view of vineyard in Umbria

Luxury Walking Tour of Umbria, Undiscovered Italy

Our delightful walking tour through Umbria takes us through fields of flowers and silvery olive groves to the picturesque hilltowns of Orvieto, Todi, Assisi and Spello, as well as to the tiny undiscovered villages in between.  Enjoy authentic Italian hospitality at a welcoming country inn with fabulous views, or soothe your walking muscles in an historic spa once used by the ancient Romans.  We’ve selected the best rooms in intimate boutique hotels for this luxurious walking tour.  And let’s not forget Umbria’s excellent food and wine – we’ve selected some of our favorite places to eat in Umbria for this tour.  After a guided tour of Assisi we’ll enjoy a farm-to-table lunch, and in the evening, quaff the prestigious Sagrantino wine from a lofty hilltop with incredible sunset views.

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Trip Length 6 Days
Walking Level Easy to Moderate
Trip Cost $6480

Walking Levels

Our walks are rated for their level of difficulty as follows:

  • Stroll – Daily distance of 2-5 km (1-3 miles) through archeological sites and in towns with stone stairways. Footwear: Lightweight walking shoes.
  • Easy – Daily distance of 8-10 km (5-7 miles) on dirt paths and gravel roads, with short ascents & descents. Good van access for assistance along the route. Footwear: Sturdy walking shoes.
  • Moderate – Daily distance of 12-16 km (8-10 miles) with longer ascents & descents. May include cobblestone paths and steps, or narrow paths along terraced hillsides. Some van access or options for shorter walks. Footwear: Sturdy walking shoes or lightweight boots.
  • Fitness – Daily distance of 12-16 km (8-10 miles) with steep ascents & descents. Walks are at altitudes of 1200-2450 meters (3500-8000 feet) on trails and forest service roads, some rocky or exposed sections. Limited van access, options for shorter or longer routes. Footwear: Lightweight boots.
View of Todi in Umbria, Italy

“We loved touring the backstreets of every town we visited and the accommodations were so welcoming”

– C. M., U.S.A.

Trip Highlights

  • Trek through woodlands where St. Francis of Assisi came to meditate and wander through silvery olive groves
  • Stroll through the lovely town of Spello, a jumble of medieval houses built of pink limestone, and see the odd little doors of the dead
  • Walk through lush vineyards  to Montecastello and visit the smallest theatre in the world, then relax in the aromatic herb garden at our elegant country hotel
  • Taste Umbria’s culinary delights of fresh truffles, aromatic olive oil, creamy dark chocolate, and the best vintages of prestigious Sagrantino wine
  • Stay in Assisi’s top luxury hotel with an amazing spa built into ancient Roman ruins

Trip Details

Dates
April 12-17, 2025

 

Meet
Orvieto Hotel (Reached by regional train. Nearest intercontinental airport is Rome, or small aiport at Perugia)

End
Foligno Train Station

Best Time to Go
Spring, Summer, Fall

Single Supplement
Contact us for a quote

Meals
Daily breakfast / 4 lunches with wine / 4 dinners with wine

Maximum Participants
12

Accommodations
Signature & Spa

Itinerary
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Day-by-Day Itinerary

Umbria Hilltowns Placeholder
Umbria Hilltowns

Day One

Meet in the town of Orvieto, noted for its magnificent cathedral adorned in resplendent mosaics. After a scenic drive bordering Lake Corbara we take an 8 km (5 mile) walk that wanders through olive groves and woodlands before settling down to a welcome farmhouse lunch. Transfer to our boutique countryside hotel overlooking Todi, and relax in the aromatic herb garden (3 nts.) Dinner at the hotel.

Day Two

This morning we take a 13 km (8 mile) walk through a classic Umbrian landscape of stone farmhouses and vineyards, with inviting towns silhouetted on the nearby hilltops. At midday, we rest in an olive grove and indulge in a splendid lunch. Continue to the perfect little village of Montecastello di Vibio, and visit the town’s impeccably restored 99-seat theatre. Early evening walking tour of the town of Todi and dinner  in a trattoria serving authentic Umbrian cuisine near the town’s  beautiful piazza.

Day Three

Taste Umbria today! After a vineyard walk – you can choose the length  – sample  some of Umbria’s delicacies, including fresh truffles, jade green olive oil and ambrosial dark chocolate. Dinner at our hotel with the best vintages of prestigious Sagrantino wine.

Day Four

Check-out and transfer to the town of Spello, built of lovely pink limestone and known for its flower-laden streets. After exploring the town – don’t forget to note the curious “doors of the dead” as well as the vestiges of the ancient Romans – walk along a quiet route through olive groves to an agriturismo for a lunch of local specialties.  Continue to Assisi, and check-in to our luxurious 5-star hotel with an amazing spa built into Roman ruins.  Free evening for dinner.

Day Five

This morning we’ll take a guided walking tour of Assisi, where we learn the history of St. Francis and marvel at the amazing frescoes in the upper church.  Enjoy some free time to stroll the back streeets of town and have lunch. Optional walk up to the old fortress or enjoy the stunning hotel spa with its warm pool as you float by the ancient Roman columns – a unique experience!  Festive last night dinner overlooking the monuments of Assisi with our last delicious taste of Umbria’s finest wines.

Day Six

After breakfast, transfer to the Foligno train station. Arrivederci!

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