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29 results
Best Seller
Spend a full day visiting the family-run wineries and olive oil producers that surround Cortona—hidden gems that are tricky to find without a local connection. A guide drives you and your group between estates where you taste wines and extra-virgin olive oil, tour vineyards and aging rooms, and speak directly with the people who make them.
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5.0
(50)
Wine and olive oil tastings with the locals
8 hours
Free Cancellation
from
$252
Esplora il mondo del vino toscano in una tenuta vinicola sulle colline fuori Arezzo con un tour privato. Visita i vigneti e le sale per le botti di Villa Fabbriche per conoscere la storia e la produzione dei loro vini rossi e bianchi. Poi rilassati e degusta un pranzo a base di affettati locali, formaggi, bruschette, olio d'oliva, verdure di stagione e altre specialità abbinate a una selezione di vini della tenuta.
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(43)
Cellar Tour & Wine Tasting
3 hours
Free Cancellation
from
$60
Tuscany produces one of Italy’s flagship wines: Brunello di Montalcino. Exploring the countryside where these wines are produced, however, means navigating confusing rural roads and searching for remote wineries. With this wine tour, leave the hassle of driving to the experts and instead enjoy a stress-free day of wine tasting and sightseeing. Visit two winereis and a cellar.
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4.6
(23)
Brunello and Montepulciano Wine Tour from Cortona
6 to 8 hours
Free Cancellation
from
$599
Price varies by group size
Tasting with the senses: a sensory experience that will accompany enthusiasts to the cellar to learn about how our Syrah is born and to savor its peculiarities. An all-round gustatory embrace that leads us to welcome, by reservation, small groups of enthusiasts, from two up to a maximum of eight people.
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Wine Tasting: a SYRAH that makes you fall in love
2 hours
Free Cancellation
from
$36
Tuscany is one of the most beautiful areas in Italy, with lots of spots to take magical photographs. I will create magical memories through the photos for you to keep forever. Exploring the famous and hidden gems together will be great!
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201
Operator reviews
Tuscany Private Photoshoot Experience
2 hours
Free Cancellation
from
$925
Per group
Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Rome. Come and savor the very best of the Tuscan countryside—its flavors, stories, and breathtaking views. Exclusive & Intimate: Small-group experiences (max 7 per guide) ensure personalized attention and genuine local interactions. Unforgettable eBike Rides: Explore ancient paths, scenic vineyards, and breathtaking landscapes on high-performance pedal-assist bikes. Culinary Immersion: Savor authentic Tuscan flavors through unique dining experiences—from a hillside cheese house picnic to a hands-on cooking class and intimate restaurant dinners. Cultural Insights: Engage with local experts who unveil the hidden stories and history of this iconic destination. Book now for a once-in-a-lifetime adventure through Tuscany—a journey that delights your senses and nourishes your soul! Contact Us: For more detailed information or to receive a discount code for your booking, please contact us before booking.
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Operator reviews
Tuscany Multi day eBike tour Wine and Pasta
4 days
Free Cancellation
from
$2,954
See Tuscany’s loveliest scenery, and discover the history of one of Italy’s most revered wines, on this private, half-day tour. Following pickup from your area hotel, head off the tourist trail to a local, family-owned winery. Taste Brunello di Montalcino—a 100% Sangiovese wine that’s one of Italy’s best—as well as other wines and nibbles. You’ll also tour the idyllic Val d’Orcia, from ancient hill towns to historic monasteries.
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5.0
(94)
Brunello Wine Tour and Val D'Orcia Landscape
4 hours
Free Cancellation
from
$265
We offer an excellent tasting of typical products of the area that, usually, one would expect to find in the boundless countryside, the peculiarity of the experience we offer is the location in the historic center, in Piazza Grande, in the main square of Arezzo. The proposed activity can be implemented in two ways, with the basic tasting (€25), or with the tasting upgrade, which includes our truffle-based products and more! (€40): -1 GLASS OF CHIANTI COLLI ARETINI DOCG WINE -1 GLASS OF IGT ROSÉ WINE -1 GLASS OF CHIANTI RISERVA DOCG WINE -BRUSCHETTA WITH BORGUNTO EVO OIL -VEGETARIAN BRUSCHETTA WITH TRUFFLE MAYONNAISE -TRUFFLE BUTTER BRUSCHETTA -TRUFFLE POPCORN -TOMATO JELLY -RIBOLLATO -TRUFFLE CHEESE AND HONEY -PEACHES IN SYRUP
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Chianti tasting Arezzo city center Wine & Oil
1 hour 30 minutes
Free Cancellation
from
$30
Discover Cortona on a private, fully curated luxury e-bike journey blending breathtaking Tuscan landscapes, culture,and authentic local experiences.Ride premium e-bikes along serene, scenic routes with a professional local expert who brings the region to life with stories, history, and insider knowledge far from crowded paths.Pause to admire charming corners and hidden views, feeling the rhythm of the rolling hills and medieval streets. The journey culminates at a refined, private winery where the owner welcomes you for a curated Tuscan lunch with no overlapping. Savor seasonal appetizers highlighting the finest local products, a thoughtfully prepared first course, dessert or gelato and coffee,paired with at least three glasses of Syrah from different vintages to reveal depth and character.Designed for couples, families, and discerning travelers, this is a seamless, immersive, and unforgettable way to experience Cortona—where every detail is crafted for comfort, privacy, and discovery.
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Operator reviews
Cortona Private Hero Experience Luxury E-Bike Lunch and Wine Tour
5 to 6 hours
from
$438
Pick up e Drop off from Pienza .Join us for a hands-on cooking class where you’ll master the techniques of preparing authentic Tuscan pasta, all while enjoying a delightful meal paired with our exquisite wines, including Brunello di Montalcino.You’ll have the chance to explore our historic cellar and indulge in a feast featuring a selection of mixed Tuscan appetizers, homemade pasta, and dessert, all accompanied by three organic wines, including Brunello and Rosso di Montalcino.As part of the tasting experience, you’ll even have the opportunity to sample wine straight from the wooden barrel!Feel free to capture the moments and share your culinary adventure on your social media!
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From Pienza Pasta Class with Brunello Wine Tasting and Lunch
2 hours 30 minutes
Free Cancellation
from
$311
Likely to Sell Out
Swap the cobbled streets of Cortona for its surrounding countryside on this small-group e-bike tour—and cover plenty of ground with ease. Follow the winding Tuscan roads through the Val di Chiana with views of vineyards and cypress-lined hills. A local guide leads the way and adjusts the route based on the group, stopping at a boutique winery where an optional wine tasting and lunch are available.
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4.9
(42)
Cortona - eBike tour and wine tasting in the Val di Chiana [+40€]
5 to 6 hours
Free Cancellation
from
$225
What makes this experience truly special is its warm and inclusive atmosphere—ideal for families with children, couples, and groups of friends looking for a break from the city and the usual tourist hotspots. The cooking class is led by a patient and passionate chef, making it fun and accessible for everyone. You’ll use only fresh, high-quality ingredients from small local producers, ensuring an authentic and flavorful taste of Tuscany. Set in the exclusive Agriturismo Armaiolo, the location feels like stepping into another era—peaceful, scenic, and far from the crowds.
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Hands-on Cooking Class, Truffle Lunch & Wine in Siena, Tuscany
3 hours 30 minutes
Free Cancellation
from
$300
Explore the exquisite wines of Tuscany on the Brunello di Montalcino Wine Tour from Pienza. This half-day adventure takes you to the renowned Wine Resort Colsereno, where you’ll indulge in wine tastings and a delicious lunch featuring local flavors. Enjoy a comfortable ride in an air-conditioned vehicle while learning about the rich history and craftsmanship of Brunello wines from expert guides. Perfect for wine lovers, this small group tour ensures a personalized experience, accommodating dietary preferences.
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Brunello di Montalcino Wine Tour from Pienza with Lunch
4 hours
Free Cancellation
from
$167
This isn’t your average wine tour—it’s a relaxed, hyper-local adventure around one of Umbria’s hidden gems: Lake Trasimeno. What sets us apart is the mix of boutique wineries, charming lakeside villages, and those off-the-beaten-path moments that feel so authentically Italian. And the best part? You’ll be hosted by Monia—your local culture ambassador, storyteller, and all-around Umbria insider. She’ll connect you with the land, the people, and the wine in a way that’s personal, meaningful, and seriously fun. No big buses, no boring scripts—just real connections, great wine, and unforgettable views.
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5.0
(7)
Umbria like a local: Private Wine Tasting & Dining Experience
9 hours
Free Cancellation
from
$779
Enjoy a wine tasting experience in an ancient villa located in Valdichiana in the heart of Tuscany. Wander the vineyard and admire the amazing Tuscan landscape. Learn about the history of the location and get an explanation about the methods and techniques of wine production. During the experience, taste three Tuscan wines as a professional sommelier explains the particularities of the wines.
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Arezzo: Wine Tasting Experience in Valdichiana area
2 hours
Free Cancellation
from
$48
Book for an unforgettable cycling experience in Tuscany — carefully designed routes, top-quality equipment, and private tastings in authentic local settings.
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Tuscany Multi Day Bike Tour History Wine and Local Flavors
7 days
from
$5,000
Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.
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(57)
Private Tour: Montalcino Wine Tasting Experience
8 hours
Free Cancellation
from
$420
Price varies by group size
Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a full day dedicated to wine and cheese, exploring the heart of Tuscany. Drive through the Val d'Orcia, a UNESCO World Heritage Site, and savor some of the region’s finest red wines, including Vino Nobile di Montepulciano and Brunello di Montalcino. Stroll through the medieval squares of Pienza and sample authentic Tuscan cheeses at a historic estate, featuring one of the most breathtaking terraces overlooking the Orcia Valley.
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4.5
(6)
Private tour Wine and cheese a perfect combinations val 'Orcia
8 to 9 hours
Free Cancellation
from
$552
Price varies by group size
Tuscany is famed for its scenery and gastronomy, but navigating this rustic region isn’t easy—especially for first-time visitors. Enjoy a deluxe introduction to the rolling Tuscan landscape during this full-day tour of Cortona and Montepulciano. A heart Tuscan lunch is included, plus a guided tour of a historic wine cellar and five exclusive wine tastings.
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39
Operator reviews
Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings
8 hours
Free Cancellation
from
$312
Price varies by group size
This exclusive private wine tour takes you from Cortona to the heart of the Chianti Classico Black Rooster, an iconic wine area rarely reached from this part of Tuscany. Travel in comfort with a local professional driver and enjoy a personalized journey through one of Tuscany’s most celebrated wine landscapes. The experience includes visits to three carefully selected Chianti Classico DOCG wineries, where you will enjoy guided cellar tours and premium wine tastings. Each winery offers a different perspective on the Black Rooster tradition, allowing you to discover the diversity, history, and craftsmanship behind authentic Chianti Classico wines. A traditional Tuscan lunch is included, perfectly paired with local wines and seasonal products, for a complete and immersive Chianti experience. Designed for travelers seeking authenticity, privacy, and high-quality wine experiences, this tour combines culture, scenery, and exceptional flavors in a relaxed and exclusive setting.
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Operator reviews
Chianti Classico Black Rooster Private Wine Tour from Cortona
8 to 9 hours
Free Cancellation
from
$564
Price varies by group size
Likely to Sell Out
Explore Tuscany and savor the wines of the region on this private all-day tour. Visit the medieval cities of Montepulciano, Pienza, and Montalcino and discover historic cellars. Enjoy wine tastings with a light lunch, then head to Pienza, where Pecorino cheese is made. Stop in Montalcino to see the castle and visit a winery where you’ll taste Brunello di Montalcino, one of Italy's most prestigious wines.
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(6)
PRIVATE TOUR: Savor Exquisite Wines, Brunello & Nobile Wine Tour
8 hours
Free Cancellation
from
$300
Price varies by group size
A private professional photo and video experience in the Val d’Orcia, designed for elegant and authentic visual memories. I personally guide you through the most iconic locations starting from Pienza, selecting the best light and cinematic angles to create natural, high-quality photos and videos. What’s included: – 30 professionally edited photos – 1 cinematic video trailer (approx. 2 minutes) with professional editing and color grading – Video delivered in both 16:9 and 9:16 formats – Professional equipment and aerial drone footage (where permitted) – Digital delivery via email within 3 days
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Private Luxury Photo and Video Shoot in Val d'Orcia
2 to 4 hours
Free Cancellation
from
$599
Per group
If we talk about Tuscany, we cannot ignore the culture linked to tradition and history: the proposed activity is one of a kind, and interesting, since it allows access to a symbolic place of the valley that would otherwise not be possible to visit. Podere degli Olmi is the only original Leopoldina house that can be visited, and since it is private, access is only possible through this experience. The guide will be the descendant of one of the oldest noble families, who will tell you every detail of the Valdichiana and its traditions. You will take a leap back a few centuries, and it will be interesting to be in the presence of objects and walls full of history and years. The visit will end with a tasting of typical products linked to the territory, the history and cultivation of which will be illustrated to you, so that you can spend an evening learning about the secrets and nature of the territory that hosts you: the Valdichiana.
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Private visit to the House of Grand Duke Leopold of Tuscany with invitation
2 hours 30 minutes
Free Cancellation
from
$48
Price varies by group size
It's one thing to eat pizza in Italy, but it's another experience entirely to learn how to make it from scratch. Join this small-group cooking class in the heart of Arezzo and discover the authentic way to make pizza with step-by-step instruction from a local pizzaiolo (traditional pizza chef). At the end, dine on your creation, sip a glass of wine, and enjoy an experience you can't achieve with a restaurant reservation alone.
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Operator reviews
Arezzo Hands-On Pizza Class: From Dough to Dessert and Wine
3 hours
Free Cancellation
from
$143
Price varies by group size
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