This is a guest post by Melissa Younger of Crowdsourced Explorer
Tuscany is one of the best places in Italy for wine tasting. It is full of vineyards, wineries, wine shops, restaurants, and even old castles that offer tantalising wine tastings. Some are simple and intimate experiences, while others are designed for connoisseurs. Here are our recommendations for wine tasting in Tuscany.
Local Recommendations For Wine Tasting In Tuscany
One local on Crowdsourced Explorer shared their experience of wine in the Montepulciano area, saying that the red wine grape of the region is “grown widely in central Italy, most notably its eastern Abruzzo, Marche and Molise regions. The variety was named after the Tuscan parish of Montepulciano, but, confusingly, is not used in the famous wines produced there. Montepulciano produces a Rosso di Montepulciano, a Vino Nobile di Montepulciano, and a Vin Santo di Montepulciano”.

Another local shared this information about Siena: a “tiny but beautiful medieval city, surrounded by nice hills in Tuscany. While visiting the area you can enjoy wonderful wine and good food. Nature is at its best here and landscapes are awesome”.
Tuscany is famous for its wines, unmatched in quality and variety. You’ll want to sample some of the best local wines such as Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano. Take a look at some of the best places to sample wines in this famous wine-producing region.
Arezzo
Santa Vittoria Winery
At the Santa Vittoria Winery in Arezzo, you’ll get the chance to see how wine has been made over the years, dating back to the 18th century. The guides are knowledgeable and will give you a tour, followed by a tasting. They pair wine with fresh food made from the farm or with traditional crafted Italian dishes.
You will be immersed in the history and culture of Tuscany as you sample their unique and elegant wines. Be sure to book your spot ahead of time!
Siena
Castiglion Del Bosco Winery
The winery of Castiglion del Bosco in Siena overlooks a beautiful vineyard and park. You can enjoy wine tasting surrounded by scenic hills, forests, and mountain ridges.
Here, you’ll find wines made from Sangiovese grapes, including three kinds of Brunello and a Rosso di Montalcino. You can also taste wines made at Prima Pietra, their other vineyard, which produces Merlot, Cabernet Sauvignon, Cabernet Franc and Petit Verdot.
Their signature wine tour includes a trip to the cellars, where you will see how the wine is made, and tasting of six of their best wines, paired with Tuscan cheese, bread, olive oil, and honey.
Their wine and cheese pairing provides you with a tasting of their six best wines, including the exclusive Vin Santo and cheeses such as aged Tuscan Pecorino. The Brunello Vertical Tasting is a private tasting of six of their finest Brunello di Montalcino wines alongside some Pecorino cheese, bread, house made extra virgin olive oil, and honey. You can make a reservation in advance.

Fattoria Di Montemaggio
There are many unique wine tasting experiences at the Fattoria do Montemaggio. First, there’s their Total Immersion Wine Tour with Blind Tasting, which takes you through the vineyards, gardens, cellar and tasting room. The tasting includes sampling all the wines, having some snacks, then a blind tasting using black glasses so you cannot see the wine. This tour lasts 2½ hours.
Their Full Immersion Wine Tour with Mini Tasting Course is the same tour but with a tasting of 8 of their wines, served with local cheeses, cured meats, bread, and house-made extra virgin olive oil. The tour and tasting take 2 hours. The Classic Wine Tour, lasting 1 hour and 15 minutes, is similar but with five different wines.
Their Mini Wine Tour is a shorter tour with a tasting of three wines and house-made olive oil. It lasts for 40 minutes. You should book your tour and tasting in advance if possible.
LivItaly have a whole range of small group tours throughout Italy. Readers of this site can get a 5% discount on all of their tours by using discount code BEWITCHEDBYITALY
Tenuta Casanova
At the Tenuta Casanova winery, you’ll sample exclusive wines that are not available in shops or restaurants. Owners Rita and Silvano offer a unique wine tasting with scented wines such as Easy to Fall in Love, a Champagne they make with Chardonnay and Malvasia, and Magnificat – The Pope Wine – a rare wine from 1850 with only 300 bottles.
Their Wine Tasting Tour takes one hour and also showcases their aged balsamic vinegar and extra virgin olive oil.

Florence
Luciano Winery
At the Luciano Winery, there are several different tours and tastings. Enjoy the atmosphere of the villa and cellar from the Middle Ages as you learn about the history and taste some elegant wines. Each wine tasting includes a tour and sampling three or four wines. paired with food. You can enjoy a Private Tasting in a climatised room, a Basic Tasting, or seasonal tastings.
There is also a Mystery Tasting, which includes a tour and a guided tasting with a sommelier, who will challenge you to answer questions about three different wines, including a mystery one. You can book a tour and tasting in advance.
Fattoria Viticcio
At the Fattoria Viticcio winery, there are many ways to enjoy tasting their wines and food. You can start with A Taste of Tuscany in their tasting room, which is a 20-30 minute guided wine tasting. It does not require a reservation. Their Chianti Classico Wine & Food Experience takes an hour and a half and includes a visit to the winery, a cellar tour, and a guided tasting of three wines paired with their olive oil, bread, and charcuterie.
For an immersive experience, you can take their Private Wine Masterclass with professional winemaker Daniele Innocenti. You’ll taste, identify, and blend up to four kinds of grapes as you learn their characteristics. You can enjoy a traditional Tuscan lunch with your wine and will get to take three bottles away with you! The tour, class, and lunch take 2 hours.
You’ll need to make a reservation for the wine and food experience or the masterclass.

Castello Del Trebbio
For a medieval experience, you’ll want to look at the wine tasting options at Castello del Trebbio. Their Cellar Tour lasts an hour and a half and teaches you about the castle’s history and their wines. You will get to taste three of their wines.
The two-hour Royal Tour guides you through their history and wine, including a tasting of four wines paired with their Biointegrali® products. The two-hour Vertical Lastricato Tasting is ideal for connoisseurs. You will taste versions of their Lastricato Chianti Rufina Riserva, surrounded by coats of arms and led by a specialist. To book a tour and tasting, visit the website.
Enoteca Pitti Gola E Cantina
The Enoteca Pitti Gola e Cantina is a restaurant offering a long list of high-end, rare Italian wines from all over Italy. Their wine tastings inform you about the history, production and characteristics of Italian wine as you enjoy their delicious fare.
Their Wine Tasting Lunch allows you to sample four wines during three courses crafted by Chef Matteo Caironi. You will order from their seasonal Classic or Vegetarian menu, and the staff will help you pair wines with your dishes. During their Wine Tasting Dinner, you will similarly choose four wines to accompany your three courses.
The Flights allows you to taste four glasses of wine. There are three themed options for this tasting: Discover Italy, Forty Years of Chianti, and The Bubbles Flight. It is highly recommended that you reserve a place in advance.
Fiesole
Poggio La Noce
The Poggio La Noce wine estate offers an authentic wine tasting experience in the countryside. Sit among the rolling hills of Fiesole as you sample their wines made from some of the best grapes in Italy. From the eldest Sangiovese vines, planted in 2000, the estate produces the top wine Gigiò. The additional vines were planted a few years later with slightly different soil characteristics and different blends
They blended Sangiovese, Colorino and Canaiolo grapes to produce red wines called Gigetto and Gigino and a rosé, Pinko Pallino. Their white wine, Bàja, is a 100% Falanghina that has been aged in steel.
Owners Claire and Enzo do not use chemicals, and the estate is 100% organic. Their tasting is personal and intimate, and includes a tour of their vineyard and winery. Contact the wine estate to book a tasting.
Want to learn more about what there is to do in Tuscany? See what locals are sharing on Crowdsourced Explorer.