Famous for its stunning Renaissance art and architecture, Florence is Italy’s most celebrated city. The city’s strategic location makes it an ideal starting point for a memorable road trip to Tuscany and to enjoy the world-famous Chianti wine region. As you can easily imagine, there are some fantastic Tuscany wine tours from Florence, and joining one (or more) will be among the highlights of your Italian journey.
After traveling a couple of times to Florence, I must admit that I adore Chianti wines. Touring Tuscany’s wineries and participating in local wine tastings are probably among my favorite things to do in Italy. Therefore, in this article, you will find the best wine tours from Florence and how to book them. Moreover, I’ll share the prices and durations of these wine trips and various tips. Last but not least, you’ll see some of my Tuscany photos.
So, let’s start with the best Florence wine tours and what to expect from them.
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The best Tuscany wine tours from Florence
The wine tours of Tuscany from Florence will give you an excellent opportunity to explore Italy’s most beautiful region. You will visit famous cities like Siena, which also has great wine tastings, and San Gimignano, as well as picturesque villages and valleys. That said, these tours are not just about sipping a glass or two; they are also an excellent option for further exploring Tuscany.
So simply pick one or more wine tastings and discover the sweetest side of Italy.
Florence: Chianti Wineries Tour with Food and Wine Tasting
That’s one of the best half-day wine trips you can take from Florence. In addition, it’s a great introduction to Tuscany’s beautiful landscapes. On this tour, you will visit two wineries in the Chianti Hills, where local winemakers will show you their vineyards. Of course, you’re here to taste local wines, and here’s what to expect.
The guide will pick you up from your hotel, and he will share facts about the region during the drive. After you arrive at the first winery, you’ll learn about the wines produced on-site, and you’ll see the facilities. Then, your first wine-tasting session will start, consisting of four different Chianti Classico wines. Italian snacks like bread, extra virgin olive oil, cheese, and ham will also be on the table.
After the first wine tasting, your guide will take you to the second winery. Here, you’ll learn about wine production methods and why they depend so much on the weather. Finally, you’ll taste three regional wines and enjoy some free time before returning to Florence.
Duration: 5,5 hours.
Price: from 55 euros per person.
How to book: Book here the Chianti Wineries Tour
Val D’Orcia: Cheese and Wine Tasting Tour from Florence
The fertile valley of Val D’Orcia is the undeniable pearl of Tuscany. A UNESCO World Heritage Site, Val D’Orcia is the most picturesque area in Italy. The tall cypress trees, the stunning nature, and the Chianti farms create an almost impressionistic painting. For me, no visit to Tuscany is complete without a stop in Val D’Orcia.
The Chianti Classico region always offers a marvelous wine-tasting experience, and this tour is literally on another level. While driving through the fruitful valley, you will visit the most famous wine villages of Tuscany. Specifically, you will stop at Montalcino, renowned for its Brunello wine. On a local wine estate, you’ll taste different wines before heading to Pienza.
Pienza might not ring a bell, but it’s actually the prototype of modern cities. Dubbed the “Ideal city of the Renaissance,” Pienza is a small Tuscan town full of charm. This tiny place fascinated me with its history and the Piccolomini family’s past, and I even wrote an extensive Pienza travel guide.
Afterward, you’ll visit another iconic wine estate in Montepulciano. The small Montepulciano has a rich wine tradition, and that’s where the Vino Nobile vineyards are.
Relax on the drive through the Tuscan countryside on the way to Montalcino. Try some world-renowned Brunello wine and stroll through the cellars and museum of a wine estate. You’ll enjoy a wine tasting paired with Pecorino cheese, and early in the evening, you’ll return to Florence.
Duration: 11,5 hours.
Price: 92 euros per person.
How to book: Book here the Val D’Orcia tour
Small-Group Wine Tasting Tour to Tuscany
Small group tours are ideal for people willing to interact with their guides more. This small group wine tour from Florence will take you through clusters of cypress trees and the beautiful Tuscan landscape before reaching the wineries.
The Chianti Classico wine region will unfold behind the minibus’ windows while your guide will drive you to the wine estates. The two wineries this tour visits are among the most famous in Tuscany, and you’ll taste three wines in each. Apparently, the usual platters will be on the table: salami, cheese, and Italian bruschetta.
Learning more about each winery’s history is, of course, integral to this tour. Italian winemakers are passionate about their work and will share various Chianti wine tips and secrets with you.
Duration: 4,5 hours.
Price: 89 euros per person.
How to book: Book here the small group wine-tasting
Tuscany Day Trip with Lunch at Chianti Winery
This one is hands down one of the best Tuscany wine tours from Florence. However, you must take the full-day package to truly make the most of it. As you will shortly read, the full version of this trip will take you to the most iconic places in Tuscany. On the other hand, you can reduce the time (and cost) and only join a part of it. Let’s make everything clear.
The meeting point is Florence’s central train station; from there, you’ll head to Siena. That’s Italy’s most famous medieval city, featuring the fascinating Piazza del Campo. After enjoying a walking tour in Siena, you’ll continue to San Gimignano, a stunning small city known for its medieval towers. San Gimignano is a UNESCO World Heritage Site and a Tuscan gem. Finally, you’ll reach Pisa, where you can visit the world-famous Leaning Tower while enjoying other monuments.
Now, you can choose to add the lunch option, which comes with a wine tasting, and I highly recommend doing that. Tasting four Chianti wines during the tour will make your day trip to Tuscany so much nicer. Plus, you can choose to take this day trip as a private wine tour in Tuscany!
Duration: 12 hours
Price: from 105 euros per person
How to book: Book the day trip with lunch
Chianti wine tour with tastings
That’s actually one of the most beloved Tuscany wine tours starting from Florence. Apart from being one of the most affordable wine trips in Tuscany, this tour will take you to a unique place.
Specifically, you will visit two wineries after traveling along the famous Via Chiantigiana. There, you’ll have the opportunity to learn about the region while tasting different wines accompanied by snacks. The cellars, the gardens, and the deep knowledge of local winemakers guarantee an immersive experience. And, of course, you can buy bottles of wine straight from the producers.
However, this tour is unique due to the fact that after the tour, you’ll stop at Greve. Greve is one of the most picturesque Tuscan villages, and its medieval style will fascinate you. The village is the birthplace of Giovanni da Verrazzano, the famous explorer who traveled to North America in 1524. The half-day trip allows you to explore Greve at your own pace.
In my opinion, combining super Tuscan wine tastings with exploration is one of the best things to do in Italy.
Duration: 5-6 hours
Price: 55 euros per person
How to book: Book here the Chianti wine tour with tastings
Chianti day trip on a Vespa
Italy is a synonym for Vespa, and if you feel like traveling through the Tuscan countryside on the iconic vehicle, then this day trip from Florence is for you. The beautiful farms, olive trees, and narrow roads of Tuscany will unroll in front of your eyes—let alone the rich vineyards, of course!
This tour will take you to the heart of Tuscany, where clusters of medieval villages create a fantastic atmosphere. You can choose to drive the Vespa yourself or have an expert driver do that. No matter what, this Vespa Chianti tour lasts several hours and will give you hundreds of photos from Tuscany. Of course, this half-day trip includes a wine tasting with lunch.
For me, that’s one of the best wine trips for Vespa lovers because it combines two different elements -driving and drinking- in one strike.
Duration: 6 hours.
Price: 129 euros per person.
How to book: Book here the Chianti day trip with a Vespa
Florence Wine Tasting and Tuscan Lunch in a Vintage Fiat 500
Finally, if you are more of a Fiat 500 person and you’d rather cruise Tuscany with it, this tour is definitely for you. The iconic Italian vehicle became a synonym for local style and easygoing rides. Therefore, on this Chianti day trip, you’ll have the opportunity to sit behind the wheel of the retro Italian car and drive through the region.
And how about wine? Well, it is, of course, included. The tour will take you to a 15th-century villa, where you’ll tour its vineyards. However, the best part of this wine trip is the walk in the cellar, where award-winning wines are stored. And that’s exactly the wine you’ll taste, accompanied by a platter of local delicacies.
In my opinion, that’s a fantastic experience for Fiat 500 lovers and people who prefer to enjoy the scenic ride more than their glass of wine. Remember: you’ll have to remain sober to enjoy this trip fully!
Duration: 4 hours.
Price: 165 euros.
How to book: Book here the vintage Fiat 500 tour.
Tuscany wine tour facts
Joining a Tuscan wine tour is one of the best experiences you can enjoy on this side of Italy. To fully understand the country’s most iconic region, here are five facts about Tuscany’s wines. These facts will give you a better perspective on the area and help you understand why Tuscan wines are so famous worldwide.
- Tuscany’s wine production is not split equally between red and white. In fact, more than 90% of its production is red wine.
- The grape used for Tuscany’s red wine is mainly the famous Sangiovese.
- The term Super Tuscan Wines describes red wines that include non-indigenous grapes, like Cabernet Sauvignon and Merlot.
- According to historians, Tuscan wines have been produced in the same region for more than 2,500 years. Most likely, the wine tradition of the area started in the times of the Etruscans.
- Tuscany’s world-famous wines are Chianti Classico, Brunello di Montalcino, Vin Santo, and Vino Nobile.
The best Tuscany wine tours from Florence: conclusion
Florence (Italian: Firenze), the cradle of the Renaissance, is among the most legendary European cities. Walking in its streets is like exploring a vast open-air museum where art and history are forever tied. Although there are plenty of things to do in Florence, I always recommend taking a full-day trip out of town. Big cities can often exhaust you, and since Tuscany’s countryside is just a few miles away, it’ll be a pity to miss it.
The Tuscany wine tours from Florence will give you deeper insights into the area’s viticulture and expose you to breathtaking landscapes. Any of the Florence wine trips mentioned above will take you to must-see places. Moreover, you’ll have the option to explore the Chianti region and taste world-famous wines.
Even if you have just a couple of days in Florence, taking a tour is a must: Tuscany is Italy’s most beautiful region, and seeing places like San Gimignano and Pienza is a lifetime experience.
More about Florence: Florence art tours, Facts about Florence, My Florence travelogue
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Last Updated on January 15, 2025 by George Pavlopoulos