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Top Tuscany Wine Tastings

We’re committed to helping you feel confident as you get back out there. Check out our flexible cancellation policies and learn what steps operators are taking to keep you safe. As conditions evolve, check local regulations for the latest information.

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975 Tuscany Wine Tastings | All Tuscany Tours

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Private Tour in the Land of the Super Tuscan Wines - Exclusive Bolgheri in a DayDay Trips

Private Tour in the Land of the Super Tuscan Wines - Exclusive Bolgheri in a Day

star-5
Expand your palate in Bolgheri and Castagneto Carducci on a private 10-hour wine tour from Florence. The full-day excursion is perfect for travelers in search of an exclusive and luxurious experience. Your private chauffeur takes you along the famous Via Bolgherese to the Tuscan Coast, which often gets overlooked by foreign visitors. Enjoy tastings at two distinct wineries, along with a traditional lunch, before return to your hotel.
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  • 10 hours
  • Free Cancellation
  • Taking safety measures
From  
$420.07 
Price varies by group size
From  
$420.07 
Price varies by group size
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  • 10 hours
  • Free Cancellation
  • Taking safety measures

Tuscany Vespa TourWine Tastings

SPECIAL OFFER

Tuscany Vespa Tour

star-5
Explore the Tuscan countryside in true Italian style — on a Vespa! After a short van ride from Florence and a riding lesson, spend a full day zipping along scenic country roads from the seat of your own personal Vespa. Pass by historic vineyards, villas and olive groves while your guide shares insight into local history and culture. Tour an organic farm and winery in the famed Chianti Rufina region, where you’ll enjoy a traditional Tuscan lunch and wine tastings.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From  
$143.11 
$178.89
$35.78 savings
From  
$143.11 
$178.89
$35.78 savings
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  • 6 hours
  • Free Cancellation
  • Taking safety measures

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine TastingDay Trips

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

star-4
See the Tuscan gems of San Gimignano, Siena, and Chianti on a day trip from Florence. Stop first in the city the medieval hilltop town of San Gimignano. Then it's off to the village of Chianti for a tasting of local blends and delicious lunch at a winery. Top off your trip in Siena to explore its historic city center with a stop at the Duomo.
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  • 11 hours
  • Free Cancellation
  • Taking safety measures
From  
$80.41 
Price varies by group size
From  
$80.41 
Price varies by group size
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  • 11 hours
  • Free Cancellation
  • Taking safety measures

Maxi Wine Tour San Gimignano Wine Tasting - San Quirico WineryWine Tastings

Maxi Wine Tour San Gimignano Wine Tasting - San Quirico Winery

star-5
The ideal treat for wine aficionados, this special tasting excursion gives you exclusive access to San Quirico Winery, overlooking the stunning hill town of San Gimignano. Sample five organic labels, including Chianti and Vernaccia, and enjoy a tasty market lunch composed of local meats, cheeses, and breads. Small-group tours also included a guided visit of the winery’s cellars and a behind-the-scenes look at the winemaking process.
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  • 1 hour
  • Free Cancellation
From  
$21.60 
Price varies by group size
From  
$21.60 
Price varies by group size
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  • 1 hour
  • Free Cancellation

Small-Group Chianti Wine-Tasting and Castles Trip from SienaDay Trips

Small-Group Chianti Wine-Tasting and Castles Trip from Siena

star-5
Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From  
$228.04 
From  
$228.04 
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  • 8 hours
  • Free Cancellation
  • Taking safety measures

Montepulciano Wine Tasting and LunchDay Trips

Montepulciano Wine Tasting and Lunch

star-5
Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Brunello. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.
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  • 1 to 8 hours
  • Free Cancellation
From  
$279.50 
Price varies by group size
From  
$279.50 
Price varies by group size
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  • 1 to 8 hours
  • Free Cancellation

Siena and Chianti Wineries Excursion by Private Luxury Van from FlorenceDay Trips

Siena and Chianti Wineries Excursion by Private Luxury Van from Florence

star-5
Get a personal introduction to Siena and Chianti with a full-day, private tour from Florence in a luxurious van. Stroll Siena’s gothic streets with a local guide, and discover the art and black-and-white architecture of its UNESCO-listed historic center. Explore rolling vineyards and olive groves then taste your way through famous wineries, family cellars, local olive oils and aged balsamic vinegar.
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  • 8 hours
  • Free Cancellation
From  
$588.10 
per group
From  
$588.10 
per group
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  • 8 hours
  • Free Cancellation

Highlights of Tuscany: Siena, San Gimignano, Chianti, Pisa & Lunch in a WineryDay Trips

Highlights of Tuscany: Siena, San Gimignano, Chianti, Pisa & Lunch in a Winery

star-4
Visit the highlights of Tuscany in a single day on a tour from Florence. Explore Pisa, Chianti, San Gimignano, and enjoy a guided walking tour and entrance ticket to the cathedral Siena. Then visit a family-run Chianti winery for a traditional Italian lunch accompanied by a Chianti tasting. 
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  • 12 hours
  • Free Cancellation
  • Taking safety measures
From  
$105.62 
From  
$105.62 
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  • 12 hours
  • Free Cancellation
  • Taking safety measures

VIP - Tuscan Castle and Ancient Cellars Visit with Wine Tasting near FlorenceWine Tastings

VIP - Tuscan Castle and Ancient Cellars Visit with Wine Tasting near Florence

star-5
Explore the history and flavors of Tuscany with a tour of a 900-year-old castle and winery. Learn about the history of the estate and the Italian family that has lived here for generations on a tour of the castle courtyard, grounds and some private rooms. Then, descend to the ancient wine cellars to learn about traditional production methods and taste four different wines produced on site, paired with a snack of local products like extra-virgin olive oil, salami and cheese. Upgrade to include an authentic Tuscan dinner served at the castle’s restaurant.
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  • 2 hours
  • Taking safety measures
From  
$82.81 
From  
$82.81 
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  • 2 hours
  • Taking safety measures

Dinner and Wine Tasting in Original Tuscan FarmhouseDining Experiences

Dinner and Wine Tasting in Original Tuscan Farmhouse

star-4
Delight your senses with this gourmet food and wine experience at a centuries-old Tuscan farmhouse. Travel through the rolling vineyards and olive groves of the countryside near Florence to arrive at a working farm and winery in the famed Chianti region. Meet resident animals and tour the historic grounds, and then enjoy a fresh, farm-to-table dinner of local specialties accompanied by a tasting of different wines like Chianti and prosecco. For a truly immersive meal, you can even help out in the kitchen if you wish.
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  • 4 hours
  • Free Cancellation
From  
$121.86 
From  
$121.86 
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  • 4 hours
  • Free Cancellation

Siena, San Gimignano, Monteriggioni and Chianti Wine Tasting Tour from FlorenceDay Trips

Siena, San Gimignano, Monteriggioni and Chianti Wine Tasting Tour from Florence

star-4
Combine medieval gems, fine wines, and UNESCO-listed monuments on this full-day tour of central Tuscany from Florence. Marvel over the medieval castle of Monteriggioni; explore the architectural wonders of historic Siena; and admire the striking skyline of hilltop San Gimignano. Enjoy a light lunch in Siena and finish your tour with a wine tasting at a local winery in the Chianti region.
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  • 10 to 11 hours
  • Free Cancellation
  • Taking safety measures
From  
$80.41 
From  
$80.41 
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  • 10 to 11 hours
  • Free Cancellation
  • Taking safety measures

Pisa, Siena and San Gimignano Day Trip from Florence Including LunchDay Trips

Pisa, Siena and San Gimignano Day Trip from Florence Including Lunch

star-4
See all that Tuscany has to offer on this day trip to Pisa, Siena, and San Gimignano from Florence. Led by an expert guide, explore the main square and Gothic cathedral in Siena, followed by a traditional, 3-course lunch with wine. Afterward, enjoy free time to stroll the medieval streets of San Gimignano independently, as well as the city of Pisa, famous for its UNESCO-listed Leaning Tower. Your full day of sightseeing concludes with transportation back to Florence.
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  • 12 hours
  • Free Cancellation
  • Taking safety measures
From  
$79.21 
From  
$79.21 
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  • 12 hours
  • Free Cancellation
  • Taking safety measures

Typical Chianti Villages San Gimignano and Wine Roads by MinivanDay Trips

Typical Chianti Villages San Gimignano and Wine Roads by Minivan

star-4.5
Spend a day in the Tuscan countryside with this day trip from Florence to San Gimignano and the Chianti area, including a wine tasting. Enjoy a stroll in the charming town of San Gimignano before trying wine at a local farmhouse. Then, explore Greve in Chianti and visit some local food shops.
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  • 6 hours 30 minutes
  • Free Cancellation
From  
$142.82 
From  
$142.82 
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  • 6 hours 30 minutes
  • Free Cancellation

Delicious Florence: Evening Food Tour with Wine Tasting & Florentine SteakWine Tastings

Delicious Florence: Evening Food Tour with Wine Tasting & Florentine Steak

star-4
Taste the traditional flavors of Florence with this evening walking tour. Meet local artisans including bakers and chefs as you explore the city’s bustling food scene. Limited to 14 people, this small group tour has five tasting stops including a classic dinner with Florentine steak. Learn about Tuscan wine pairings and sample local delicacies like truffles.
...  More
  • 3 hours 30 minutes
  • Free Cancellation
From  
$95.90 
From  
$95.90 
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  • 3 hours 30 minutes
  • Free Cancellation

Chianti and Castle Tour from SienaDay Trips

Chianti and Castle Tour from Siena

star-4.5
Take the stress out of planning a day in Tuscany on this half-day small-group tour of the Chianti wine region from Siena, including transport. Enjoy an air-conditioned ride over to two popular wineries to taste wines and oils locals love. Plus spend some free time in Monteriggioni, and catch a glimpse of the town’s well-known medieval castle.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From  
$84.01 
From  
$84.01 
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  • 5 hours
  • Free Cancellation
  • Taking safety measures

Escorted Tour: Chianti Winery, Montefioralle, and Greve in ChiantiDay Trips

Escorted Tour: Chianti Winery, Montefioralle, and Greve in Chianti

star-4.5
Get a personalized tour of the Chianti region during this half-day private excursion from Florence. With just your group and dedicated guide, explore the market town of Greve in Chianti and the Castle of Montefioralle, then pop into a local winery to learn about the local Sangiovese grapes and sip some Chianti. Wine tasting and round-trip private transportation from a meeting point near the Florence train station included, or arrange hotel pick-up.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From  
$94.82 
Price varies by group size
From  
$94.82 
Price varies by group size
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  • 5 hours
  • Free Cancellation
  • Taking safety measures

Tuscany Cheese and Wine-Tasting in FlorenceWine Tastings

Tuscany Cheese and Wine-Tasting in Florence

star-3
Become an expert on Tuscan wine and cheese during a 1-hour tasting. Set in an historic wine cellar in the heart of the city, you get a truly authentic Florentine experience. Learn all about the Tuscan wine making process from your sommelier guide. Then taste world-renowned Chianti Classico Riserva, Brunello di Montalcino, and more. The prestigious reds are accompanied by bruschetta, cured meats, and regional cheeses.
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  • 45 minutes to 1 hour
  • Free Cancellation
From  
$46.75 
From  
$46.75 
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  • 45 minutes to 1 hour
  • Free Cancellation

Pienza & Montepulciano - Cities, Cheese & Wine TourDay Trips

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
  • Free Cancellation
From  
$279.50 
Price varies by group size
From  
$279.50 
Price varies by group size
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  • 1 to 8 hours
  • Free Cancellation

Small-Group Dine Around Florence: An Authentic Evening Food and Wine ExperienceWine Tastings

Small-Group Dine Around Florence: An Authentic Evening Food and Wine Experience

star-4.5
Learn to eat and drink like a local Florentine on this tasting tour through Tuscany’s most famous city. Sample Italian wine straight from the barrel at an ‘enoteca,’ and snack on favorite regional products like olives, crostini, cured meats and cheeses. You'll taste authentic Tuscan soup before indulging in a decadent first and second course. Finish on a sweet note with Italian coffee and gelato on this small-group tour limited to 12 people.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From  
$99.62 
From  
$99.62 
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures

Flavors of Lucca Small Group Tour with Food Tasting and WineWine Tastings

Flavors of Lucca Small Group Tour with Food Tasting and Wine

star-5
Discover Lucca’s rich history and local culture through your taste buds on a walking food tour. Follow you guide — and your senses — through the atmospheric city center inside the Renaissance walls, hearing tales from the city’s past while stopping to sample sweet and savory delicacies. Try espresso and cake at a café, fine chocolate treats at a confectioner’s shop, and products found in a typical Luccan lunch like cheeses and cured meats. Top it all off with a glass of regional wine or beer.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From  
$78.01 
From  
$78.01 
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENADay Trips

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

star-5
Explore southern Tuscany with your own private guide on a full-day wine and food tour from Siena. Visit Pienza, Val d'Orcia, Montalcino, and more as you take in small towns, a 14th-century monastery, and sample Brunello di Montalcino, the famous wine of the region. Ride in comfort in a luxury Mercedes vehicle with a private guide who shares the best of the region.
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  • 8 hours
  • Free Cancellation
From  
$271.28 
Price varies by group size
From  
$271.28 
Price varies by group size
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  • 8 hours
  • Free Cancellation

Small-Group Tuscany By VespaDay Trips

Small-Group Tuscany By Vespa

star-4.5
Soak up a unique view of Tuscany on this Vespa tour departing from Florence. Led by an expert guide, journey out of the city and hop onto your scooter once you reach the beautiful country roads of Chianti. Stop for a traditional Tuscan meal at a Farmhouse, you’ll enjoy a tasting of local olive oils and prominent Chianti wines while visiting a famous winery. Your Vespa tour will conclude back at your original departure point in Florence.
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  • 7 hours
  • Free Cancellation
  • Taking safety measures
From  
$148.99 
From  
$148.99 
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  • 7 hours
  • Free Cancellation
  • Taking safety measures

Small-Group Truffle Hunting and Wine Experience from Florence with LunchDay Trips

Small-Group Truffle Hunting and Wine Experience from Florence with Lunch

star-5
Follow your guide on a truffle hunt on this adventure from Florence. Travel by coach to the hilly landscape surrounding San Miniato, a Tuscan town famous for its delectable white truffle. With the help of an experienced hunter and his trusty dog, make your way through the woodland, scanning the earth for this regional specialty. Afterward, reward your search with a 2-course lunch in Chianti, including a wine tasting and truffle pasta. Your small-group tour is limited to eight people and concludes with transportation back to Florence.
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  • 7 hours
  • Free Cancellation
From  
$293.80 
From  
$293.80 
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  • 7 hours
  • Free Cancellation

Private Chianti wine tour leaving from FlorenceWine Tastings

Private Chianti wine tour leaving from Florence

star-5
Spend the day sampling and shopping for wines in the Tuscan countryside during this full-day tour designed with wine-lovers in mind. Travel through medieval villages to the Chianti wine region to Greve to explore and visit the local Wine Museum. Enjoy a cellar tour where you’ll taste Vin Santo, Tuscany’s famous dessert wine, in picturesque Panzano. See the wine shops of Castellina and visit another winery in this iconic region.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From  
$300.05 
Price varies by group size
From  
$300.05 
Price varies by group size
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  • 8 hours
  • Free Cancellation
  • Taking safety measures

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