15 Best Wine Tastings And Tours In Chianti

The wine tastings and tours in Chianti are something you should try at least once (or many times – no judgement here!) in your life. That’s because Chianti is famous for its wine, particularly the Chianti Classico, a red wine made primarily from Sangiovese grapes.

This region’s winemaking process is embedded into its cultural heritage and the traditions that have established the wineries and companies that are offering the best Chianti wine tours.

Our team has lined up 15 of their favorite wine tastings and tours in Chianti. Check out their ratings for yourself! You just have to pick the one that appeals to your preferences and level of curiosity.

Chianti Wine Tour from Florence

Region: Chianti, Tuscany, Italy

2500 five-star ratings can’t be wrong. On this Chianti wine tour from Florence, you’ll pass through the Sienese Chianti Classico region along the historical “Via Chiantigiana” and be rewarded with a family-run organic winery and stunning views of the undulating hills that have made this region of Tuscany so well-known. A passionate winemaker will greet you here and take you on a little stroll through the vines and down the slope. 

Upon arrival, you’ll be greeted with a tasting of four distinct wines and exclusive local products followed by a guided tour of the cellars and the beautiful, aromatic garden.

Why we love this tour: Can I just say first that the garden is so pretty! Also, I love that it’s very convenient and comfy because they pick you up from Florence in an air-conditioned coach.

From $49.59

Greve in Chianti Wine Tasting and Winery Tour

Region: Chianti, Tuscany, Italy

There is no better joy for a true wine enthusiast than discovering how their favorite Tuscan red wine is produced. This comprehensive wine-tasting and winery tour in Chianti is of a family-owned, organic winery. They’ll teach you everything there is to know about Chianti Classico. 

Explore the picturesque vineyard and savor four distinct red wines within the ambiance of the on-site cellar. Enjoy your tasting with some salami and fresh cheeses that are produced locally.

Why we love this tour: I personally loved the extra virgin olive oil – I took one (OK, three) home.

From $55.10

Private Wine Tours VIP: Wines and Wineries of Chianti Classico

Region: Chianti, Tuscany, Italy

Take advantage of this exclusive wine trip in a Mercedes E-Class with onboard Wi-Fi and a driver who is an expert on local wines. Discover Chianti in style straight from your Florence vacation rental/hotel. Pay-as-you-go tickets for entry, lunch, and samples while you dine at the upscale Poggio Amorelli winery and savor wines like Super Tuscans and Chianti Riserva. You can also sample extra virgin olive oil and balsamic vinegar.

Why we love this tour: Aside from the wine tour itself, you’ll stop at places that have the most breathtaking views, and you can take some photos. Make a stop at the FAMOUS Antinori nel Chianti Classico winery. It’s part of this luxurious tour!

From $837.48

Semi-Private Chianti Wine Tour, Siena Underground & San Gimignano

Region: Florence to San Gimignano

Join this small-group, private trip from Florence to San Gimignano to sample some of the most well-known white wines in Italy. All-day transportation is included while you explore a boutique vineyard, Piazza del Campo, medieval caves, and other lesser-known Siena attractions. Indulge in the region’s renowned ice cream, cheese, bruschetta, and salami, as well as Chianti wine.

Why we love this tour: Visiting lesser-known Siena attractions was one of the highlights for me on this tour. You’ll get to explore a medieval cave, the medieval square, and the beautiful Gothic cathedral in the area.

From $154.34

Chianti Wine Tour with Tuscan Lunch, Open Top Van, Max 6 Pax

Region: Chianti, Tuscany, Italy

Take an open-air minivan tour to experience famous Chianti cuisine while soaking up the Tuscan sun. Your group will drive across the countryside after leaving Florence, stopping at a local cellar for a tour and tasting. 

After taking a tour through the Chianti towns of Montefioralle and Greve, enjoy a traditional Tuscan lunch at a second cellar where each course is paired with a different wine.

Why we love this tour: We had quite a hard time booking this tour because it’s always sold out! Who doesn’t want to experience driving through Italy in an open-air minivan???? It was really cool.

From $198.35

Chianti Wine Tour: Tuscan Reds

Region: Chianti, Tuscany, Italy

The purpose of this five-red wine tasting is to give you a thorough understanding of the Chianti Rufina region. The robust character of Sangiovese grapes in a Chianti Rufina vintage will greet you at the start of your voyage, followed by the allure of Super Tuscans and Chianti Rufina Reserves.

Why we love this tour: This is a one-of-a-kind experience because the villa belongs to the most ancient Florentine family. This family has been producing wine for 25 generations!!

From $38.57

Half Day Chianti Wine Tour with Private Luxury Van

Region: Chianti, Tuscany, Italy

Enjoy a fascinating half-day exploring the historic vineyards, medieval towns, and renownedly beautiful scenery of the Chianti wine area. When you hire a private luxury car from Florence, you can have a knowledgeable local driver take you to some of the best family-run wineries in the region. There, you can sample the region’s produce, such as extra-virgin olive oil and well-known wine varietals like Chianti Classico, and learn about traditional production methods. 

You can tailor the private tour to your preferences, for example, by including a stop at a nearby farm for a traditional Tuscan lunch.

Why we love this tour: It’s very flexible because you can choose where you want to go. We definitely stopped for a traditional Tuscan lunch at a farm, and it was worth it.

From $550.98

Sunset VIP Chianti Wine Tour

Region: Chianti, Tuscany, Italy

Come along for a 4-hour tour of Tuscany’s renowned Chianti Valley, a culinary utopia for foodies. This semi-private tour will demonstrate what foodies and wine enthusiasts go from all over the world to enjoy. 

As you tour local wineries for special samples straight from their cellars and vineyards, your guide will share information on the history and enology of the area. To top it all off, there can be an optional lunch.

Why we love this tour: We had free time to explore the narrow alleys and cute boutique shops along Castellina In Chianti. That’s where I bought a souvenir!

From $247.94

Small-Group Chianti Tradition Wine Tour

Region: Chianti, Tuscany, Italy

One of the most well-known wine regions in Tuscany is only a short drive from Florence, yet the majority of Chianti’s small, independent producers are hidden away in the picturesque hills and are only well-known to locals. With this tour, you may visit family-run Chianti Classico wineries without having to drive. With the assistance of a knowledgeable wine guide, take advantage of two stops for wine tastings and a winery dinner.

Why we love this tour: Do you know that Tuscan delicacies are fantastic? I didn’t! That’s why I was very fascinated with the winery dinner. And the delicacies are paired with Chianti Classico.

From $292.02

Off-Road Wine Tour in Chianti from Florence

Region: Chianti, Tuscany, Italy

Wine and driving don’t go together, so take advantage of this guided tour and let your guide take you on an off-road adventure through the Chianti Valley. Enjoy 15 wine tastings, honey and olive oil tastings, and a traditional Tuscan picnic lunch in a vintage SUV while touring three distinct wine caves.

Why we love this tour: They were not kidding when they said ‘wine tour’ because we literally tasted 15 wines along with honey and olive tastings. The traditional Tuscan picnic lunch is the cherry on top. Just perfect.

From $444.09

Chianti Half-Day Wine Tour in the Tuscan Hills from Pisa

Region: Chianti, Tuscany, Italy

Take a half-day tasting tour from Pisa to the well-known Chianti wine area and indulge your senses. See the sloping vineyards and olive groves of the Tuscan countryside while stopping at a winery to taste the nearby produce. 

Take an olive oil tasting and sample a variety of wines, including the well-known red Chianti, while learning about organic and traditional winemaking techniques and taking cellar and estate visits.

Why we love this tour: They say it’s the Italians’ traditional way of life – after taking a tour of the vineyard, we tasted a selection of wines with typical bruschetta, pecorino chees, and ham.

From $98.07

Walking Tour of Siena with Food & Chianti Wine

Region: Chianti, Tuscany, Italy

Tour Siena with a local guide to gain insight into the city that the guidebooks are unable to provide. In a small, ten-person group, you will stroll through Siena, learning about the background of the adjacent monuments and the UNESCO-listed Piazza del Campo while also enjoying traditional Tuscan fare and Chianti wine.

Why we love this tour: Get the best vantage points in Siena with this walking tour. I might have taken millions of selfies and landscape photos because the neighborhood is just so beautiful!

From $68.05

Siena, San Gimignano, and Chianti Wine Small-Group Tour from Pisa

Region: Chianti, Tuscany, Italy

This 10-hour day trip from Pisa to Siena and San Gimignano allows you to spend a day discovering two enchanted Tuscan towns. Savor a wine tasting while exploring the allure of these ancient medieval cities.

Why we love this tour: If you haven’t seen the movie ‘Tea with Mussolini,’ then you should before joining this trip. They filmed at one of the shops in San Gimignano.

From $175.21

San Gimignano: Original & Fun Wine Tour in Chianti by TukTuk

Region: Chianti, Tuscany, Italy

On a traditional Ape Calessino, an Italian tuk-tuk with three wheels, tour the Tuscan countryside near San Gimignano. Leave the Poggibonsi, which are close to San Gimignano and Siena, and go through the Chianti hills and Tuscany’s expansive roadways, passing by rural homes, cypress forests, and vineyards. After that, make a stop at a nearby winery for a traditional Tuscan lunch and tastings of wine and olive oil.

Why we love this tour: This trip was really fun since it was my first time riding a tuk-tuk. It was very easy to see the scenery while feeling the breeze from the wind. It’s a core memory for me.

From $220.39

Chianti Half-Day Wine Tour in the Tuscan Hills, Small Group from Lucca

Region: Chianti, Tuscany, Italy

Take a leisurely half-day tour from Lucca to sample real Tuscan wine directly from the source. Try some sweet, white, and red wines, as well as regional goods like extra-virgin olive oil. Discover the processes involved in producing some of the most sought-after wine in the world and learn about classic wine production techniques.

Why we love this tour: You can have lunch at one of the wineries, and it was fantastic!

From $98.07

Get The Best Of Chianti Wine Tours

A visit to Chianti is incomplete without indulging in the local nectar, and what better way to do so than by joining a delightful wine tour and tasting? Imagine the joy of sipping on velvety Chianti Classico while basking in the warm Tuscan sun, surrounded by panoramic views of lush landscapes.

Whether you’re a wine enthusiast or just eager to experience the authentic flavors of Italy, Chianti’s wine tours offer a welcoming embrace into the world of Sangiovese and culinary delights.

Let the charming villages, delectable cuisine, and the clink of glasses filled with exceptional wine create core memories for you like they did for me!

Wine Tastings And Tours in Chianti FAQs