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The Best Chianti Wine Tours for fantastic wine tastings!

Every one of these Chianti wine tours will be full of new experiences and knowledge that will surely make a wine lover out of anyone

Table of Contents

Top 3 Wine Tasting Tours

Wine bottles - 350×265

Windering - Chianti Half-Day Wine Tour in the afternoon

One off
  • Hands-on
  • 5.5 hours
  • N/A
Top choice
Wine bottles - 350×265 (3)

Destination Florence - Chianti Half Day Wine Tour

One off
  • Hands-on
  • 5 hours
  • Max 8 ppl.
Wine bottles - 350×265 (2)

Tuscany Now and More - Horseback Riding Tour & Wine Tasting

One off
  • Hands-on
  • 2 hours
  • Max 4 ppl.

Table of Contents

Wine tours offer a delightful and immersive experience for both enthusiasts and novices alike, while providing a unique opportunity to explore the world of winemaking while indulging in the flavors of the vineyard so be sure to come and join any one of these Chianti wine tours to enjoy it for yourself.

These wine tasting tours will take the participants on a journey through picturesque vineyards, charming cellars, and, of course, tastings of exquisite wines such as the wonderful Chianti Classico. Every one of these Chianti wine tours will be full of new experiences and knowledge that will surely make a wine lover out of anyone that attends if they weren’t already one before.

Whether you are a seasoned wine connoisseur or a casual enthusiast, every one of these wine tours promises an enriching and enjoyable journey through the world of Chianti wine in the Chianti countryside!

1. Windering - Chianti Half-Day Wine Tour in the afternoon

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Join this experience and get the chance to admire the rolling hills of Chianti and taste world-class wines paired with products from the area with this afternoon wine tour.

You will visit the cellars of two of the most renowned Chianti wineries and taste their top wines which will be accompanied by delicious products from local farms such as cheese and cold cuts. You will be overwhelmed by the unique atmosphere that this corner of Tuscany offers and end your day with a walk to the Castellina in Chianti, breathe the air of the village, and explore its typical shops.

This is the perfect experience to enjoy alongside a group of friends or family members so be sure to bring them along!

2. Destination Florence - Chianti Half Day Wine Tour

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Discover the beauties and flavors of the Chianti region with this amazing wine tasting tour and you will definitely not be disappointed!

You will savor the pleasure of a real wine experience with tastings of three typical prestigious wines as well as visit the tiny village of Greve in Chianti, the so-called “capital” of Chianti. You will also enjoy a traditional meal with Tuscan specialties at the end of this experience.

This is one Chianti wine tasting that you should not miss so be sure to join and you will be talking about this experience for many years to come!

3. Tuscany Now and More - Vineyard Horseback Riding Tour & Wine Tasting in Tuscany

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Whether you are an experienced rider or simply a beginner, this wine tasting tour is for you so make sure that you do not miss your chance to be a part of it!

The tour will begin at the Monte Chiaro estate, where you will enjoy a one-hour wine tasting of four of the estate’s organic Chianti Colli Senesi wines.  Following your tasting, you will join Melissa Cipriani and her team as will begin your vineyard trail tour.

This is a truly unique experience and will surely show you a new side to Chianti wine so be sure to book your spot!

4. Chianti Wine Tour - Wine Tasting Experience in Tuscany

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This wine tasting will give you a proper introduction to the Chianti wine region with different wine tastings so be sure to book your spot!

You will visit two wineries with a guided tour of the wine cellars, vineyards and farm with a spectacular introduction to the wine traditions of Tuscany along with a guided wine tasting of course. You won’t taste world-famous gelato as a sweet treat during this experience.

You will end the day with a local lunch and you will surely be coming back many more times to enjoy everything all over again.

5. Fun in Tuscany - Chianti Wine Tour

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This is one of the Chianti wine tours that should not be missed so buckle up and join the ride as you taste amazing wine and experience something fantastic!

You will enjoy a wine tasting that includes three wines produced by the winemaker at the first winery, paired with fresh local bread, green olives, pecorino cheese, extra-virgin olive oil and balsamic vinegar as well as a lunch that will have a guided wine tasting at the second winery.

At the end of everything you will stop by Piazzale Michelangelo which has been nominated as one of the top ten most romantic spots in Europe, and get the chance to enjoy the beautiful panoramic view of the city.

6. Tuscany Tour Time - Tuscan wine tour: 3 Chianti wineries

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This wine tour will give you the chance to discover excellent Chianti wines together with great scenery, scrumptious Tuscan food, and to get the most out of these Chianti wine tastings.

At first Chianti winery, you will meet the owner or his assistant and be taken on a visit to their wine cellars. You will also taste at least 3 different wines including White wine, Chianti, Super Tuscan wine, and even extra virgin olive oil which will be accompanied with some local food. You will enjoy lunch at the second winery along with great Tuscan food, which will of course be paired with organic Chianti wine tasting

At the third Chianti winery you will experience the famous Chianti and Super Tuscan wines along with some extra virgin olive oil.

7. Under The Tuscan Sun Tours - Chianti Wine Tour Half Day

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Come and join this experience to get the chance to visit a first-class winery and taste the best selection of Tuscan wines that Chianti has to offer.

You will start your wine tour with a drive through the breathtaking Tuscan countryside as you delve into the heart of the Chianti Classico region. Over the course of the tour, you will visit a first-class winery that will give you a pairing food, wine tour and a generous tasting of the best selection of Tuscan wines on offer.

You will learn all about wines and of course taste them so be sure to bring along a few friends and to enjoy the day tour!

8. Grape Tours - Super Chianti Wine Tour: Escape Florence and spend the day in the vineyards

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Come and join this experience as it takes you from Florence into the super picturesque and delicious Chianti & Chianti Classico regions.

You will kick off the day at an old Tuscan farmhouse winery and learn about the grape-to-bottle process after which you will sit down to taste 4 beautiful wines accompanied by fresh olive oil and sheep’s milk cheeses made at the winery’s dairy farm. You will enjoy a delicious lunch featuring four meat dishes and a taste of the famous Bistecca alla Fiorentina.

You will continue on to another winery where you will be treated to a private tour and learn about the traditions of the oldest wine region of the world!

9. Florencetown - Fully immersive wine and olive oil experience in Chianti

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This wine tour will show you a fabulous side to Chianti wine so be sure that you do not miss it and bring along some friends to enjoy this experience with you.

You will be led by your sommelier and visit two very different wineries. You will experience the thrill of exploring cellars lined with precious blends, and as a bonus, both wineries are internationally renowned and acclaimed! You will learn about wine production in general and about the two different approaches and techniques, all while savoring the very best of the estate blends.

You will enjoy a typical Tuscan lunch at the end of this experience which will ensure that you walk away with a smile and a full stomach!

10. Avventure Bellissime - Private Chianti Half-Day Trip from Florence

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This is the perfect experience to be a part of and get the chance to enjoy an insider’s view of the Chianti region on this half day Chianti wine tour from Florence.

You will visit a celebrated vineyard of Chianti where you will tour the facilities of the vineyard and gain a thorough understanding of the local wine making process. You will then enjoy a full wine-tasting of at least four different wines after which you will visit a charming hill town where you will enjoy a short walk to further indulge in the beauty and local charm of this celebrated wine region.

You will pause at Greve in Chianti where you will go on a short tour of the town and you can take another optional wine tasting in an old wine cellar in the center of town.

Each one of these Chianti wine tours will be a chance for you to discover new flavors, expand your knowledge on wine, and create lasting memories surrounded by the beauty of vineyards and the artistry of winemaking.

Be sure to also take a look at these wine tours in Sicily for even more chances to take part in more fantastic wine tastings and they will surely be the highlight of your trip every time that you attend!

Disclaimer: Note that the food images displayed on this website are for illustrative purposes only. They are not indicative of the actual dishes or presentations you should expect during the classes. We strive to provide the best culinary experience, but the appearance of dishes may vary. Always refer to class descriptions and details for accurate information on what to expect.

Frequent Asked Questions

This region of Chianti sits between the beautiful cities of Florence and Siena, and the stunning hills in the region are famous all around the world for its panoramas and wines. Even though is not as big an area as some other popular regions in Italy, Chianti offers many things to see, such as medieval cities and villages, castles and parish churches.

Shoulder Seasons, April & May, except Easter, mid-September through October, is the time of year when the weather in Tuscany is the most comfortable and, except for Easter time, things will be a little less busy than usual. In spring, you may encounter a few showers but that’s what makes the wildflowers bloom.

Depending on where you where you would like to go in Chianti, you will have several itinerary options. A simple one is to start from Florence, head towards Siena and visit wineries and villages along that route, and the distance between Florence and the closest Chianti village, Greve, is about 20 miles.

For a short trip to Chianti, 2-3 days should be enough time for you to explore the main attractions and of course indulge in some wine tasting. You will be able to visit the famous wineries, local villages, as well as dine at authentic Italian restaurants.

Chianti Classico is a dry, red wine and it only gets made in a specific part of Tuscany in central Italy.

Depending on the blend of varietals, such as whether the Chianti wine is organic or not, production methods, aging, and so on, the costs will differ a lot. A Chianti Classico may cost more than a Chianti, and a Chianti Classico Riserva will probably cost the most but Chianti does have a reputation in the United States as being a cheap table wine.

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