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19 Chianti Private Sightseeing Tours

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

Luxury Maremma wine tour

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  
$642
From  
$642
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  • 6 hours
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  • Free Cancellation

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

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  
$811
From  
$811
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  • 9 hours
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  • Free Cancellation

Wine tour with a Sommelier

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  
$265
From  
$265
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  • 5 hours
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  • Free Cancellation

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Private Truffle hunt in Tuscany from Florence

Private Truffle hunt in Tuscany from Florence

star-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  
$271
From  
$271
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  • 6 hours
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  • Free Cancellation

Brunello di Montalcino Wine Tour of 3 Wineries with Pairing Lunch

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  
$258
From  
$258
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  • 1 to 8 hours
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  • Free Cancellation

Montalcino and Montepulciano Wine Tour from Siena

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  
$462
From  
$462
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  • 6 hours
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  • Free Cancellation

Luxury Montalcino wine tour

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  
$620
From  
$620
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  • 6 hours
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  • Free Cancellation

Chianti Dreaming: Private Boutique Winery and Hilltop Village Tour

Chianti Dreaming: Private Boutique Winery and Hilltop Village Tour

star-5
This private tour allows you to visit Castellina, a medieval village in the Chianti region and do a wine tasting at a local winery. You can also upgrade your experience to include a stop in Greve, the birthplace of the navigator Giovanni da Verrazzano, and a second winery tasting. Get personalized attention and a flexible itinerary on this private tour for just you and your party of up to eight people.
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  • 4 hours
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  • Free Cancellation
From  
$236
From  
$236
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  • 4 hours
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  • Free Cancellation

Luxury Chianti Classico Experience

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  
$620
From  
$620
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  • 6 hours
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  • Free Cancellation

Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting

Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting

Grand tour of the Val D'Orcia allows you to discover the most beautiful Tuscan countryside with a Professional Tour Guide-SommelierThe small towns of Montalcino, Pienza and Montepulciano are the essence of this region, the dream of every curious traveler and lover of art, good food and great wines.Discover the splendid Renaissance town of Montepulciano, its splendid square, surrounded by magnificent palaces from the 1500s, its extraordinary underground medieval cellars, the elegant streets with small shops and artisan shops and wine bars. Be in love with Pienza, a UNESCO site, the charming village created by Pope Pius II, the extraordinary Renaissance cathedral, and the incredible view over the valley. Tasting of the delicious pecorino cheese.Visit the famous wine town of Montalcino and taste the celebrated Brunello di Montalcino wine in a winery. *** Trasportation is not included *you need of your own car for this tour. *I have my car I dont need to travel with you
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  • 8 hours
  • Free Cancellation
From  
$395
From  
$395
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  • 8 hours
  • Free Cancellation

Gastronomic Classic Car trip - 3 nights/days

Gastronomic Classic Car trip - 3 nights/days

We will collect you from your point of arrival & transport you to the hotel. Your classic car will be ready for you - we offer a choice of Fiat 500 & 850 (1960s), Alfa Spider (1980), Fiat 124 Spider (1978). All vehicles suit two adults - if bringing kids (1 - 2) you are restricted to the Fiats with 4 seats.The first hotel is located in the heart of the Chianti region and has stunning 360 degree views, a pool and plenty of space to relax. Your tour coordinator will get you situated in your room(s) and then will talk you through the road book and the next few days. Dinner will be booked at a local restaurant a short walk awayDays 2 and 3 you will drive yourselves following the provided road book to the next hotel. There are stops arranged for wine tours etc. The tour coord. will move bags & have all ready for your arrival. Dinner will also be organizedDay 4 you will be transported back to the starting point or we can arrange other transport to a different location - Extra cost
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  • 3 days
  • Free Cancellation
From  
$4,042
From  
$4,042
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  • 3 days
  • Free Cancellation

Montalcino and Pienza, The Dream land

Montalcino and Pienza, The Dream land

Experience the real Tuscan essence by visiting the Orcia Valley and its beautiful villages! Meet you guide in Montalcino, where the world-famous Brunello wine is produced! Wonder through the Medieval twisty streets and explore the Fortress, whose design became a model for all the Tuscan cities, the “Chiesa dei Senesi” and then head to the square housing the “Palazzo Comunale”; learn about the history of the village and its importance. Take a walk to the Cathedral for an amazing view on the valley surrounding Montalcino and stop for a glass of the celebrated Brunello before heading to Pienza! After a scenic drive through the vineyards, you will arrive in the heart of the Orcia! Pienza it’s a real and unexpected Renaissance jewel. Enjoy the artistic beauty by discovering the Cathedral as well as the Piccolomini Palace, once home to the Pope Pius II, among many other architectural jewels. Walk along the city walls for a breathtaking view and a tasting of the famous pecorino cheese.
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  • 6 hours
From  
$563
From  
$563
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  • 6 hours

Visit of the farm and tasting of pecorino and caprini

Visit of the farm and tasting of pecorino and caprini

A life experience in close contact with the rhythms of the shepherd and his animals to witness the magical transformation of milk into cheese.It is the possibility to spend an alternative day, a unique occasion to get to know and live as a pastor for a day!Has anyone ever tried to be a shepherd?Here is a truly unique experience where guests (young and old) have the opportunity to follow closely how a real farm is managed, from milking to cattle foraging, and then discovering how milk is transformed into cheese and ricotta ... and taste the company's products!
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  • 1 to 2 hours
  • Free Cancellation
From  
$34
From  
$34
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  • 1 to 2 hours
  • Free Cancellation

Livorno Shore Excursion from Livorno Port: Private Full day Tour Chianti

Livorno Shore Excursion from Livorno Port: Private Full day Tour Chianti

star-5
Traverse the Tuscan countryside and head right into the Chianti wine region during this private shore excursion from Livorno. Depart from the port in a private, air-conditioned vehicle and spend your day visiting vineyards for wine tastings, sampling Tuscan cuisine (at your own expense), and even visiting a medieval town. An English-speaking driver-guide, free Wi-Fi aboard your vehicle, and round-trip port transfers are included.
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  • 9 hours
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  • Free Cancellation
From  
$811
From  
$811
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  • 9 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Bike tour and wine tasting from Florence

Bike tour and wine tasting from Florence

Discover the Tuscan countryside and cuisine on a private 6-hour bike tour from Florence. After transfer from your hotel, hop on a provided bicycle and follow your guide through the world-famous Tuscan landscape. The scenic journey takes you to a family farm where you enjoy a gourmet lunch prepared using local ingredients. The culinary experience continues with wine and olive oil tastings, before a leisurely ride back to the starting point.
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  • 6 hours
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  • Free Cancellation
From  
$271
From  
$271
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  • 6 hours
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  • Free Cancellation

CHIANTI CLASSICO ORGANIC WINE TOUR

CHIANTI CLASSICO ORGANIC WINE TOUR

star-5
Oenophiles will appreciate this tour through Tuscany, which is known for its outstanding Chianti wine. Visit a working vineyard to learn about and sample Chianti Classico, Chianti Riserva and Super Tuscan wines. Take a break to explore a nearby Medieval village, then visit a second farmhouse-style winery to sample more wines and local olive oils.
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  • 7 to 8 hours
  • Free Cancellation
From  
$485
From  
$485
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  • 7 to 8 hours
  • Free Cancellation

Chianti wine tour

Chianti wine tour

The ultimate wine tour take you in the best area for wine production in Tuscany.We are certified sommeliers and we offer an amazing learning and discovery experience.
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  • 6 hours
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  • Free Cancellation
From  
$395
From  
$395
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  • 6 hours
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  • Free Cancellation

Pasta and Wine tasting experience in Tuscany

Pasta and Wine tasting experience in Tuscany

Pasta and wine: the things you think about when it comes to Tuscany. What’s behind? Do you know how wheat becomes pasta and grapes turn into wine? Now you have the chance to learn about it. First  you will visit a pasta factory in Chianti, owned for more than 100 years by the same family then a beautiful winery, visiting the celler and enjoy a great lunch paired with top wine selection of the Cantina!
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  • 5 hours
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  • Free Cancellation
From  
$380
From  
$380
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  • 5 hours
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  • Free Cancellation

Grape stomping in Tuscan farmhouse from Florence

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  
$282
From  
$282
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation


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