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Top Chianti Tours & Sightseeing

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Cultural Tours

Grape stomping in Tuscan farmhouse

Participate in the Tuscan tradition of grape stomping on a private four-hour tour in the Chianti hills.  Explore a local vinyard with your private guide and discover the wine making process. In addition to living out your Italian dreams of crushing grapes with your bare feet, you’ll also enjoy a wine tasting, along with a homemade lunch.
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  • 4 hours
  • Free Cancellation
From  
US$108.49
From  
US$108.49
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  • 4 hours
  • Free Cancellation

Cultural Tours

Grape stomping in Tuscan farmhouse from Florence

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
  • Free Cancellation
From  
US$182.72
From  
US$182.72
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  • 3 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Off-Road Tuscan Wine Tour from Castellina

Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at three wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop. The tour starts and ends in the village of Castellina in Chianti.
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  • 4 hours
  • Free Cancellation
From  
US$182.72
From  
US$182.72
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  • 4 hours
  • Free Cancellation

4WD, ATV & Off-Road Tours

Private Truffle hunt in Tuscany from Florence

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
  • Free Cancellation
From  
US$154.17
From  
US$154.17
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  • 6 hours
  • Free Cancellation

Private Sightseeing Tours

Montalcino and Montepulciano Private Tour

Explore the beautiful Val d’Orcia just outside of Florence on this private full-day tour. Drive through the rolling countryside to visit the picturesque towns of Montepulciano, Pienza, and Montalcino. Sample wines from local vineyards and sit down to a delicious lunch made with fresh ingredients from the region. Discover the Tuscany that appears in movies and on postcards during this tour and admire the beautiful landscapes.
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  • 6 hours
  • Free Cancellation
From  
US$296.92
From  
US$296.92
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  • 6 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

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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  • 8 hours
  • Free Cancellation
From  
US$205.56
From  
US$205.56
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  • 8 hours
  • Free Cancellation

Wine Tasting & Winery Tours

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
  • Free Cancellation
From  
US$195.28
From  
US$195.28
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  • 5 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Pienza & Montepulciano - Cities, Cheese & Wine Tour

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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  • 8 hours
  • Free Cancellation
From  
US$205.56
From  
US$205.56
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  • 8 hours
  • Free Cancellation

Vespa, Scooter & Moped Tours

Private VESPA Tour in Tuscany

Experience the Tuscan countryside from a perspective rare to visitors on a private Vespa tour with round–trip transport from your Siena hotel. In addition to navigating for you, your guide ensures the best views and stops for photo opportunities along the way. The day includes a Tuscan–style lunch and complimentary wine tasting with vineyard views.
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  • 6 hours
  • Free Cancellation
From  
US$171.30
From  
US$171.30
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  • 6 hours
  • Free Cancellation

Private Sightseeing Tours

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

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
  • Free Cancellation
From  
US$822.25
From  
US$822.25
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  • 9 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Heart of Chianti Classico - 3 Wineries and Lunch - Chianti Wine Tour

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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  • 8 hours
  • Free Cancellation
From  
US$205.56
From  
US$205.56
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  • 8 hours
  • Free Cancellation

Wine Tasting & Winery Tours

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
  • Free Cancellation
From  
US$342.60
From  
US$342.60
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  • 6 hours
  • Free Cancellation

Private Sightseeing Tours

Private Tour in Val d'Orcia

Discover the natural beauty of Italy's Val d'Orcia on this private tour that introduces you to the postcard-perfect scenery of rolling hills and vineyards. You'll visit the towns of Montepulciano, Pienza, and Montalcino; tour a winery; and enjoy included wine tastings and a Tuscan lunch for a well-rounded experience in this UNESCO World Heritage–listed valley.
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  • 6 hours
  • Free Cancellation
From  
US$199.85
From  
US$199.85
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  • 6 hours
  • Free Cancellation

Bike & Mountain Bike Tours

Bike tour with wine tasting

Bus tours of Tuscany can feel out of touch with the beautiful, rolling countryside that travelers love. This tour allows you to get out of the bus and into the landscapes of the Tuscan countryside on a bike, following routes designed for casual cyclists or professionals. It’s a small-group affair, includes hotel pickup and drop-off, and finishes with a lunch of Tuscan dishes and wine.
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  • 6 hours
  • Free Cancellation
From  
US$148.46
From  
US$148.46
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  • 6 hours
  • Free Cancellation

4WD, ATV & Off-Road Tours

Truffle Hunting with Wine Tasting in Tuscan farmhouse

Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.
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  • 4 hours
  • Free Cancellation
From  
US$137.04
From  
US$137.04
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  • 4 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Chianti and San Gimignano - 3 Wineries and Lunch

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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  • 8 hours
  • Free Cancellation
From  
US$205.56
From  
US$205.56
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  • 8 hours
  • Free Cancellation

Wine 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
  • Free Cancellation
From  
US$205.56
From  
US$205.56
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  • 4 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Luxury Maremma wine tour

Everyone knows Florence, Chianti region, Siena, but have you ever heard of Maremma? We are talking about the coastal area of south-western Tuscany, stretching between the cities of Livorno and Grosseto. This land has been constantly flourishing in the last years, becoming a must when you visit Tuscany: here you can find the perfect combination between human presence and still uncontaminated and wild nature. Thanks to its particular hot, sunny and windy microclimate and to its position close to the coast, wines from this region are something different in the Tuscan panorama, even if grapes cultivation here started many centuries ago. Visit the two most important Maremma wineries, known for their modern design: Rocca di Frassinello and Le Mortelle. Tasting of 3 innovative wines at Rocca di Frassinello owned by Panerai then proceed to Antinori’s Mortelle designed from Renzo Piano, taste their food paired with 4 of their top wines.
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  • 6 hours
  • Free Cancellation
From  
US$382.57
From  
US$382.57
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  • 6 hours
  • Free Cancellation

Day Trips

Private Vintage 500Fiat tour in Tuscany

Discover the Tuscan countryside behind the wheel of a classic Fiat 500 on a private six-hour tour. Starting from Florence, hit the open road with your guide.  Along the drive, you’ll visit three historic villages, stopping whenever you like.  Later, enjoy a traditional Tuscan lunch with wine tasting  at a 19th century villa.
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  • 6 hours
  • Free Cancellation
From  
US$228.40
From  
US$228.40
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  • 6 hours
  • Free Cancellation

Day Trips

Bike tour and wine tasting from San Gimignano

Discover the sights and flavors of Tuscany by bike on a private 6-hour tour. Set along gentle roads and trails, the countryside excursion is the perfect way to immerse yourself in the region’s world-famous landscape. Pedal your way to a traditional family farm and wine cellar. There you enjoy a filling meal paired with four different wines. Sample honey and homemade olive oil with bruschettas, cold cuts, and more.
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  • 6 hours
  • Free Cancellation
From  
US$154.17
From  
US$154.17
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  • 6 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Off Road 4WD wine tour

This personalized wine tour of Tuscany takes you off-road through the scenic landscapes outside Florence. Set off with your own private party into the Chianti wine region aboard a 4WD vehicle, and indulge in the ultimate wine-and-dine experience. You’ll visit two prominent wineries for seven wine tastings, food pairings, and lunch.
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  • 5 hours
  • Free Cancellation
From  
US$131.33
From  
US$131.33
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  • 5 hours
  • Free Cancellation

Wine Tasting & Winery Tours

Luxury Chianti Classico Experience

Visit Antinori nel Chianti Classico winery, taste 3 top wines. Later visit Villa Le Corti owned by Principe Corsini enjoy a great wine tasting of 4 wines and extra virgin olive oil. Dine in the private Villa of the Prince with three courses meal and grappa and extra virgin olive oil tasting. You will be escorted by an experienced Sommelier/wine expert driver-guide on luxury minivan Mercedes. 
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  • 6 hours
  • Free Cancellation
From  
US$365.44
From  
US$365.44
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  • 6 hours
  • Free Cancellation

Private Sightseeing Tours

Chianti Dreaming: Private Boutique Winery and Hilltop Village Tour

This 4-hour private tour allows you to visit Castellina, a medieval village in the Chianti region and do a wine tasting at a local winery. Get personalized attention and a flexible itinerary on this private tour for just you and your party of up to 8 people. Round-trip transportation from centrally located Florence accommodations included.
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  • 4 hours
  • Free Cancellation
From  
US$74.23
From  
US$74.23
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  • 4 hours
  • Free Cancellation

Private Sightseeing Tours

Make Your Own Wine with an italian Winemaker from Florence

Create your own ideal wine with this immersive tasting and blending workshop in Florence. In an ancient villa cellar, sample five different grapes straight from the barrel, then customize your very own blend with the help of a master winemaker. Enjoy a full case of your personal wine, shipped directly to your home with a custom label of your own design. A delicious Tuscan lunch with wine pairings is included to complete the tasting experience.
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  • 5 hours
  • Free Cancellation
From  
US$656.66
From  
US$656.66
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  • 5 hours
  • Free Cancellation


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