Top Umbria Holidays

Escape the crowds in Assisi and head to the scenic hillsides for a wine tasting overlooking the Umbria Valley. Connect with a local winemaking family and take a stroll through the estate’s vineyards and olive trees to enjoy the views. Then relax over an al fresco wine tasting featuring four different organic wines served with a selection of bruschette, extra-virgin olive oil, local cheeses and cold cuts.

While on vacation, it’s sometimes nice to pack in more than one activity per day. This guided tour of a local Perugia winery paired with wine and local food product tasting is comprehensive but takes just a few hours, so you can enjoy yourself and then head to the day’s next adventure. Choose from multiple departure times to suit your schedule and enjoy tastings of wine and local products included.

This experience combines a tour of the Madonna del Latte winery just outside Orvieto with generous wine tastings. Take a guided walk through the vineyards and learn about the winery’s growing methods. Then, head to the wine and barrel cellars, the latter of which was carved into tuff-stone thousands of years ago. After the tour, taste four house-made wines.

Head to the Umbrian countryside for a day of fresh Italian food and cooking at an organic agriturismo (farm stay). Taking place at Il Fontanaro, this experience includes tastings of the farm’s award-winning olive oil and wine, a tour of the cellars, and a fresh pasta cooking class -- created with ingredients that you pick yourself from the garden.

Orvieto is known for its prestigious white and red wines, produced in the area’s rolling vineyards. Learn more about the history and production of local vintages with this tour and tasting at a family-run winery. Visit the vineyard and wine cellar, plus the unique barrel room that is set in an ancient Etruscan cave. End by tasting five wines paired with artisanal goat cheese sourced from a nearby organic farm.

Guided tour of the vineyards, the centuries-old olive grove and the cellar. During the tour the history of the area, its traditions and all the stages of development of the vineyard are explained, from winter pruning to the harvest. Once back in the cellar, the techniques of processing the grapes and refining the wines are illustrated, both in steel and in wood. The tasting includes the tasting of 3 labels during a light lunch based on traditional dishes. The visit lasts about 3 hours and is recommended throughout the year. Reservations required

This experience combines a tour of the Madonna del Latte winery just outside Orvieto with generous wine tastings. Take a guided walk through the vineyards and learn about the winery’s growing methods. Then, head to the wine and barrel cellars, the latter of which was carved into tuff-stone thousands of years ago. After the tour, taste four house-made wines and local cheeses and cold cuts from nearby producers.

Don't miss the opportunity to enjoy a walk in the Vineyard of Assisi and taste SAIO Assisi wines paired with exclusively local and handmade food specialties. The guided tasting let you know more about wine, the traditions and the history of this land. After the tasting let's enjoy a walk in the vineyards with a unique view on Saint Francis church just 800 mt from you,the whole city of Assisi, Santa Maria degli Angeli and Perugia on the background. The self guided-tour “Walk in the Vineyards” will guide you along the way discovering more about wine and viticulture and exploring the most panoramic area of the vineyards.

Explore a historic underground tufa cellar in Orvieto city center showcasing antique winemaking tools, old barrels and a collection of vintage bottles. Then enjoy a relaxed wine tasting, just few steps from the Duomo church. The tasting features three wines from the Umbria, each presented with tasting notes, labels, grape varieties, production methods, and interesting facts. Among the wines presented is the traditional sweet wine Vin Santo. Each wine can be paired with local specialties such as cured meats, artisanal cheeses, and typical Umbrian cookies

Immerse yourself in Spoleto’s history and culinary traditions with a walking tour and cooking class that blends culture, food, and authentic flavors. Begin with a guided stroll through Spoleto’s medieval streets, visiting local markets and food shops to discover Umbrian cuisine and its farm-to-table philosophy. After an hour of exploration, head to a local home kitchen for a hands-on cooking class. Using fresh, high-quality local ingredients, you’ll prepare classic Umbrian dishes like handmade strangozzi pasta, truffle-infused specialties, or rustic lentil soup, mastering traditional techniques passed down for generations. Once the meal is ready, enjoy your homemade feast paired with fine Umbrian wine in the cozy, welcoming atmosphere of an authentic home in Spoleto. Ideal for food lovers and cultural explorers, this experience offers new skills, authentic recipes, and unforgettable memories of Spoleto’s rich flavors.

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.

While bike tours cover a lot of ground, they can wear travelers out regardless of fitness level. This small-group tour saves you the trouble by traveling on pedal-assisted e-bikes along the backroads and country roads of the Olive Path Trail, which connects Spello to Assisi and the Umbrian Valley. Highlights include visiting the hilltop towns of Spello and Collepino, and stopping for lunch and olive oil and wine tastings at a local winery.

Discover the wine of Assisi during a tasting session, then finish on a high note with a picnic amid panoramic vineyards. Taking place at the SAIO Assisi “cantina” just outside the city, the 2-person experience starts with an intro to the estate’s wine and continues with a self-guided stroll through their vineyards to a lookout point; postcard-perfect views, a picnic of local produce, and your favorite wine awaits.

Your own private table, set among certified organic vines and ancient olive trees, overlooking a 360° panorama of the Valley of Assisi. No crowds, no shared tables — just you, the Umbrian countryside, and a guided tasting of your estate wines, single-origin olive oil and aged balsamic paired with a seasonal menu rooted in centuries of local tradition. After lunch, the estate is yours to explore freely — vineyards, olive groves, and a dedicated app that brings every cultivar to life as you wander. What Makes This Experience Truly Exclusive Your own private table — no shared seating, ever Certified organic & biodynamic estate — Assisi DOC wines ️ 360° panoramic views over the Valley of Assisi Single-origin EVO oil & aged balsamic tasting alongside wines ‍‍ Hosted by the family and their team — personal, unhurried, genuine Post-lunch vineyard walk with dedicated app Always beautiful — indoor tasting room with panoramic windows as backup

Immerse yourself in the rich culinary heritage of Umbria with a hands-on cooking class that transforms you into a chef for the day. Under expert guidance, learn to craft traditional Italian dishes using age-old techniques and fresh, seasonal ingredients sourced directly from the land. Engage in practical sessions where you’ll master the art of preparing appetizers, pasta, second courses, and delectable desserts. Conclude your culinary journey by savoring your creations, paired with a selection of local wines, all in a warm and inviting atmosphere that celebrates the true essence of Umbrian gastronomy.

What makes this experience special is the opportunity to discover Cantina Baldassarri in an authentic and direct way, through a path that combines vineyard, production and tasting. During the visit you will enter the heart of the family reality, walking through the vineyards adjacent to the winery and knowing the main phases that transform the grapes into wine, from the bunch to the glass. The tasting includes four labels representative of the production, two white wines and two red wines, selected to tell the character of the territory and the philosophy of Cantina Baldassarri. Each wine will be accompanied by bruschetta seasoned with extra virgin olive oil. An intimate and genuine experience, ideal for those who want to learn about Umbrian wine without formalities, getting in touch with the flavors, aromas and traditions of the land.

Discover organic olive oil in Umbria! Tour our olive grove, learn about cultivation, enjoy a tasting of oils, wines, bruschette, local cheeses, cured meats, and traditional desserts

Discover the world-class wines of Umbria, lesser-known but just as delicious as their Tuscan cousins. With this wine tour, visit 2 family-run wineries cellars to sample Sagrantino Montefalco DOCG, Montefalco Rosso, and other prestigious wines during informal guided tastings led by winemakers and sommeliers. Break up your tastings with a leisurely lunch featuring organic Umbrian specialties—served with local labels, of course!

Travel through the green fields and vineyards of Umbria on a trekking bike, without the inhibition of glassed-in tour bus windows. You can focus on the scenery as your guide leads the way through Bevagna and listen to commentary on the area's medieval history. Visit an organic winery for a tasting and settle down for a provided picnic lunch in a scenic spot.

This isn’t a staged activity—it’s a genuine, family-run truffle hunt led by locals who have been practicing this tradition for generations. You’re not watching… you’re part of it. The experience goes beyond the hunt. You follow trained dogs through untouched countryside, taste truffles moments after they’re found, and sit down to a farm-to-table meal where the ingredients come directly from the land around you. The setting is just as special—rolling hills, quiet forests, and spontaneous encounters with local life that you simply can’t replicate. Most importantly, it feels personal. Small groups, real connections, and an atmosphere that’s relaxed, welcoming, and completely unfiltered.

Sample two of Umbria’s most prestigious regional specialties against the backdrop of the atmospheric medieval hill town of Spello with this exclusive wine tasting and truffle lunch. Settle in at a landmark “enoteca” (wine shop” in the heart of the old town to sample regional wines and truffle-laced delicacies, as well as extra-virgin olive oil, fresh pasta, and artisan cheeses and cold cuts from the surrounding hills.

We are Alice and Alex, and we are thrilled to welcome you into our world for a unique, hands-on culinary and wine journey. Nestled in the quiet Italian countryside, our place offers the perfect, picturesque setting to slow down and connect. Together, we’ll dive into the secrets of traditional Umbrian cuisine, learning the art of making homemade pasta using only fresh, locally sourced ingredients. After the cooking session, the experience continues with a guided tasting of exceptional local wines. As you sip a curated selection from our region, we’ll share the history, passion, and unique heritage behind the winemaking process. Finally, we will sit down together to savor the dishes you created, perfectly paired with exquisite wines. It’s more than a class—it’s an unforgettable day of great food, fine wine, and shared memories in the heart of Italy. We will take a nice walk around Giove with its medieval castle and historic village.

Just 5 minutes from the historic center of Spoleto, a local hostess opens the doors of her charming countryside home to share the real heart of Umbrian cuisine. This culinary experience gives you the chance to choose the class that best suits the season and your passion — and dive hands-on into one of Italy's most beloved food traditions. Choose your experience: join the Pasta Class — available all year — or, if you are visiting in summer, book the Pizza Class Whichever you choose, the experience follows the same warm, unhurried rhythm: your hostess guides sharing techniques and stories passed down through generations. At the end of the class, everyone gathers around the table to enjoy the fruits of their labor — a full convivial meal with a traditional second course, homemade dessert, and a glass of carefully selected regional wine. More than a cooking lesson, this is an invitation to slow down, connect with the land, and take home a piece of authentic Italian life.

Immerse yourself in the natural beauty and abundance of Italy’s Umbria region on this private excursion. Visit a winery for a guided tour and wine pairing with locally cured meats in the cellar. Next, visit a traditional olive oil mill and see the process from olive to oil. Finally, sample locally produced Extra Virgin Olive Oils, and taste different varieties. This private tour is ideal for foodies and anyone looking for an authentic Italian experience.