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Last updated: 24 June, 2023
Expert travel writer: Nicky Swallow

Some of Italy’s best wines are produced in the DOCG Chianti Classico, 177,500 acres of undulating, vine-striped land stretching between Florence and Siena. Dozens of wine estates share this fertile terroir, many of which offer tastings and vineyard tours and an opportunity to buy wines from source. Some also have very good restaurants and accommodation.

The history of wine-making in the region dates back hundreds of years. Early Chiantis were a blend of Sangiovese, Canaiolo and Malvasia Bianca grapes; today, a DOC Chianti must be made with at least 80% Sangiovese.

The main Chianti growing area is divided into eight sub-zones. The most famous is Chianti Classico, located between Florence and Siena, which produces some 25 million bottles a year, including some of the region’s greatest wines. Most bottles sport the image of a black rooster on a gold background, a guarantee of quality.

While you’re there

Many of the wine estates in Chianti also produce excellent olive oil, which you can taste along with the wines and purchase on site. Among the best are Castello di Ama, Dievole, Fonterutoli, Badia a Coltibuono and Borgo San Felice.

Brancaia

Radda, Tuscany, Italy

Brancaia

A Swiss-owned Brancaia winery located near Castellina-in-Chianti. As well as cellar tours and tastings, they offer a ‘Blending Experience’ with the sommelier.

Best for ages 18+

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Castellina in Chianti

Castellina in Chianti, Tuscany, Italy

Castellina in Chianti

Lying directly on the SS222, hill-top Castellina was once a bastion of Florentine dominance as seen in the imposing fortifications and tower. It’s a very pleasant town to wander around and there are lots of places to buy and taste wine.

Best for ages 18+

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Castello di Ama

Gaiole, Tuscany, Italy

Castello di Ama

Ama is a tiny stone hamlet near Gaiole in a glorious setting. Apart from superb wines, Ama has an excellent restaurant, four lovely suites and one of the most important collections of site-specific artworks in Italy.

Best for ages 18+

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Castello di Fonterutoli

Fonterutoli, Tuscany, Italy

View of the picturesque village of Fonterutoli, province of Siena, Tuscany, Italy, surrounded by vineyards, olive groves and cypresses.

The aristocratic Marchesi Mazzei family have been making wine at Fonterutoli since the 11th century; it now boasts a state-of-the-art wine cellar where you can book tours and tastings. The superb wines pair well with the elegant-rustic dishes on offer at the Osteria.

Best for ages 18+

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Greve

Greve, Tuscany, Italy

Greve

Medieval Greve-in-Chianti lies at the northern end of the Chianti Classico area and is a bustling market town with pretty arcaded central piazza. Generally considered the centre of Chianti wine-making, it hosts a huge, annual Festa del Vino, usually on the second weekend of September.

Best for ages 18+

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Price: Free
Minimum age: Any
Age suitable: 18+
When: All year around

Getting there & doing it

The ‘wine towns’ of Greve-in-Chianti and Castellina-in-Chianti are good starting points and the tourist offices have maps. The Chianti Classico Consortium’s website has information about the opening hours of each estate and the tours and tastings they offer.

Most tastings and vineyard tours need to be booked ahead. The distances between the northern and southern confines are longer than expected and the roads are winding; choose three or four to visit that are close together.

Self-drive means you can stop and start when you like, but organised tours are often a simpler option, with tours and tastings all pre-arranged.

When to do it

Wine estates are open all year round seven days a week. It’s interesting to visit during September when the vendemmia (grape harvest) is underway although some smaller estates discourage visitors in this period.

Our selection of the best Viator tours of this attraction or activity

Discover Chianti Through its Wines

Florence

Discover Chianti Through its Wines
Located between Florence, Siena and San Gimignano, Casa Sola is a family owned boutique winery, ideal stop for those who want to discover the magic of Chianti world. Our passionate team is ready to share with you the history of the area, we will illustrate Casa Solas' vision and lets you discover the quality and the diversity of Chianti Classico wines. Learn the story behind the production of each bottle of wine, from the time of the pruning, to the vendemmia or harvest, through the fermentation and aging.  Learn what makes each vintage different and delicious.

Price: €34

Min age: 0

Rating 4.98 / 5 [81 ratings]

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Skip the Line: Siena Duomo and City Walking Tour

Siena

Skip the Line: Siena Duomo and City Walking Tour
Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and visit the stunning Siena Duomo (Siena Cathedral) with your fast-track, skip-the-line entrance ticket. As you walk through this incredibly beautiful Tuscan city with your expert guide, you'll feel as though you’ve journeyed back in time.

Price: €35

Min age: 0

Rating 4.75 / 5 [418 ratings]

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Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area

Chianti

Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area
Visit an organic estate that organizes guided tour and tastings in the heart of Chianti Classico area, between Radda and Panzano in Chianti. During the tour it is possible to see the vineyards and the wineries, hear a guided explanation of the wine-making process in order to make wines of the highest quality. The visit is then followed by the tasting of the 3 or 6 wines, accompanied by small but tasty snacks, including bread with olive oil of own production and Grappa.

Price: €40

Min age: 18

Rating 4.91 / 5 [103 ratings]

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Greve in Chianti Wine Tasting and Winery Tour

Chianti

Greve in Chianti Wine Tasting and Winery Tour
Visit a small family winery, where products are organic, the company's coverage is 1 hectare of olive grove and 3 of Sangiovese, Syrah and Merlot wines. The visit starts from the vineyard next to the winery with an explanation of the history of Chianti Classico, and then moved in the olive. Subsequently, you will be made to access the cellar, where you will learn all the processes of production of the Chianti Classico wine.

Price: €50

Min age: 0

Rating 4.74 / 5 [103 ratings]

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Chianti Wine Tour from Florence

Florence

Chianti Wine Tour from Florence
A comprehensive experience in one of the most fascinating areas of Tuscany, known all over the world for its wine and its countryside of unrivalled charm, where woods alternate with vineyards and olive groves, in a landscape dotted with Romanesque parish churches, farmhouses, villas and castles of rare beauty. You have the chance to combine Chianti wine with blissful Tuscan countryside on a Wine tour from Florence! With your tour escort, travel out of Florence and spend your time tasting the famous Chianti Wines and the typical Food in two enchanting wineries with local wine-expert guides, in the Chianti Fiorentino and in the Chianti Senese regions. In both wineries, tour the wine cellars, hear the secrets of Tuscan organic wine making, and then sample prestigious Tuscan wine alongside some traditional Italian snacks.

Price: €55

Min age: 0

Rating 4.24 / 5 [2362 ratings]

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Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme

Montecatini Terme

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme
Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in the beautiful Tuscan countryside. Discover the vibrant local life, the colorful pottery shops and the tallest towers of San Gimignano. In Siena will you will learn all the secrets about the famous horse race “Palio” and Campo square. A special guided Chianti wine tasting and visit of a famous wine estate will be reserved for you. Small group, more flexibility and attention for you!

Price: €149

Min age: 0

Rating 4.75 / 5 [33 ratings]

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Siena, San Gimignano and Chianti Wine Small Group from Lucca

Lucca

Siena, San Gimignano and Chianti Wine Small Group from Lucca
Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in the beautiful Tuscan countryside. Discover the vibrant local life, the colorful pottery shops and the tallest towers of San Gimignano. In Siena will learn all the secrets about the famous horse race “Palio” and Campo square. A special guided Chianti wine sampling and the visit of a famous wine estate will be reserved for you. Small group, more flexibility and attention for you.

Price: €149

Min age: 0

Rating 4.52 / 5 [17 ratings]

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Florence Sightseeing Walking Tour with a Local Guide

Florence

Florence Sightseeing Walking Tour with a Local Guide
This 2 hour walking city tour will take you to the highlights of the city of Florence led by a local expert guide.  This tour is a great introduction to the city and you will see Santa Croce Church, the Bargello Palace, Piazza della Signoria, Ponte Vecchio, Palazzo Vecchio, the Cathedral, Giotto's Bell Tower, Uffizi Gallery's courtyard, the church of San Lorenzo (all from the outside) . The guide will give you also precious suggestions on how to spend your holiday in Florence and where to eat.

Price: €159

Min age: 0

Rating 4.77 / 5 [84 ratings]

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Chianti Wine Tour with Tuscan Lunch Open Top Van Max 6 pax

Florence

Chianti Wine Tour with Tuscan Lunch Open Top Van Max 6 pax
This is a unique wine tour to discover the beauty of Chianti with the typical scents and colors of this extraordinary land. Thanks to our exclusive minivan, unique to Tuscany, you can explore the Chianti area like never before. Our first stop will be visiting a first winery, where you will taste 4 wines paired with Extra Virgin Olive Oil, tuscan bread local salami and cheese in a unique atmosphere. Then, immersed in the heart of the Chianti area we will visit one of the most enchanting medieval hamlets, Montefioralle. Continue to Greve in Chianti the entrance to the Chianti area, its fame has always been tied to its principal Piazza Matteotti, with little shops under porticos with typical hand-crafted products. The last stop of the tour will be a winery where you will have the chance to enjoy a classic Tuscan lunch accompanied by a fantastic tasting of wines appropriately chosen according to the course

Price: €180

Min age: 6

Rating 4.97 / 5 [71 ratings]

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Private Tour: San Gimignano Walking Tour

San Gimignano

Private Tour: San Gimignano Walking Tour
Enjoy a classic 1.5h hour Private tour through the medieval town of San Gimignano with an experienced local guide. Touch on all the main sites and learn about the town’s rich history and famous products and visit some of the quieter corners of this historical hill town.

Price: €190

Min age: 0

Rating 4.94 / 5 [17 ratings]

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Half-Day Chianti Tour to 2 Wineries with Wine Tastings and Meal

Florence

Half-Day Chianti Tour to 2 Wineries with Wine Tastings and Meal
Enjoy 5.5 hrs round trip from Florence in a comfortable 8-seater van to the wine country with our wine expert's commentary about the region.  Visit 2 family-owned wineries in the Chianti Classico region with guided tastings to 4 wines at each winery. The family owned wineries are located in a beautiful setting with vistas over the Tuscan countryside.  Taste Chianti, Riserva and different Super Tuscan wines. Freshly prepared meal at the second winery included.

Price: €199

Min age: 16

Rating 4.87 / 5 [55 ratings]

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Chianti Classico E-Bike Tour

Siena

Chianti Classico E-Bike Tour
One day bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines and beauty of the landscapes. Chianti offers a unique landscapes: gentle hills covered by vineyards and olive groves, small stone villages and farm houses. We'll start biking in the hearth of Chianti Classico, only 20 minutes from Siena, during the bike tour we will reach the Castle of Brolio, owned by the Ricasoli family since 1141, and the small villages of Villa a Sesta. We will stop then in a local winery for a Chianti wine tour and tasting. The tour includes also the lunch in local restaurant located at Castelnuovo Berardenga.

Price: €220

Min age: 14

Rating 5 / 5 [17 ratings]

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Private Chianti Classico Tour with wine and food tasting in a Historic Estate

Florence

Private Chianti Classico Tour with wine and food tasting in a Historic Estate
The privilege to visit the historical and suggestive cellars of a prestigious estate surrounded by ancient vineyards followed by the exclusive tasting experience of local wines and delicious local food

Price: €248

Min age: 0

Rating 4.54 / 5 [22 ratings]

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Private Tour: Secret Siena Walking Tour

Siena

Private Tour: Secret Siena Walking Tour
Discover the older parts of Siena’s medieval centre and see hidden corners away from the crowded tourist areas, an exceptional itinerary to discover the quieter side of Siena.

Price: €250

Min age: 0

Rating 4.97 / 5 [68 ratings]

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Quad Tour ATV Adventure in Chianti. Lunch and Wine Tasting

Florence

Quad Tour ATV Adventure in Chianti. Lunch and Wine Tasting
Come and discover the wild heart of Chianti, together with us you can live an experience totally immersed in the green of the countryside and woods. You will have fun in total safety by driving on the roads and off-road. After the quad experience you will continue the tour enjoying the landscapes of the Chianti Classico, thanks to our specially modified minivan to fully appreciate the scents and colors of our countryside full of vineyards and olive groves. We will stop to visit Montefioralle, a small and fascinating medieval village of 1100 and Greve in Chianti, whose fame has always been linked to its main Piazza Matteotti, with small shops under arcades with typical artisan products. The last stop of the tour will be a winery where you will taste a classic Tuscan lunch accompanied by a fantastic tasting of 6 wines, chosen appropriately according to the courses.

Price: €260

Min age: 0

Rating 4.86 / 5 [30 ratings]

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SMALL GROUP Chianti 2 wineries & meat feast @ Dario Cecchini

Florence

SMALL GROUP Chianti 2 wineries & meat feast @ Dario Cecchini
This day trip is to explore the flavors of the land just south of Florence with its traditions for great wine, olive oil, cheese & meats. We visit two distinct organic wineries, and you will come to understand the concept of terroir, and you will learn how Chianti & Chianti Classico is made. Your Grape guide will explain how to distinguish the characteristics of the wines in your glass. Lunch is an exceptional feast at famous butcher Dario Cecchini with traditional dishes as well as the iconic Bistecca. Return with the fondest of memories of Tuscany's wine country.

Price: €270

Min age: 18

Rating 4.99 / 5 [159 ratings]

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Private Tour of Chianti Siena and San Gimignano by Minivan

Florence

Private Tour of Chianti Siena and San Gimignano by Minivan
It will be your special day. The driver will be at your disposal and will discuss with you all the possible solutions, so he will be able to customize your day, adapt to your needs and focus only on the attractions that interest you. Start the day with a relaxing visit to the Piazzale Michelangelo where you can take the most beautiful photos of Florence, then after you leave for Siena through the beautiful Tuscan countryside admiring the beauty of the Chianti. Once in Siena we will go directly to the beautiful Piazza del Campo famous all over the world for its beauty, art history and the famous horse race, here in the historic center of Siena you will have free time to. After 2 hours we leave for a visit to the winery where you will discover the secrets of Chianti wine, taste genuine local products. After lunch we continue to visit the medieval village of San Gimignano UNESCO World Heritage Site Famous for its towers ,Here you will have free time to walk in the small old town..

Price: €275

Min age: 0

Rating 4.90 / 5 [65 ratings]

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Exclusive Chianti Classico Day Trip from Florence

Florence

Exclusive Chianti Classico Day Trip from Florence
Do you want to learn more about one of the most prestigious wines in Italy and worldwide? Embark with us on this journey in the land of the famous Black Rooster, in the heart of the Chianti Classico. You will visit 3 family-run wineries and taste an impressive pallet of Chianti wines. You will tour the vineyards and wine cellars, giving an up close look at the production and ageing process. Additionally, you will find out more about the secrets of a cherished Italian ingredient, the extra virgin olive oil. Apart from tasting the best selection of Tuscan Wines produced in boutique wineries, you will serve a typical, multi-course lunch. Wine and food are sacred in Italy and therefore you will receive tips about the art of pairing wine with food.

Price: €419

Min age: 10

Rating 5 / 5 [21 ratings]

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Exclusive Brunello di Montalcino Day Trip from Florence

Florence

Exclusive Brunello di Montalcino Day Trip from Florence
Explore a region renowned internationally for its Brunello di Montalcino, a red wine hard to forget due to its precious formula! Brunello di Montalcino is produced with a local type of Sangiovese grape, referred to as Brunello or Sangiovese Grosso, possessing Italy’s highest DOCG classification. Take some time to enjoy a region rich in refined winemaking and cultural treasures alike. Escape the hustle and bustle of Florence and experience the heart of Tuscany by visiting the enchanting wine region of Montalcino. During the day trip, you will visit 3 family-run wineries and the medieval town of Montalcino. You will taste not only the precious Brunello, but also a wide range of regional wines, such as Rosso di Montalcino. You will have the chance of comparing different styles of winemaking, while enjoying 3 wine tastings at scenic properties in the Montalcino wine area. Traditional Tuscan lunch is provided by one of the wineries, using 0 km products and local specialties.

Price: €449

Min age: 10

Rating 5 / 5 [29 ratings]

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Hot Air Balloon flight in Florence

Florence

Hot Air Balloon flight in Florence
Florence, is known worldwide as the birthplace of Reinassance. By over flying the city of Florence, you cane se the magnificent architecture from up above, and this gives you the possibility to discover every detail of the city from a whole new prospective. NOTE: Flights only take place at sunrise. The exact take-off time will be communicated to you based on the chosen day. We based on the same time as sunrise.

Price: €450

Min age: 6

Rating 4.92 / 5 [52 ratings]

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Exclusive Cinque Terre Private Day Trip from Florence

Florence

Exclusive Cinque Terre Private Day Trip from Florence
Explore the scenic Italian Riviera! Discover one of Italy’s most amazing destinations, the unforgettable Ligurian Coast of Cinque Terre, UNESCO World Heritage site. Enjoy scenic views of the 5 ingeniously constructed fishing villages on this private tour from Florence, accompanied by your own sommelier guide. Between the villages you will enjoy scenic train rides along the Ligurian coastline. A relaxing boat ride is also included between 2 of the villages so you can enjoy stunning views of the Cinque Terre from the water. Wander the narrow streets, admire the colourful houses or take the chance to swim in the turquoise water. A multi-course lunch paired with the aromatic, mineral wine of Cinque Terre will be served in a restaurant overlooking the Mediterranean sea. Cinque Terre remains Italy's most difficult area to cultivate due to unfriendly environmental conditions. Dive into traditional Ligurian food and local specialties, such as seafood dishes and pasta with pesto!

Price: €479

Min age: 12

Rating 4.90 / 5 [62 ratings]

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Private Excursion to Siena, San Gimignano and Chianti Landscapes

Florence

Private Excursion to Siena, San Gimignano and Chianti Landscapes
Discover the beauty of Siena and San Gimignano, traveling through the countryside of the Chianti region, with ever changing scenery of vineyards and olive trees on this full day private trip from Florence.

Price: €488

Min age: 0

Rating 4.77 / 5 [22 ratings]

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Destination guides including or relevant to this experience

Tuscany

Tuscany, Italy

Tuscany

The astonishingly beautiful region of Tuscany has it all: art cities and ancient hill towns, high mountains and long sandy beaches, alongside luxurious hotels and some of Italy’s best food and wine.

Florence

Tuscany, Italy

Florence

A heady mix of incomparable Renaissance art, gorgeous palazzos, Tuscan cuisine and home-grown haute couture.

Siena

Tuscany, Italy

Beautiful view of Dome and campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena in the sunny day, Tuscany, Italy

Arguably the most perfect medieval city in the world, Siena is a glorious ensemble of red brick buildings and exquisite monuments, famous for its fan-shaped Campo and Il Palio horse race.

Round-ups that include this experience

13 Best wine regions

Multiple countries

A bucket full of grapes placed underneath a vineyard plant

The world’s greatest wine regions – where you can sip the world’s greatest wines at source, and tour the vineyards to learn how they’re made.