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64 results
This isn’t just a vacation — it’s an immersive Tuscan journey where you’ll: Taste Italian cuisine and recipes passed down through generations. Wander cobblestone streets in Cortona and beyond Indulge gelato daily. Share sunsets over rolling hills with friends and family.
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7-Day Exclusive Escape to Cortona Italy
7 days
from
USD 2,800
In the cellar, in Mugliano, we offer the opportunity to taste our organic products combined with cutting boards made with local products in the different locations present, from the "Garden" to the "Barricaia", to the "Wine Rooms". The wine cellar and the garden atmosphere will guarantee the wine enthusiast a special experience.
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Private Tasting of Organic Wines in the Cellar in Mugliano
2 hours
Free Cancellation
4.7
(11)
from
USD 35
Optimize your logistics and make the most of your time with this private transfer from Florence to Assisi that includes stops to visit the Tuscan hill towns of Montepulciano and Cortona. Enjoy the ease of pickup at your Florence hotel and explore towns worry-free while your driver stays with the vehicle and your luggage. Sightsee, shop, and dine at your own pace, then end your day with seamless drop-off directly at your Assisi hotel.
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PRIVATE TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona
8 hours
Free Cancellation
5.0
(40 Operators)
from
USD 292
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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Chianti Classico Black Rooster Private Wine Tour from Cortona
8 to 9 hours
Free Cancellation
5.0
(43 Operators)
from
USD 548
Price varies by group size
Ride through the rolling hills of Pienza’s countryside on a private e-bike experience, discovering charming landscapes and historic villages. After the ride, step by step, visit a working mill where your guide will show the journey from wheat to fresh pasta, sharing local stories, traditions, and insights into Tuscan culture, wine, gastronomy, and the region’s vineyards. Glide through vineyards and golden fields in the heart of UNESCO-listed Val d’Orcia, near Montalcino, enjoying cinematic views, iconic cypress-lined roads, and hidden gems beyond usual sights. With TREK e-bikes and carefully chosen routes, the journey unfolds at a relaxed pace, letting you explore far from crowds. The tour concludes with a light Tuscan lunch in a special setting beside a castle, offering a final gastronomic moment highlighting the region’s culture, flavors, beauty, and local craftsmanship — an immersive Tuscan journey for travelers seeking authenticity, refinement, and true Tuscan elegance.
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PIENZA Countryside E-Bike and Exclusive Mill Journey
4 to 5 hours
Free Cancellation
5.0
(31 Operators)
from
USD 437
Walking through the medieval streets of Arezzo is a unique experience. Tradition, history and beautiful landscapes to photograph. Arezzo offers all this and much more. The tour aims to show the truest Tuscany, far from the classic tourist routes. Booking a day in Arezzo allows you to relax in one of the most beautiful medieval cities in Tuscany.
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Private and Guided Walking Tour of Arezzo City of Gold
2 to 3 hours
Free Cancellation
5.0
(1)
from
USD 257
Per group
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
USD 35
Get to know an Italian family by dining with them in their home. Take the stress out of finding a restaurant by booking this private dinner for an intimate experience of Italian cuisine and culture. You and your group will enjoy a delicious three-course meal paired with local wine. Sample delicacies like tiramisu and pasta dishes made using fresh ingredients from their garden.
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Typical Tuscan family dinner in a Villa near Cortona
3 hours 30 minutes
Free Cancellation
3.7
(3)
from
USD 79
This tour of Pienza stands out by combining clear Renaissance urban design with authentic local culture and scenic landscapes in a compact and accessible format. The route covers key spaces, beginning at Porta al Prato, continuing along Corso Rossellino, and arriving at Piazza Pio II, where architecture, history, and civic identity come together. It then reveals panoramic views from Via dell'Amore, explores quieter backstreets such as Via del Bacio, and incorporates a culinary stop that highlights regional traditions. Throughout the experience, the tour connects built form with natural surroundings, balances major landmarks with intimate spaces, and allows a deeper understanding of how planning, culture, and landscape interact within a unified setting.
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Explore Pienza From Ideal Renaissance City to Tuscan Views
2 hours
from
USD 233
Price varies by group size
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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Tuscany Multi day eBike tour Wine and Pasta
4 days
Free Cancellation
5.0
(188 Operators)
from
USD 2,869
Likely to Sell Out
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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Private tour Wine and cheese a perfect combinations val 'Orcia
8 to 9 hours
Free Cancellation
4.5
(6)
from
USD 536
Price varies by group size
A true paradise nestled in the Tuscan hills where once stood a temple dedicated to the mythological hero Hercules. We are in Val di Chiana, a production area of Chianti, a land of excellence that offers scenic wonders, where the winemaking tradition is expressed at the highest levels. We produce wines with a Tuscan soul, thanks to the passion for wine and the love for our territory that accompany the entire production process. We offer exclusive packages to visit our estate with expert guides and live a unique experience. The strategic position of Camperchi, just 5 minutes from the A1 Monte San Savino motorway exit, offers the opportunity to discover the wonders that Tuscany and Umbria offer
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Tasting with Private Walk in a Cellar in Tuscany
2 hours
Free Cancellation
from
USD 29
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
USD 5,000
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
USD 582
Per group
Discover Cortona through an exclusive private journey for travelers seeking the highest level of authenticity and comfort. Ride premium e-bikes along quiet panoramic routes guided by a local expert who shares stories, culture, and hidden perspectives of Tuscany.Enjoy privileged access to a family-owned olive oil estate dating back to the 1800s, where a private visit reveals traditional production methods, historic tools, and centuries of heritage rarely experienced by visitors. Conclude the day with a refined winery experience with a curated lunch and exceptional wines in an intimate setting, with no overlapping groups.As a final gesture, guests receive a personally selected bottle of estate olive oil — a lasting memory of Tuscany. Designed as a fully private experience, every detail is tailored to create rare access, genuine connection, and unforgettable moments.Ideal for travelers who prefer meaningful experiences over crowded tours and value time, privacy, and true Tuscan elegance.
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Cortona Ultimate Private E Bike and Winery Experience
5 to 6 hours
5.0
(31 Operators)
from
USD 805
Explore the enchanting landscapes of Pienza on our e-bike tour, featuring visits to iconic attractions such as the picturesque streets of Pienza and the rolling hills of Val d'Orcia. What makes this tour truly special is the immersive cultural experience it offers, including a cheese-tasting and lunch at one of the area's best cheese farms. Led by knowledgeable local guides, you’ll gain insider insights into the region’s rich history and traditions. Perfect for adventure seekers and families with children, this tour combines stunning scenery with a taste of Tuscany’s renowned culinary heritage, ensuring a memorable and enriching experience for all participants. Enjoy the perfect blend of adventure, culture, and gastronomy in the heart of Tuscany.
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Private Valdorcia Ebike Tour with Tuscan Pecorino Cheese Tasting
4 to 6 hours
Free Cancellation
5.0
(86 Operators)
from
USD 653
Price varies by group size
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