Italy

Walking & Hiking in Idyllic Tuscany and Mystical Umbria

Program No. 3573RJ
Embark on a fun and informative walking exploration of Italy’s rolling hills as you discover timeless villages, famed vineyards, friendly locals and world-class cuisine.

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At a Glance

Walk and hike through the incomparable Italian countryside and get up close to the culture, history, geology, art, flora and fauna of Tuscany and Umbria. Discover not only storied beauty and panoramic views of rolling pastures, famed vineyards and olive groves, but also learn about and appreciate some of the most historic and best-preserved medieval towns, villages and monuments in Europe.
Activity Level
Outdoor: Spirited
Walking 2-6 miles daily over varied terrain; trails and dirt roads are well-marked, gently undulating with some rocky sections and steep ascents and descents. Sturdy walking/hiking shoes are required. Elevations up to 5,700 feet.
Small Group
Small Group
Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 13 to 24 participants.

What You'll Learn

  • Learn about two of Umbria's finest Romanesque churches in the town of Bevagna and marvel at the medieval architecture made of sienna-colored brick while in Siena.
  • Follow in the footsteps of Saint Francis as you visit his hermitage and explore the town of Assisi.
  • Savor the best cuisine in Tuscany at a special lunch at a mountain hut, visit renowned wineries and sample local cheeses.
Visit the Road Scholar Bookshop
You can find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
Meals
25 Meals
10 Breakfasts
7 Lunches
8 Dinners
The following choices may be available when requested in advance: Low Fat, Vegetarian, Low Salt, Gluten Free
Lodging
Lodgings may differ by date. Select a date to see the lodgings specific to that date.
Display
Oct 19, 2024 - Oct 30, 2024
  • Oct 19, 2024 - Oct 30, 2024
  • May 11, 2024 - May 22, 2024 (Pienza to Montefalco)
  • Sep 14, 2024 - Sep 25, 2024 (Pienza to Montefalco)
  • Oct 05, 2024 - Oct 16, 2024 (Pienza to Montefalco)
  • Oct 19, 2024 - Oct 30, 2024 (Pienza to Montefalco)
  • Apr 05, 2025 - Apr 16, 2025 (Pienza to Montefalco)
  • May 10, 2025 - May 21, 2025 (Pienza to Montefalco)
  • Sep 06, 2025 - Sep 17, 2025 (Pienza to Montefalco)
  • Sep 20, 2025 - Oct 01, 2025 (Pienza to Montefalco)
  • Oct 04, 2025 - Oct 15, 2025 (Pienza to Montefalco)
  • Oct 18, 2025 - Oct 29, 2025 (Pienza to Montefalco)
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.
5 nights
Pienza
The Hotel Residence San Gregorio is located in the heart of Tuscany, only a few meters away from the historical center of Pienza. Originally an opera house in the 1930s, it was partly destroyed by a bomb during World War II. After the war ended, the building was restored and turned into a cinema by the local veterans, and remained as such until the end of the 1950s. Recently renovated after several years of being abandoned, the building is now an elegant hotel in the midst of this renaissance town.
5 nights
Montefalco
The Camiano Piccolo Hotel is situated in a historic hamlet in Montefalco. Surrounded by olive trees and vineyards, and sitting 450 meters above sea level, the hotel offers a stunning panoramic view of the valley stretching from Spoleto to Perugia. Within walking distance is the historic center of Montefalco.





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