Arezzo
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Private tour Wine and cheese a perfect combinations val 'Orcia
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.
4.5(6)
8 Hours - 9 Hours
Arezzo
- Free cancellation
- Private tour
- Likely to sell out
From
$547
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Viator
Typical Tuscan family dinner in a Villa near Cortona
you will meet our family! We have lived in Tuscany all our lives! we will reveal the secrets of our cuisine to you and you will be able to see while we cook for you! it will be an unforgettable experience, we will taste a lot of wine and also our extra virgin olive oil!
3.7(3)
3h 30m
Arezzo
- Free cancellation
- Private tour
From
$81
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Viator
PRIVATE TOUR: Sweet Hills of Chianti & Siena + Lunch & 2 Tastings
A full day trip into the landscape of the rolling Chianti hills, cypress avenues, medieval villages and tasting of the best wines of our region. In the morning, meet the driver at your hotel or another chosen location. We'll cross the rolling Tuscan hills, among olive groves, cypresses & vineyards. •Visit the magnificent city of Siena and the historic center. Siena is famous for its stunning architecture and beautiful main square: Piazza del Campo. Siena has a historic center that has been declared a world heritage site by UNESCO. Siena is also known for its legendary Palio horse race which takes place twice a year and attracts hundreds of spectators. •Next move to a real Tuscan farm, to understand the secrets of wine production and enjoy a lunch with homemade pasta and 6 wine tastings. •After lunch, visit the wonderful Medieval Castle of Monteriggioni. •On the way back you will have a second wine tasting in a Chianti winery tasting the King of the wines: The Chianti Black rooster.
8 Hours
Arezzo
- Free cancellation
- Private tour
From
$297
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Viator
Tasting with Private Walk in a Cellar in Tuscany
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
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$30
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Viator
PRIVATE TOUR: Visit Siena and Chianti with Lunch & Wine Tasting Experience
Spend a day exploring the iconic Chianti hills, a picture-perfect landscape of cypress-lined avenues, rolling vineyards, sunflower fields, and medieval villages. This tour combines history, breathtaking views, and authentic Tuscan cuisine for an unforgettable experience. Highlights: • Explore Siena: Begin with a visit to Siena, renowned for its stunning UNESCO World Heritage architecture and the historic Piazza del Campo. Enjoy free time to discover this medieval gem at your own pace. • Lunch at a Tuscan Farm: Travel to a traditional Tuscan farmhouse and indulge in a homemade lunch featuring fresh pasta, cold cuts, Pecorino cheese, and 5 wine tastings, including Chianti wines. Learn about local winemaking traditions while savoring the flavors of Tuscany. • Return by approximately 4:00 PM. This experience is perfect for travelers who want to immerse themselves in the beauty, history, and flavors of Tuscany!
8 Hours
Arezzo
- Free cancellation
- Private tour
From
$297
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Viator
PIENZA Countryside E-Bike and Exclusive Mill Journey
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.
4 Hours - 5 Hours
Arezzo
- Free cancellation
- Private tour
From
$446
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Viator
Cortona Ultimate Private E Bike and Winery Experience
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.
5 Hours - 6 Hours
Arezzo
- Private tour
- New
From
$820
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Viator
Private Luxury Photo and Video Shoot in Val d'Orcia
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
2 Hours - 4 Hours
Arezzo
- Free cancellation
- Private tour
- New
From
$593
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Viator
Cortona Private Pick&Taste - Valley, Castle With Lunch and Wine
Hosted personally by a local curator specialized in private experiences. Not a tour, but a privately curated day through the hidden treasures of Cortona Valley. Access medieval castle, historic abbey, and secret estates normally closed to visitors, all at a relaxed pace. Along the way, you’ll pick and collect hidden local treasures, from artisanal products to olives and specialty ingredients, later enjoyed with a refined Tuscan wine pairing. Enjoy a private lunch and tasting with a curated itinerary, ensuring no overlapping groups and a premium pickup experience. Every moment is designed to delight your senses and create memories that last. Fully private, each step is carefully crafted to immerse your group in Tuscany’s culture, traditions, and seasonal delights — far from the crowds and tailored entirely to your experience.
5 Hours - 6 Hours
Arezzo
- Free cancellation
- Private tour
- New
From
$710
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Viator
Explore Pienza From Ideal Renaissance City to Tuscan Views
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.
2 Hours
Arezzo
- Private tour
- New
From
$238
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Viator
7-Day Exclusive Escape to Cortona Italy
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.
7 Days
Arezzo
- Private tour
- New
From
$2,800
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Viator
Wine Tasting: a SYRAH that makes you fall in love
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.
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$36
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Viator
Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings
Follow the trail of the film "Under the tuscan sun". We will take you to the rolling Tuscan landscape, among vineyards, art and sunflowers. We will visit the countryside and the city of Cortona, "the secret underground cellars" of Montepulciano. You will taste the best wines of our region and have a typical Tuscan lunch. Itineraty: • We will explore southern Tuscany and visit the medieval city of Cortona and the Monastery of San Francesco called "Le Celle" • We will stop to take photos of the landscape along the road featured in the film "Under the Tuscan Sun" • Later we will visit the "Underground Wonders" of Montepulciano (The Historic Cellars of the city) where you will find gigantic oak barrels, in which the famous Vino Nobile di Montepulciano DOCG "rests". • In Montepulciano we will have a delicious lunch and two wine tastings in two different cellars. The return is scheduled for 5pm
8 Hours
Arezzo
- Free cancellation
- Private tour
From
$309
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Viator
2 Hours Free Arezzo tour - Smartphone free
Arezzo Digital Detox is to rediscover the beauty of living an experience while remaining 100 percent present, without the distractions caused by unnecessary notifications and messages. An itinerary of about two hours, at the beginning of which each participant will be provided with a kit complete with accessories and documents to be used during the journey. The kit will include, among other things, a map of the route, a notebook with all the necessary information, trivia and tips on how to best approach your walk among the city streets Please note, this activity does not include a tour leader or an accompanied service.
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$29
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Viator
Chianti Classico Black Rooster Private Wine Tour from Cortona
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.
8 Hours - 9 Hours
Arezzo
- Free cancellation
- Private tour
- New
From
$559
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Viator
Arezzo: Private tour with the Legend of the True Cross
Arezzo is famous because Giorgio Vasari was born here, the disciple of Michelangelo, who designed the famous Uffizi and the Vasari Corridor in Florence on behalf of Grand Duke Cosimo I De' Medici. Our tour's principal stops are as follows: The city's center square, Piazza Grande, is uniquely typical with its porticoes dating from the sixteenth century. Piazza del Duomo: this stunning medieval structure, dominating the plaza, houses priceless artwork by Donatello and Piero della Francesca. Arezzo's ancient lanes and streets, where the ambiance of the old goldsmith shops is still palpable. The most well-known painting by 15th-century painter Piero della Francesca is located in the Basilica of San Francesco, Cappella Bacci. Based on the advice of Dominican priest Jacopo da Voragine, these frescoes tell the story of the True Cross! How could anyone possibly miss a tour this thorough? Now let's move!
2 Hours
Arezzo
- Free cancellation
- Private tour
- New
From
$237
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Viator
Tuscany Multi Day Bike Tour History Wine and Local Flavors
Book for an unforgettable cycling experience in Tuscany — carefully designed routes, top-quality equipment, and private tastings in authentic local settings.
7 Days
Arezzo
- Private tour
From
$5,000
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Viator
Private Valdorcia Ebike Tour with Tuscan Pecorino Cheese Tasting
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.
4 Hours - 6 Hours
Arezzo
- Free cancellation
- Private tour
From
$666
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Viator
Kid Friendly Cortona Private Guided Tour for Families
Discover the charm of Cortona on our kid-friendly tour designed to engage and entertain the entire family! This enchanting adventure begins with a visit to the Basilica of Santa Margherita to admire the stunning architecture and frescoes. Next, we head to the Belvedere, offering breathtaking views of the surrounding Tuscan landscape that will captivate both young and old. It's the perfect spot for family photos and a moment of awe. Our journey continues to Piazza della Repubblica, the vibrant heart of Cortona's old town. We will then explore the charming old town, wandering through its picturesque streets and uncovering hidden gems along the way. The tour includes an external view of the magnificent Cathedral of Santa Maria Assunta, an architectural marvel that adds to the town's rich historical tapestry. Book an unforgettable 2-hour family adventure in Cortona, where history, culture, and fun combine to create lasting memories for everyone!
2 Hours
Arezzo
- Private tour
From
$256
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Viator
Kid-Friendly Arezzo Private Guided Tour for Families
Explore the enchanting city of Arezzo on our private kid-friendly tour designed to captivate the imagination of the whole family! Our adventure begins at the picturesque Piazza Grande, the heart of Arezzo, where you will be amazed by the medieval architecture and the lively atmosphere. Next, we will marvel at the imposing Medici Fortress and the Duomo from the outside. One of the highlights of our tour is the entrance to the Archaeological Museum of Gaius Mecenas and the adjacent Roman Amphitheater. Here, kids will have the chance to uncover the mysteries of ancient Rome through interactive exhibits. Additionally, fans of the beloved movie "La Vita è Bella" will delight in spotting the iconic filming locations throughout the city, adding a touch of cinematic magic to our journey. Join us for an unforgettable 2.5-hour adventure in Arezzo, where history, culture, and fun come together to create lasting memories for the entire family!
2h 30m
Arezzo
- Private tour
From
$271
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Viator
Arezzo Interactive City Tour
Discover Arezzo your way with Ciceru’s self-guided walking tour—audio and text in 7 languages, right on your phone. No app, no hassle—just press play and explore! Walking through the streets of Arezzo is like stepping back in time. Be enchanted by the frescoes of Piero della Francesca, the grandeur and splendour of the Duomo and the wonder of Piazza Grande. Arezzo is the ideal destination for a short trip between nature, art and good food!
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$8
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