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Self-Guided Walking : Europe

Italy: Umbria & Assisi

Easy to Moderate Terrain: 5-10 Miles Daily

Italy: Umbria & Assisi

In the geographical heart of Italy, Umbria offers the best of rural traditions and medieval grandeur in a ribbon of remarkable hilltop towns and quiet oak-forest paths. Starting in Orvieto, you’ll enjoy an adventure that sends you through fertile olive groves, UNESCO World Heritage sites, Baroque convents graced with exquisite frescoes, and Roman temples. Stay in a historic country estate lovingly updated to preserve its architectural details and delight in its sweeping views of Monte Peglia Natural Park. Walk the cobblestone streets of Spoleto, a beguiling city that dates back to pre-Roman times. Amble through a forest held sacred by the Romans and beloved by St. Francis before reaching splendid Assisi. Throughout the trip you’ll stay in boutique accommodations located just a few steps from bustling piazzas and Romanesque cathedrals. Enjoy Umbria’s cuisine, including a tasting of its renowned wines. It’s the ideal way for independent travelers to experience authentic rural Italy, and a journey that will be remembered for years to come.


Tour Highlights:
  • Savor a multi-course lunch and wine tasting at a DOC-certified vineyard in lovely Titignano, sampling local meats, cheeses, breads, and biscotti.
  • Stroll through the charming pedestrian center of ancient Orvieto, stopping by local ceramic shops, touring its dramatic 13th-century cathedral, or simply enjoying a cone of gelato.
  • Stay in a 17th-century country house set on a working family olive farm and still graced with its original details: terracotta floors, large wooden beams, and rustic stone walls.
  • Follow the Franciscan Trail as it ascends through oak forest and pastures on its way to the spectacular hilltop town of Assisi.
Tour Only

8 days, 7 nights

FROM $2,798 USD

per person, double occupancy



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  • Choose from 18 handcrafted Self-Guided Walking itineraries for 2018
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  • Generous inclusions: luggage transfers, all breakfasts, some lunches and dinners.
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  • Detailed maps and easy-to-follow route notes ensure that you’ll easily find your way.
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Itinerary & Accommodations

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Day 1

Arrival in Orvieto

Begin your trip in enchanting medieval Orvieto, perched atop steep tufa cliffs and floating like an island above Umbria’s olive groves and vineyards.

Accommodation: Hotel Duomo, Orvieto

This boutique hotel located on Orvieto’s main square offers an intimate stay just steps away from the city center’s magnificent cathedral, museums, restaurants, and shops. Guest rooms occupying three floors have been recently renovated with classic furnishings, tile floors, rich colors and fabrics, marble bathrooms, and original paintings by local artists. A gracious Italian Art-Nouveau Liberty-Style building offers welcoming public spaces displaying unique artwork and a shaded interior garden courtyard.

Day 2

Monte Peglia Natural Park

Discover why Umbria is nicknamed the “green heart of Italy” on today’s walk through the tranquil, rolling landscape of Monte Peglia Natural Park before arriving at your home for the next two nights, a secluded hilltop family farm in the countryside.

Accommodation: Podere le Corone, Monte Castello di Vibio

Perched on a hillside overlooking a picturesque valley is a peaceful 17th-century country house and working family farm, including a panoramic outdoor pool surrounded by acres of ancient olive groves. Authentic and charming guest rooms feature antique terracotta floors, large wooden beams, and stone walls. The on-site restaurant features a blend of Umbrian and Sicilian home-style cuisine featuring family recipes and the farm’s award-winning olive oil.

Day 3

Podere le Corone to Titignano

Set out through a landscape of beautiful fields, oak forests, and vineyards on your way to the day’s destination of Titignano. Here, you are welcomed in the piazza with an informal wine tasting. Enjoy exploring the hamlet’s 12th-century castle before transferring back to your accommodations.

Accommodation: Podere le Corone, Monte Castello di Vibio

Perched on a hillside overlooking a picturesque valley is a peaceful 17th-century country house and working family farm, including a panoramic outdoor pool surrounded by acres of ancient olive groves. Authentic and charming guest rooms feature antique terracotta floors, large wooden beams, and stone walls. The on-site restaurant features a blend of Umbrian and Sicilian home-style cuisine featuring family recipes and the farm’s award-winning olive oil.

Day 4

Monte Castello di Vibio to Ponte di Montemolino

Starting in the baroque piazza of Monte Castello di Vibio, you set off into the countryside of the Tiber Valley. Descending through olive groves and vineyards, your path arrives at the hilltop town of Montefalco before continuing on beside the Tiber River.

Accommodation: Palazzo Dragoni, Spoleto

This elegant property in the historical center of Spoleto, originally constructed in the mid-1500s incorporating the preexisting pre-Roman structure, is now an intimate hotel with just 14 rooms. Inside, gracious and refined common areas highlight its aristocratic heritage with classic décor, artwork, and Oriental rugs. Individually decorated guest rooms incorporate original architectural details along with antiques, pastel colors, and warm fabrics, all with a view of Monteluco Hill in the Spoleto Valley. A breakfast of homemade delicacies is served on the main floor of the historical residence, along with splendid views of the surrounding countryside.

Day 5

Spoleto loop walk along the Via di Francesco

Walking the wooded slopes of Monteluco, held sacred both by Romans and medieval Christians, follow the Via di Francesco to a 13th-century convent established by St. Francis. Continue on to the summit of Castelmonte before returning to Spoleto to explore its delicate 12th-century pink-stone cathedral, 14th-century castle, and Roman theater.

Accommodation: Palazzo Dragoni, Spoleto

This elegant property in the historical center of Spoleto, originally constructed in the mid-1500s incorporating the preexisting pre-Roman structure, is now an intimate hotel with just 14 rooms. Inside, gracious and refined common areas highlight its aristocratic heritage with classic décor, artwork, and Oriental rugs. Individually decorated guest rooms incorporate original architectural details along with antiques, pastel colors, and warm fabrics, all with a view of Monteluco Hill in the Spoleto Valley. A breakfast of homemade delicacies is served on the main floor of the historical residence, along with splendid views of the surrounding countryside.

Day 6

Valfabrica to Assisi

Following the historical Franciscan Trail, today’s walk undulates through oak forest and open pasture, past old stone farmhouses and parish churches, culminating in an exhilarating ascent to the Basilica of Assisi, one of Italy’s great pilgrimage destinations and a UNESCO World Heritage site.

Accommodation: San Crispino Residenza d’Epoca, Assisi

This historical mansion in the heart of the pedestrian center of Assisi is accessed through its 14th-century stone archway. Occupying a medieval complex surrounded by tranquil grounds and manicured gardens with views of Assisi, the residence offers just 12 fully renovated and individually decorated guest rooms. Spacious and elegant, the rooms blend original architecture with fine furnishings, fabrics, and antiques. In addition to attentive service, a free shuttle is available to the spa of its nearby sister property with a full treatment menu.

Day 7

Mount Subasio

Explore serene Mount Subasio, a haven of subtle beauty and spirituality where St. Francis famously communed with the birds. At the summit, the park’s paths emerge into meadows filled with grazing sheep, white Chianina cows, and semi-wild horses. Return to Assisi for further exploration and a celebratory dinner.

Accommodation: San Crispino Residenza d’Epoca, Assisi

This historical mansion in the heart of the pedestrian center of Assisi is accessed through its 14th-century stone archway. Occupying a medieval complex surrounded by tranquil grounds and manicured gardens with views of Assisi, the residence offers just 12 fully renovated and individually decorated guest rooms. Spacious and elegant, the rooms blend original architecture with fine furnishings, fabrics, and antiques. In addition to attentive service, a free shuttle is available to the spa of its nearby sister property with a full treatment menu.

Day 8

Departure from Assisi

Depart at your leisure for onward travel connections.

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Dates & Prices

Seasonal Tour Pricing

2018 Dates Number of Travelers
2 3 4 5 6 Single Supplement
Solo Surcharge
Apr 15 - Oct 31 $2,798 $2,698 $2,698 $2,698 $2,598 $690 $560
This tour is available daily, on request, from April 15 through October 31, 2018. Please note you may encounter particularly high temperatures in July and August. Please note that the tiered tour price is based on a guarantee of a specified number of guests—should your group decrease in size, we reserve the right to alter the per person price if necessary as reflected in the Tour Price table. Please also note that the tour price includes one arrival transfer from the train station in Orvieto to your first hotel in Orvieto. If traveling in a group of two or more with separate arrival times, additional charges will apply for multiple transfers. All prices are per person, based on double occupancy.

Seasonal Tour Pricing

2019 Dates Number of Travelers
2 3 4 5 6 Single Supplement
Solo Surcharge
Apr 15 - Oct 31 $3,298 $3,198 $3,198 $3,198 $3,098 $810 $655
This tour is available daily, on request, from April 15 through October 31, 2019. Please note you may encounter particularly high temperatures in July and August. Please note that the tiered tour price is based on a guarantee of a specified number of guests—should your group decrease in size, we reserve the right to alter the per person price if necessary as reflected in the Tour Price table. Please also note that the tour price includes one arrival transfer from the train station in Orvieto to your first hotel in Orvieto. If traveling in a group of two or more with separate arrival times, additional charges will apply for multiple transfers. All prices are per person, based on double occupancy.

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