Top Arezzo Holidays

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.

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.

Head to an authentic family-run vineyard and winery near the walled town of Castiglion Fiorentino to discover Tuscan wine-making traditions on this private tour. Explore the vineyard (weather permitting), the cellars, and the Vin Santo production area as you hear about the techniques the family has used for generations. Wrap up with a tasting of cheese, salami, extra virgin olive oil, and six different wines.

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.

Embark on a private, guided journey through the picturesque vineyards and historic cellars of Montepulciano, the home of the celebrated Vino Nobile di Montepulciano. This exclusive tour offers an immersive experience that captures the essence of Tuscan winemaking tradition. What to Expect Guided Visits to three renowned Wine Estates: Explore estates with centuries of winemaking expertise. Learn about the intricate process of crafting Vino Nobile di Montepulciano from passionate experts. Exclusive Wine Tastings: Savor a curated selection of exquisite wines at each estate. Lunch at the Second Estate: Indulge in a traditional Tuscan meal paired with exceptional wines. This intimate experience blends Tuscan culture, history, and gastronomy into a memorable day amidst the stunning countryside of Montepulciano. Whether you're a wine enthusiast or simply looking to enjoy a luxurious day in Tuscany, this tour is the perfect choice.

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.

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.

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.

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.

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

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.

Explore the exquisite wines of Tuscany with the Brunello di Montalcino Wine Tour from Cortona. This half-day adventure takes you to the renowned Wine Resort Colsereno, where you’ll enjoy wine tastings and a delicious lunch featuring local flavors. Relax on 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 and can accommodate dietary preferences.

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.

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.

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.

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.

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.

Book for an unforgettable cycling experience in Tuscany — carefully designed routes, top-quality equipment, and private tastings in authentic local settings.

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.

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.

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!

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.

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.