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64 results
Likely to Sell Out
Put a professional touch on your Tuscany vacation photos, and book a day-long photo tour with an award-winning photographer at your side. Created and led by the talented Marco Bulgarelli, the tour takes you to impressive vantage points around Val d'Orcia and the Siena province where gorgeous shots are guaranteed every time.
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Private Tuscany Photo Tours
8 hours
Free Cancellation
4.9
(18)
from
$354
Price varies by group size
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
$80
Explore the beautiful landscape of Val d'Orcia on this guided bike tour. Travel across easy rolling hills and admire the scenery of the Tuscan countryside before arriving at a thermal bath in Bagno Vignoni. Begin in Pienza and cross the green pastures where many cheese factories produce Pecorino. Then, coast downhill to the spa town of Bagno Vignoni, a village whose ancient stone buildings cluster around a pool of warm thermal waters. Choose to return to Pienza by van or bike.
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Bike Ride immersion val d'Orcia
3 to 6 hours
Free Cancellation
5.0
(5)
from
$142
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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PRIVATE TOUR: Savor Exquisite Wines, Brunello & Nobile Wine Tour
8 hours
Free Cancellation
4.8
(6)
from
$295
Price varies by group size
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
Perfect for families, couples, and solo travelers who want to enjoy the peace of the Tuscan countryside, where fresh air replace the city's summer heat. Here what makes it special: Real Truffle Hunt: a 50-minute walk through the woods, learning the secrets on how to find fresh truffles in their natural environment. Hands-On Cooking Class: Make fresh pasta & classic Italian tiramisu from scratch, using top-quality ingredients. Traditional recipes are revisited with the unique flavor of truffle. Gourmet 4-Course Lunch: Enjoy a truffle-based meal featuring what you’ve prepared, with one bottle of local wine for every two guests, served in a charming rural setting. Stunning Location: Set at Tenuta Armaiolo, a historic estate surrounded by wild nature, olive groves, and rolling hills. The atmosphere is timeless and peaceful. Social & Unforgettable: A chance to relax, connect, and experience something truly unique—perfect for meeting people, learning, and enjoying authentic Tuscany.
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Truffle Hunting, Cooking Class & Gourmet Lunch in Siena, Tuscany
4 hours 30 minutes
Free Cancellation
5.0
(4)
from
$402
Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit historic landmarks, lush vineyards, and stunning viewpoints, all while enjoying the ease and fun of electric biking. Afterward, immerse yourself in the rich culinary traditions of the region with a hands-on cooking class led by a local chef. Learn how to make the most famous shape of pasta in the area: PICI! Perfect for adventure seekers, food enthusiasts, and families, this tour offers a unique blend of outdoor adventure and authentic cultural experiences that will leave you with unforgettable memories of Tuscany.
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Around Lucignano Private ebike tour and Cooking Class
4 to 6 hours
Free Cancellation
5.0
(2)
from
$638
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
$589
Per group
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
$555
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
$30
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
$35
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
5.0
(7 Operators)
from
$176
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
$661
Price varies by group size
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
$543
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
$2,905
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
$815
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