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3573
Italy

Walking & Hiking in Idyllic Tuscany and Mystical Umbria

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.
Rating (5)
Program No. 3573RJ
Length
12 days
Starts at
4,099
Flights start at
1,000
Italy

Walking & Hiking in Idyllic Tuscany and Mystical Umbria

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.
Length
12 days
Starts at
4,099
Flights start at
1,000
Length
12 days
Rating (5)
Starts at
4,099
Flights start at
1,000
Program No. 3573RJ

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Select your type of room
Price will update based on selection
Prices displayed below are based on per person,doubleoccupancy.
DATES & starting prices
PRICES
May 6 - May 17, 2023
Starting at
4,099
May 20 - May 31, 2023
Starting at
4,099
Sep 16 - Sep 27, 2023
Starting at
4,099
Oct 7 - Oct 18, 2023
Starting at
4,099
Oct 21 - Nov 1, 2023
Starting at
4,099
DATES & starting prices
PRICES
May 6 - May 17, 2023
Starting at
4,869
May 20 - May 31, 2023
Starting at
4,869
Sep 16 - Sep 27, 2023
Starting at
4,869
Oct 7 - Oct 18, 2023
Starting at
4,869
Oct 21 - Nov 1, 2023
Starting at
4,869

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.

Best of all, you’ll…

  • In the town of Bevagna learn about two of Umbria’s finest Romanesque churches, while in Siena marvel at the medieval architecture made of sienna-colored brick.
  • 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.
Central Italy Map
by Touring Club Italiano
A regional map of Central Italy, including Tuscany, Umbria and Rome, at a scale of 1:400,000.
The Most Beautiful Villages of Tuscany
by James Bentley, Hugh Palmer (Photographer)
This handsome oversize picture book is a portrait of the Tuscan landscape and people. It contains maps, a travel guide and many color photographs.
Reluctant Saint, The Life of Francis of Assisi
by Donald Spoto
Spoto draws on fascinating new research to explore the travels, spirit and work of the beloved saint. This engaging portrait provides an excellent overview of the life of St. Francis.
Under the Tuscan Sun
by Frances Mayes
In this best-selling memoir of buying, renovating and living in an abandoned villa in Cortona, Tuscany, Mayes reveals the sensual pleasures found in rural Italy.
The Renaissance, A Short History
by Paul Johnson
The history, background, literature, sculpture, paintings and architecture of the Renaissance in just over 200 lively, thought-provoking pages.
La Bella Figura, A Field Guide to the Italian Mind
by Beppe Severgnini
Italians themselves love this guide to the Italian character, which addresses their never-ending passion for beauty, disorder and high emotion. The book opens with a snapshot of Malpensa Airport, then moves on to Tuscany, Rome, Naples and Sardinia.
Catherine of Siena, A Passionate Life
by Don Brophy
Brophy sets this deeply researched biography of the saint against the backdrop of 14th-century Europe, showing Catherine's sheer fortitude and personal magnetism in her efforts to bring peace to a troubled time.
Rough Guide Tuscany and Umbria
by Jonathan Buckley (Editor), Tim Jepson (Editor)
This comprehensive travel guide includes region-by-region descriptions and a good overview of history and culture. With chapters on Florence and surroundings -- Lucca, Pisa, Maremma, Siena, Arezzo, Peruguia, Assisi, Spoleto and Orvieto.
Songbirds, Truffles and Wolves, An American Naturalist in Italy
by Gary Paul Nabhan
The author, a poet and naturalist, heads along the Franciscan Way from Florence to Assisi. This most unusual travelogue combines natural history, spirituality and a lively appreciation of local food and food traditions. A print-on-demand paperback.
Lonely Planet Italian Phrasebook
by Lonely Planet
A handy, palm-size guide to pronunciation, basic grammar and essential vocabulary for the traveler.
Italy, A Short History
by Harry Hearder
Elegantly written, generous and informative, this compact book takes in the sweep of Italian history from the Roman Republic through the Renaissance, World War II and up to the present.
A Culinary Traveller in Tuscany
by Beth Elon
A Tuscany resident for 30 years, Elon presents 100 recipes from a hand-picked selection of favorite restaurants in this charming cookbook and travel guide. With 10 itineraries highlighting largely undiscovered regions of Tuscany, restaurants, trattorie, shops, wineries, olive oil producers, markets and food festivals.
On The Road with Francis of Assisi
by Linda Bird Francke
Assisi wandered for 20 years, affording Newsweek editor Francke and her patient husband plenty to see and do in the piazzas, sanctuaries and chapels of Assisi, Siena, Bologna, Venice, Gubbio, Rome and other choice spots.
Every Day in Tuscany, Seasons of an Italian Life
by Frances Mayes
Twenty years after "Under the Tuscan Sun," Mayes is still besotted by Italy -- her house, the tumbling geraniums, the people and the food -- all lovingly documented in her best memoir yet. With interludes in Portofino, Assisi and Rome and a focus on Renaissance master artist Luca Signorelli.
Meals
26 Meals
10 Breakfasts
7 Lunches
9 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 21, 2023 - Nov 01, 2023 (Pienza to Montefalco)
  • May 06, 2023 - May 17, 2023 (Pienza to Montefalco)
  • May 20, 2023 - May 31, 2023 (Pienza to Montefalco)
  • Sep 16, 2023 - Sep 27, 2023 (Pienza to Montefalco)
  • Oct 07, 2023 - Oct 18, 2023 (Pienza to Montefalco)
  • Oct 21, 2023 - Nov 01, 2023 (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.





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