Day 1 - Welcome to Timeless Orvieto

Your Umbrian journey begins with a private transfer from Rome (Fiumicino or Ciampino airports), Florence, or another arrival point, bringing you through the peaceful landscapes of central Italy towards the dramatic hilltop town of Orvieto.

Perched high above the countryside on a volcanic plateau, Orvieto offers one of Italy’s most unforgettable arrivals. After settling into your elegant boutique accommodation within or close to the historic center, take time to discover the town at a relaxed pace.

Wander through beautifully preserved medieval streets, where artisan workshops, local boutiques and charming cafés create an authentic atmosphere. Visit the magnificent Duomo, one of Italy’s greatest Gothic masterpieces, before discovering the fascinating underground city carved into volcanic rock over centuries.

As the afternoon light spreads across the Umbrian hills, enjoy a quiet aperitivo overlooking the countryside before your first dinner celebrating regional specialties, handmade pasta and Orvieto’s renowned white wines.

A gentle and memorable introduction to Umbria, where history, landscapes and authentic Italian living come together.

Day 2 - Civita di Bagnoregio & The Ancient Heart of Umbria

Today you will discover one of central Italy’s most extraordinary hidden treasures: Civita di Bagnoregio, a magical medieval village suspended above dramatic valleys.

Leaving Orvieto behind for a scenic countryside drive, you will reach this remarkable hilltop town, accessible only by its iconic pedestrian bridge. As you cross towards the village, the views over the surrounding landscape create one of the most memorable moments of your journey.

Explore the quiet stone lanes, ancient buildings and panoramic viewpoints of a place that feels frozen in time. Continue into the Etruscan heartland, discovering the fascinating history of the civilizations that shaped this region long before Rome.

Enjoy a relaxed countryside lunch featuring seasonal ingredients, local cheeses, handmade specialties and regional wines. Depending on the season, the afternoon can include a private visit to a boutique vineyard to meet local producers and taste Umbrian wines in an intimate setting.

Return to Orvieto in the late afternoon and enjoy another evening immersed in the charm of this remarkable medieval town.

Day 3 - Lake Trasimeno & The Art of Slow Living

Today you leave Orvieto and move to your second base: 3 nights in the countryside near Assisi or Perugia.

After three memorable nights in Orvieto, your journey continues north through some of Umbria’s most beautiful landscapes. A private transfer takes you towards your new countryside retreat, with a wonderful stop along the way at Lake Trasimeno.

Discover the peaceful beauty of Umbria’s largest lake, where traditional fishing villages, olive groves and gentle hills create a landscape of remarkable serenity. Enjoy a private boat experience across the calm waters, with time to discover small islands and centuries-old monasteries surrounded by nature.

A leisurely lakeside lunch celebrates the flavors of the region, with fresh local ingredients, traditional recipes and exceptional olive oil.

Continue towards your elegant countryside accommodation near Assisi or Perugia, ideally located to explore northern Umbria while enjoying the tranquility of vineyards and rolling hills.

The afternoon is intentionally relaxed, allowing time to settle in, enjoy the property and embrace the slower rhythm of Italian countryside life.

Day 4 - Assisi: Art, Beauty & Spiritual Heritage

Today is dedicated to Assisi, one of Italy’s most inspiring hill towns and a masterpiece of art, architecture and spirituality.

Arrive in this beautifully preserved medieval town surrounded by breathtaking views over the Umbrian Valley. Discover the Basilica of Saint Francis, a UNESCO World Heritage Site and home to extraordinary frescoes by Giotto and other masters of the early Renaissance.

Beyond its artistic treasures, Assisi invites you to slow down and explore its peaceful atmosphere: flower-filled streets, stone arches, hidden chapels and quiet corners that reveal centuries of history.

Enjoy lunch in a refined countryside restaurant nearby, surrounded by vineyards and olive trees, before returning to your retreat.

The afternoon remains free to relax and enjoy your surroundings, whether by the pool, in the gardens or simply taking in the beauty of the Umbrian countryside.

Day 5- Wine, Truffles & The Flavors of Umbria

Today immerses you in the culinary traditions that make Umbria one of Italy’s most authentic gastronomic regions. Travel through the rolling hills surrounding Montefalco, where vineyards, olive groves and medieval villages create a spectacular countryside setting. Meet a local wine producer for a private tasting experience and discover Sagrantino, Umbria’s celebrated native grape variety known for its richness and character.

Depending on the season, join a truffle hunting experience accompanied by expert guides and trained dogs, exploring the forests and landscapes where this precious ingredient is found.

A memorable gourmet lunch follows, showcasing the finest seasonal products of the region. Continue with an olive oil experience to discover the craftsmanship behind Umbria’s exceptional extra virgin olive oils.

Return to your countryside retreat in the afternoon with time to relax and enjoy the peaceful surroundings of your accommodation.

Day 6 - Perugia & Farewell to Umbria

Before leaving Umbria, discover Perugia, the elegant regional capital known for its medieval heritage, artistic treasures and vibrant atmosphere.

Stroll through the historic center, where ancient arches, Renaissance palaces and charming streets reveal the many layers of the city’s fascinating past. Explore the medieval squares, discover sections of the ancient Etruscan walls and enjoy the unique atmosphere of this sophisticated yet authentic Italian city.

Take time for a final relaxed lunch in a beautiful historic piazza, followed by a last coffee or some artisan shopping before departure.

Your private driver will then take you to your next destination or airport, with connections possible to Rome, Florence or Perugia depending on your travel plans.

As you leave Umbria, you take with you memories of extraordinary landscapes, welcoming local communities, exceptional cuisine and a slower, more authentic way of experiencing Italy.

A journey designed not only to be visited, but truly experienced.