: it's not a complete lunch... it is about learn how to pair wine and food :) "It's not just drinking wine: we want to make you know the real Tuscany, we want to tell you the story of our roots"

4.4

(62)

from $38

Tasting in a Tuscan Vineyard with transfer from Pisa

Tasting in a Tuscan Vineyard with transfer from Pisa

4 hoursFree Cancellation

When you’re in the Tuscan city of Siena, don’t miss the chance to discover its famous wines and enjoy some local food, too. This small-group wine tour visits a winery near Siena’s historical center, and gives the lowdown on the winery’s organic production methods. After visiting the vineyard, you’ll savor a meal made with local produce along with samples of five organic wine varietals. Numbers are limited to 12 per group.

(44)

from $105

Guided Winery Tour and Wine Tasting in Siena

2 hours 30 minutesFree Cancellation

Private Wine & Oil Tasting with Lunch

(75)

from $88

The Chianti countryside is among the most picturesque in Italy, but the lack of public transportation and confusing rural roads make exploring on your own a hassle. With this private day trip, leave the driving to a professional so you can focus on the postcard-perfect views. Enjoy hotel pickup in Florence and set the itinerary and pace you prefer, stopping to explore hill towns, visit wineries, and snap photos of the views.

4.6

(118)

from $80

Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

8 hoursFree Cancellation

(32)

from $466

Montepulciano: Wine Tasting & Lunch in a typical winery

Private Tour: Chianti Winery, Montefioralle, and Greve in Chianti

4.1

(43)

from $65

4.5

(26)

from $313

Brunello and Montepulciano Wine Tour from Cortona

6 to 8 hoursFree Cancellation

4.6

(25)

from $589

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 Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti’s rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

Chianti Half Day Wine Tasting Tour from Siena

Chianti Half Day Wine Tasting Tour from Siena

Discover Tuscany's most iconic hilltop gems on this full-day excursion from Florence. Organizing a trip to the region’s scattered medieval villages can be challenging without local insight or a grasp of the Italian language. This group experience covers the logistics, so you can spend your time basking in the beauty of Val d'Orcia, sipping wine at a rural vineyard, and exploring medieval fortresses along the way.

4.5

(11)

from $58

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

11 hoursFree Cancellation

4.8

(30)

from $183

Trade the busy streets of Florence for the ancient vineyards, medieval villages, and scenic landscapes of the Chianti wine region on this half-day tour. Let a knowledgeable local driver take you to some of the area’s best family-run wineries, where you can learn about traditional production methods and taste the local bounty like extra-virgin olive oil and renowned wine varietals like Chianti Classico. The private tour can be customized to suit your interests, such as a stop for an authentic Tuscan lunch at a local farm.

Half Day Chianti Wine Tour with Private Luxury Van

Private Tuscany Horse Ride, Wine Tasting and local food at Estate

(22)

from $696

Per group

5 hours 30 minutesFree Cancellation

(54)

from $377

Rent an electric bicycle in Montepulciano and visit the wineries of Tuscany without getting too tired. Thanks to the extra sprint it gives you over hilly terrain, the electric bike is the perfect way to explore the country lanes and soak up the landscape of the famous wine region. Following a planned route, you will be able to visit a selection of local wineries and enjoy two wine tastings in their cellars.

Wine Tour Ebike Experience

Spend a day cycling through the beautiful Tuscan hillsides surrounding Florence on an easy-to-pedal e-bike. Travel through the enchanting landscape of vineyards, villas, and olive orchards, stopping to take photos. Learn more about the area’s history from your friendly guide, and avoid the risk of getting lost. Stop at a family-run Chianti wine estate for a guided tour and a traditional homemade Tuscan lunch, with wine and olive oil tastings.

(180)

from $188

E-bike Chianti Classico Tuscany Tour with Wine and Lunch at Farm

E-bike Chianti Classico Tuscany Tour with Wine and Lunch at Farm

7 hoursFree Cancellation

Florence: Flambé Cheese Wheel Truffle Pasta Class & Tiramisù

(46)

from $188

3 hoursFree Cancellation

Riding a Vespa is a quintessential Italian experience and, with this small-group tour, you don’t need a motorbike license to enjoy it. Simply join an intimate gathering of like-minded folk, meet your personal driver, don your helmet, and hop aboard. See Florence’s UNESCO World Heritage–listed center up close and enjoy stunning city views from Piazzale Michelangelo, the village of Fiesole, and a hilltop church.

(199)

from $116

Small-Group Florence Vespa Passenger Ride with Wine Window

Small-Group Florence Vespa Passenger Ride with Wine Window

Experience medieval Tuscany on a group day trip. Visit the fortified town of Monteriggioni with tickets to its Templar Museum and access to its medieval walls. Continue on to the UNESCO heritage area of Val d'Orcia and stop at the medieval village of Montalcino for an optional taste of local wine and nibbles. Finish your tour with a wander through Pienza before the scenic drive back to Florence.

(36)

from $140

Medieval Tour in Monteriggioni and Val d'Orcia from Florence

Medieval Tour in Monteriggioni and Val d'Orcia from Florence

11 hoursFree Cancellation

4.8

(73)

from $51

Swap your typical night out for something different with this interactive bar crawl across Florence. Combine bar visits with a walking tour of the city's key historic landmarks. With your guide in the lead, spot Medici–era landmarks, visit the Santa Croce district, and soak up the city's centuries of history. In between, enjoy a range of drinks, from traditional cocktails to digestivi served through the city's unique "wine windows."

Tipsy Tour: Guided Bar Crawl In Florence with Dark History

3 hoursFree Cancellation

(335)

from $77

Experience Tuscany's wine culture on this private wineries tour. Ideal for travelers based in Florence, explore beyond the city without having to hire a car. Travel with a knowledgeable sommelier guide through rolling hills and vineyards, visiting three estates to sample regional wines and olive oil. Enjoy a traditional Tuscan lunch at a family-owned winery paired with wine. Perfect for food lovers looking to immerse themselves in local flavors.

Exclusive Private Tuscany Wine Tour & Food Pairing Session

Exclusive Private Tuscany Wine Tour & Food Pairing Session

8 hoursFree Cancellation

(72)

from $590

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines

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What are people saying about Tuscany

Emily_U, Aug 2026

Beautiful day in Val d’Orcia

This was a great day trip from Florence. Our guide Carmella was great and so knowledgeable about the history of the region and the towns we were visiting. It felt like the perfect amount of time in each place too. Montepulciano was almost empty in the morning as our first stop and the wine tasting there was great, even with it being 10am! We had a great lunch in Pienza at the next stop and took in the beautiful views. Montalcino was the final stop and felt like a town out of a storybook.

Florence Accademia Gallery Tour with Entrance Ticket Included

LindaA_M, Aug 2026

Skip the line David.

The meeting point was easy to find. Our tour guide, Martina met us, gave us our hearing devices and led us easily through the entrance. Skip the line tour is the only way to go. The line was long and moved very slowly. Martina was excellent. She was extremely knowledgeable about the painting and artist. Martina told us about Michelangelo’s early life leading up to his famous sculptures and paintings. David was spectacular and Martina pointed out details that most of us would not see. This tour was well worth the price. Marina was an excellent tour guide.

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

Nicole_G, Jul 2026

Wonderful experience!

We had a wonderful experience learning about the wines at Tenuta Adamo. Our guide was very knowledgeable and the wine was delicious. If you are not familiar with the area it is okay to drive over the bridge, we were confused at first but once you drive up to the winery there was plenty of space to park.

Pastamania 1st Pasta Class in Florence with Museum

Rebecca_S, Jul 2026

A really special way to spend an afternoon.

A really lovely experience. Elouise was a wonderful guide to all things pasta and along with giving a clear lesson, with lots of individual attention and guidance, she was really knowledgeable about the cultural and historical importance of communal making and sharing of food. We all really enjoyed the afternoon, and the food, and felt able to take the skills and knowledge back to our own kitchen, to share with the rest of the family.

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Amy_I, Jul 2026

Great day trip in Tuscany

We loved our day on this tour! Valentina was an amazing guide and gave us so much information about the area before we arrived at the first winery. Views were amazing and we loved the differences in visiting both a small and larger winery. And both had amazing wine! Our time in San Gimignano was short (90 min) but gave us enough time to do some shopping, grab some gelato and enjoy the views. We had 8 people on our trip but it didn’t feel crowded, and we enjoyed getting to know the other travelers. Highly recommend this tour!

Half-Day Chianti Wine Tasting from Florence with Two Wineries

Daria_B, Jul 2026

We had a great time, the...

We had a great time, the winery representatives were knowledgeable and friendly. The view of Tuscan countryside was fantastic. The bus was comfortable (I’d suggest playing some Italian music to enhance the experience though). The tasting experience was nice, we tasted a variety of products, but I’d add some more cheese/salami to complement the wine. Overall, I recommend this tour.

Siena, San Gimignano and Chianti Wines Day Tour from Florence

Diana_M, Jul 2026

Roberto and Leon were...

Roberto and Leon were amazing tour guides.we loved the trip. It was so organized and clear from the beginning to the end. It was just enough for all that we saw. Unbelievable landscapes and the preparation of Roberto was excellent. Mario is the best bus driver I've ever had. He's an expert at driving and carefulness.

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.

Wine Experience In Chianti Hills from Florence

Leah_W, Jun 2026

Great experience meeting point not clear

The Wine tasting was lovely however the meeting point was not clear at all - it’s tucked away. Other tours I’ve been on the meeting point was at the bus parking lot (where our guide actually led us to) and that was actually easier to find than meeting in the station. I would suggest someone waiting out of the ticked away place with a clear flag as it was a stressful start to the trip and also meant as a couple we couldn’t sit together on the bus.

Cinque Terre Full Day Tour with Optional Pisa Stop from Florence

Tony_R, May 2026

This was by far the best...

This was by far the best day we’ve had in Italy so far!! Alex was our tour guide and he definitely made the trip more fun!! He is super knowledgeable and all instructions were very clear on where to go and when! Post card views of all of the different towns! The views are absolutely AMAZING!

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.