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Top Chianti Wine Tasting & Winery Tours

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48 Chianti Wine Tasting & Winery Tours

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You can reserve your spot today and pay when you're ready.Learn more

Brunello Vineyards Bus TourWine Tasting & Winery Tours

Brunello Vineyards Bus Tour

star-5
Discover the wines of Montalcino on a 3-hour wine tour that visits two wineries in the region. Enjoy wine tastings and tours of the vineyards, gaining insight into the history of the famous Brunello di Montalcino wine. Travel with a small group limited to eight people and enjoy viewing the picturesque countryside along the way.
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  • 3 hours
From  
US$106.83 
Price varies by group size
From  
US$106.83 
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  • 3 hours

Heart of Chianti Classico - 2 Wineries Lunch included - Chianti Wine TourDay Trips

Heart of Chianti Classico - 2 Wineries Lunch included - Chianti Wine Tour

star-4
Discover the heart of the Chianti region—Chianti Classico—on this day tour from Siena or Florence. Traveling by Mercedes minivan limited to eight people, you'll get to know one of Italy's most famous wine regions as you visit three wineries, partake in tastings of more than 15 wines, and fill up on an included lunch.
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  • 1 to 8 hours
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  • Free Cancellation
From  
US$256.21 
Price varies by group size
From  
US$256.21 
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  • 1 to 8 hours
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  • Free Cancellation

Pienza & Montepulciano - Cities, Cheese & Wine TourDay Trips

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Pienza & Montepulciano - Cities, Cheese & Wine Tour

star-5
Home to medieval hilltop towns and fertile vineyards, Tuscany is widely considered the jewel in Italy’s crown. On this tour, visit the beautiful Tuscan towns of Pienza and Montepulciano, and enjoy a complete immersion in authentic Italian culture and cuisine. With travel from your Chianti, Florence, or Siena hotel, sample local wines in historic cellars and savor a delicious lunch in a traditional Montepulciano winery.
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  • 1 to 8 hours
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  • Free Cancellation
From  
US$255.69 
Price varies by group size
From  
US$255.69 
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  • 1 to 8 hours
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  • Free Cancellation

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Private Truffle hunt in Tuscany from FlorenceDay Trips

Private Truffle hunt in Tuscany from Florence

star-4.5
Set out on a hunt for the elusive truffle on this 6-hour private tour from Florence. Traverse the forest with an official truffle hunter and his dog to learn everything there is to know about this delicacy. After you work up an appetite, sit down to a delicious 3-course truffle lunch accompanied with four wines from a local farm to complete your truffle experience.
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  • 6 hours
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  • Free Cancellation
From  
US$263.50 
Price varies by group size
From  
US$263.50 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Chianti and San Gimignano - 3 Wineries and LunchDay Trips

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Chianti and San Gimignano - 3 Wineries and Lunch

star-5
When visiting Florence, spend a delicious day winery hopping in the renowned Chianti wine region. Visit three of the best estates for tastings of Chianti Classico and other top varietals, plus a gourmet lunch of Tuscan specialties. There's also time to soak up countryside culture and history with a stop in San Gimignano or Monteriggioni, two of Tuscany’s best-preserved medieval towns.
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  • 1 to 8 hours
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  • Free Cancellation
From  
US$250.82 
Price varies by group size
From  
US$250.82 
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  • 1 to 8 hours
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  • Free Cancellation

Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from FlorenceDay Trips

Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

star-5
Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied by one of our expert English speaking drivers born and raised in Tuscany. -During the 8/9hr tour you will explore the Gothic city of Siena with its famous shell-shaped Piazza del Campo and the gorgeous cathedral, followed step by step by a licensed TOUR GUIDE! -In the afternoon you will have the opportunity to visit some of the most famous vineyards, or unknown small family businesses, see their cellars and taste their excellent wines and food. -Then explore the wonderful medieval city of San Gimignano. Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs.
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  • 9 hours
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  • Free Cancellation
From  
US$790.51 
per group
From  
US$790.51 
per group
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  • 9 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse from FlorenceWine Tasting & Winery Tours

Grape stomping in Tuscan farmhouse from Florence

star-5
Get ankle deep in Tuscan tradition on a half-day grape stomping tour from Florence.  Private transportation will take you from your hotel to a winery in the Chianti hills. There, you’ll explore the history and modern practices of winemaking. After tromping on the locally grown grapes, replenish your strength with a homemade lunch and wine tasting, before returning to your accommodation.
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  • 3 hours
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  • Free Cancellation
From  
US$274.48 
Price varies by group size
From  
US$274.48 
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  • 3 hours
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  • Free Cancellation

Off-Road Tuscan Wine Tour from ChiantiWine Tasting & Winery Tours

Off-Road Tuscan Wine Tour from Chianti

Go off-road in a vintage SUV on this Chianti Valley tour from Greve. With a small group of just eight people or fewer, travel through the famous wine-producing region to learn the vintners' secrets. Stop at three cellars for 15 tastings of different varietals as well as local products (olive oil, honey) and a traditional Italian lunch.
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  • 4 hours
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From  
US$307.42 
Price varies by group size
From  
US$307.42 
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  • 4 hours
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  • Free Cancellation

Poggio al Sole - Organic Winery in Chianti ClassicoDining Experiences

Poggio al Sole - Organic Winery in Chianti Classico

star-5
The visit on Poggio al Sole will take you to one of the nicest wineries in the Chianti Classico area with a stunning view over the famous rolling tuscan hills. You will see a traditional house built centuries ago still home to the farmers family and get to sit in their garden and enjoy the peaceful nature and the breathtaking view.
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  • 2 hours
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  • Free Cancellation
From  
US$23.81 
From  
US$23.81 
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  • 2 hours
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  • Free Cancellation

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing LunchDay Trips

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Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

star-5
Leave the planning and driving to someone else on this daylong winery tour specializing in Brunello di Montalcino—a wine produced in the vineyards around the town of Montalcino. Visit historic wine cellars and vineyards, have lunch in a winery in the hill town of Montalcino itself, and visit a winery in the nearby Nobile di Montepulciano area for good measure.
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  • 1 to 8 hours
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  • Free Cancellation
From  
US$251.43 
Price varies by group size
From  
US$251.43 
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  • 1 to 8 hours
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  • Free Cancellation

Great wine tour in Tuscany From FlorenceDay Trips

Great wine tour in Tuscany From Florence

star-5
Booking a private wine-tasting tour in Tuscany means personalized attention and a flexible itinerary. With a dedicated guide, you'll go in-depth to understand Italian wine production on two winery visits and a total of six tastings. Round-trip transportation means no need to worry about who will be the sober driver; you'll round out the day with a typical Tuscan lunch.
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  • 6 hours
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  • Free Cancellation
From  
US$274.48 
Price varies by group size
From  
US$274.48 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Montalcino and Montepulciano Wine Tour from SienaDay Trips

Montalcino and Montepulciano Wine Tour from Siena

Explore the Val d'Orcia Region of Tuscany on a private, full-day tour. Stop in Montepulciano to soak up the history of the medieval town and visit a winery where you taste the region’s wines. Sit down for a traditional Tuscan lunch before continuing on to Pienza, a fifteenth-century village filled with antique shops and known to be the birthplace of Pecorino cheese. Finally stop in Montalcino and tastethe sought after Brunello di Montalcino wines while you admire the vineyards and olive groves.
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  • 6 hours
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  • Free Cancellation
From  
US$450.15 
Price varies by group size
From  
US$450.15 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Greve in Chianti Wine Tasting and Winery TourDining Experiences

Greve in Chianti Wine Tasting and Winery Tour

star-5
For true wine-lovers, there’s no greater thrill than seeing where Tuscany’s specialty red is made. During this in-depth tour of an organic, family-run winery, you’ll learn the ins and outs of Chianti Classico. Tour the scenic vineyard and sample four different red wine varieties inside the atmospheric on-site cellar. Pair your tasting with fresh cheeses and salami, all made from fresh regional products.
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  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$49.41 
From  
US$49.41 
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  • 1 hour 30 minutes
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  • Free Cancellation

Wine tour with a SommelierDay Trips

Wine tour with a Sommelier

Take an in-depth tour of the Tuscan wine regions with a certified expert. Your private guide on this journey is a sommelier who is very familiar with the wines and wineries of the area. Spend the day touring two or three wineries, with samplings at each. A delicious Italian lunch at an organic farm is also included. No need to worry about a designated driver, as pickup and drop-off can be included.
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  • 5 hours
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  • Free Cancellation
From  
US$258.01 
Price varies by group size
From  
US$258.01 
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  • 5 hours
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  • Free Cancellation

Horseback Riding Tour with wine tasting from SienaDining Experiences

Horseback Riding Tour with wine tasting from Siena

star-5
See the Chianti region’s famous vineyards, olive groves, and medieval villages from an entirely new perspective when you embark on a half-day horseback riding tour. This private tour begins with pickup from your Siena accommodation; travel by car to an area winery, where the adventure begins. Once you’ve become acquainted with your horse, you’ll ride past some of the area’s loveliest scenery. Finish with a traditional Tuscan lunch, plus wine tasting.
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  • 5 hours
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  • Free Cancellation
From  
US$263.50 
Price varies by group size
From  
US$263.50 
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  • 5 hours
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  • Free Cancellation

Private wine tour of Chianti (chauffeured)Wine Tasting & Winery Tours

Private wine tour of Chianti (chauffeured)

star-3
Avoid the hassle of navigating the rural roads and trying to locate the small cellars in Tuscany’s wine country with this wine tour that includes round-trip transportation. Stop for a tour and tasting at one or two scenic wineries near Siena before a lunch break. In the afternoon, visit cellars in Montalcino or the Val d’Arno to sample some of Tuscany’s most historic labels.
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  • 6 hours 45 minutes
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  • Free Cancellation
From  
US$192.14 
Price varies by group size
From  
US$192.14 
Price varies by group size
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  • 6 hours 45 minutes
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  • Free Cancellation

Luxury Montalcino wine tourDay Trips

Luxury Montalcino wine tour

Discover the fine wines of Montalcino, a small town nestled in the hills of Tuscany. After pick-up from the doorstep of your Florence accommodation, your private driver transports you to a vineyard that uses music to age their natural wines. Continue on to Castel Giocondo for a second tasting, followed by a 3-course lunch prepared by Michelin-rated chef Massimo Rossi. Enjoy the meal against a backdrop of the Tuscan countryside.
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  • 6 hours
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  • Free Cancellation
From  
US$603.86 
Price varies by group size
From  
US$603.86 
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  • 6 hours
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  • Free Cancellation

Luxury Maremma wine tourDay Trips

Luxury Maremma wine tour

Get to know the off-the-beaten-path wine region of Maremma, in coastal Tuscany, during this private tour. Round-trip private transportation is convenient and means that you can taste as much wine as you wish. Visit two wineries, both known for their modern architecture, to taste samples and learn about wine production. You'll also enjoy a 3-course lunch and wine pairing.
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  • 6 hours
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  • Free Cancellation
From  
US$625.82 
Price varies by group size
From  
US$625.82 
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  • 6 hours
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  • Free Cancellation

Tour and Tasting at an Organic Winery in the Heart of Chianti Classico AreaWine Tasting & Winery Tours

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

star-5
Sip some of Italy's most famous wine during a 1.5-hour visit to an organic winery in the heart of the Chianti region. Tour the vineyards and organic winery between Radda and Panzano, right in the Chianti Classico wine-producing area. Learn about how local wines are made. Take part in a wine-tasting session at the conclusion of your tour, sampling between 3-6 wines with appetizers such as bread with olive oil produced on-site.
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  • 2 hours
  • Free Cancellation
From  
US$29.68 
From  
US$29.68 
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  • 2 hours
  • Free Cancellation

Montalcino and Pienza Tuscany Wine&Cheese Fullday from RomeDay Trips

Montalcino and Pienza Tuscany Wine&Cheese Fullday from Rome

Don’t miss the opportunity to experience the unique beauty and ambiance of Tuscany during your Italian holiday. Discover Montalcino, Pienza, and Montepulciano on a private 12-hour tour from Rome. Along with a comfortable and scenic journey, your private chauffeur also provides insider information about all three location. Each known for wine production, the towns also boast a host of scenic landmarks and distinct culture that sets them apart from one another.
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  • 12 hours
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  • Free Cancellation
From  
US$340.36 
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From  
US$340.36 
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  • 12 hours
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  • Free Cancellation

Winery Tour in a Castle in TuscanyWine Tasting & Winery Tours

Winery Tour in a Castle in Tuscany

Sip wine during a visit to a medieval Tuscan castle in the Chianti Classico region. The express wine-tasting tour includes a visit to the castle’s vineyard and a centuries-old cellar where the esteemed Chianti Classico wine is aged. You’ll learn about viticulture and fermentation as you savor sips of four types of wine, along with extra virgin olive oil and a rich balsamic vinegar.
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  • 1 hour
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  • Free Cancellation
From  
US$24.07 
From  
US$24.07 
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  • 1 hour
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  • Free Cancellation

Luxury Chianti Classico ExperienceDay Trips

Luxury Chianti Classico Experience

star-5
Delve into the heart of Tuscany’s Chianti wine region—and enjoy an indulgent meal plus wine tastings—when you book this private, half-day tour. Following pickup at your area hotel, set off with just a private guide for company. Venture first to the Antinori nel Chianti Classico winery, where you’ll tour the striking facilities and enjoy a tutored tasting. Then, transfer to the regal Villa Le Corti for further wine and olive oil tastings, plus a gourmet, 3-course lunch.
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  • 6 hours
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  • Free Cancellation
From  
US$603.86 
Price varies by group size
From  
US$603.86 
Price varies by group size
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  • 6 hours
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  • Free Cancellation

Walk the Saturday Market & Organic food guided-tastingWine Tasting & Winery Tours

Walk the Saturday Market & Organic food guided-tasting

star-5
In my village, Greve in Chianti, you can visit one of the most characteristic Food Market of Tuscany. The Greve's square host the Saturday market from about 1000 years! I will introduce major themes in Tuscan cuisine and give you background in the evolution of this area as a wine & food center. In the market, we will see, smell, and savor the fresh, locally-sourced meat and vegetables, cheeses, bread, and baked goods. We will discuss the importance of eating what is "di stagione" (seasonal). I will teach you some traditional Chianti recipes, simple and made with few ingredients, that I learned from my grandmother Anna. Not just a look: after the market visit we will back at the Wine Lovers Academy, where we will have a tasting lesson about the traditional Tuscan food: from Pecorino cheese to the artisanal salami, Chianti Olive Oil, Honey, and truffle! I'm waiting for you here in G​reve to let you discover all the secrets of our beautiful​ land!
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  • 2 hours
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  • Free Cancellation
From  
US$30.46 
From  
US$30.46 
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  • 2 hours
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  • Free Cancellation

Tuscan Wine and Food Pairing ExperienceWine Tasting & Winery Tours

Tuscan Wine and Food Pairing Experience

star-5
Use your senses to learn the fine art of food and wine pairing with a short lesson in the Tuscan hill town of Greve-in-Chianti. Taste three fine Tuscan wines along with regional specialties like salami and cheeses. With the help of a gourmet guide, take notes and learn to identify flavor characteristics like “assonance” and “contrast” so you can confidently choose wine pairings back home.
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  • 50 minutes
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  • Free Cancellation
From  
US$20.04 
From  
US$20.04 
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  • 50 minutes
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  • Free Cancellation


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