view of vineyard in Umbria

Luxury Walking Tour of Umbria, Undiscovered Italy

Our delightful walking route 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 luxurious country inn, where the owners greet you like family, 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 $5280

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 visit his tiny monk’s cell on a secluded mountaintopa
  • 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 silvery olive groves to Montecastello and visit the smallest theatre in the world, then relax by the pool at our elegant country hotel
  • Taste Umbria’s prestigious Sagrantino wine in a private cellar, and enjoy a home-cooked meal paired with the winery’s finest vintages.

Trip Details

June-7-12, 2020

Sept dates pending, 2020

Orvieto Hotel


Best Time to Go
Spring, Summer, Fall

Single Supplement
$780 USD

Daily breakfast / 5 lunches with wine / 4 dinners with wine

Maximum Participants


Jump to Itinerary

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 lunch. Continue to the lovely hilltown of Assisi, built of pale pink stone which takes on a soft lavender glow at twilight. We’ll be staying for 2 nights in an attractive hotel built upon Ancient Roman ruins with a stunning spa. Tonight we meet the chef who prepares us a special meal based on the finest Umbrian traditions.

Day Two

We head up to the quiet green hills where St. Francis of Assisi came to meditate in such a serene setting and visit his tiny monk’s cell on a secluded mountaintop. We then cross Monte Subasio, taking an exciting 12 km (7.5 mile) walk with far-reaching views of the Umbrian plains. Tonight you are free to choose a dining spot for dinner.

Day Three

This morning we tour nearby Assisi with a local guide who takes us into the cathedral and explains the amazing restoration process of the priceless frescoes. After a relaxing farm lunch, we follow a tranquil pathway for 8 km (5 miles) to the town of Spello, and explore its flower-laden streets and curious “doors of the dead”. Continue on to our next hotel (naptime in the van!), a lovely country inn with a pool. The proprietors, Paola and Stefano, will personally welcome us. Time to relax by the pool before settling down to a leisurely dinner.

Day Four

This morning we take a 13 km (8 mile) walk through a rural 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 picnic. Continue to the perfect little village of Montecastello di Vibio, and visit the town’s impeccably restored 99-seat theatre. In the evening, we dine in an out of the way trattoria known for authentic Umbrian cuisine.

Day Five

Walk along old farm roads that lead to lovely country vistas, and enjoy a rustic lunch in an out of the way trattoria. Celebratory dinner in the nearby town of Todi, where we toast to the beauty of Umbria.

Day Six

Transfer to the Foligno or Orvieto train station. Arrivederci!

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Italian Connection

Italian Connection