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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

Your well-being is our #1 priority

To make your experience as safe as possible, we require all participants to be fully vaccinated. See our Safety Roadmap

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Prefer to enroll or inquire by phone? 800-454-5768
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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.
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12 days
11 nights
26 meals
10 B 7 L 9 D
DAY
1
In Transit to Program
In Flight
DAY
2
Arrive Rome, Transfer to Pienza, Orientation, Welcome Dinner
Pienza
D
Hotel Residence San Gregorio

Activity note: Transfer from airport to hotel in Pienza is about 136 miles (219 km); approximately 2.5 hours. Hotel check-in from 2:00 p.m. Walking up to 1/2 mile; approximately 1.5 hours; cobblestones, city streets, and uneven pavement.

Afternoon: After meeting the group, we will transfer to the hotel Pienza for check-in and some time to settle in. Leaving our bags at the hotel, those who would like to may join the Group Leader for an introductory walk around the neighborhood in Pienza before returning to the hotel for Orientation. Orientation: The Group Leader will greet everyone and lead introductions. We will review the up-to-date program schedule, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer questions. Breakfasts will typically be European-style buffets with cold cuts, cheeses, cereals, yogurt, fruit, breads, milk, juice, coffee, tea, water. Water is included in the program cost at all meals. Periods in the schedule designated as “Free time” and “At leisure” offer opportunities to do what you like and make your experience even more meaningful and memorable according to your personal preferences. The Group Leader will be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local circumstances/conditions. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding.

Dinner: At the hotel, we’ll have plated welcome dinner with water included; other beverages available for purchase. Please note that dinners in Italy are typically later and last longer than American dinners.

Evening: At leisure. Continue getting to know your fellow Road Scholars, settle in, and get a good night’s rest for the day ahead.

DAY
3
Pienza & Its Products, Monticchello, Montepulciano
Pienza
B,L,D
Hotel Residence San Gregorio

Activity note: Walking up to 4.5 miles; approximately 3 hours; natural trails, cobblestones, and uneven pavement. Elective afternoon walk of about 4.5 miles; approximately 2 hours; trails, cobblestones, uneven paths; roughly 600 feet of elevation change. Getting on/off motorcoach; driving about 9 miles (15 km) back to Pienza; less than 1/2 hour.

Breakfast: At the hotel, the breakfast buffet offers choices such as cold cuts, cheeses, cereals, yogurt, fruit, and breads, plus milk, juice, coffee, tea, water.

Morning: We’ll set out with our Group Leader and a local expert on a walk from the hotel through beautiful Tuscany to reach Monticchiello, a small, renovated village known for its Teatro Povera (Poor Theatre). During our walk, we will see the Italian countryside, hike, and learn about the region through educational commentary.

Lunch: At a local establishment in Monticchiello, we will have a cheese tasting lunch with water, which will be accompanied by a lecture given by the cheese monger. It will focus on regional cheese making practices and produce that is prevalent in Tuscany.

Afternoon: You might like to take an elective walk through the beautiful landscape to Montepulciano. The last part of this walk can be a bit of a climb with an altitude difference of roughly 600 feet. Montepulciano is a medieval village perched on the crest of a hill of volcanic rock. Its buildings represent the iconic style of the Florentine Renaissance. Those who would rather not walk can choose to board the motorcoach and make a driving transfer to Montepulciano instead. The entire group will rendezvous in the town square and, after a walk through the town to a local winery, we’ll enjoy a wine tasting of Nobile di Montepulciano as we take in a lecture on local wines given by a local expert. We’ll then board the motorcoach and make the short transfer back to the hotel.

Dinner: Hotel plated meal.

Evening: At leisure.

DAY
4
Siena & Its History, Free Time
Pienza
B,D
Hotel Residence San Gregorio

Activity note: Getting on/off motorcoach; driving about 33 miles one way; approximately 1 hour each way. Walking up to 2 miles; approximately 3 hours; cobblestones, city streets.

Breakfast: Hotel buffet.

Morning: Transferring by motorcoach to Siena, we’ll set out on an in-depth walking field trip through this beautiful city that is draped onto hills and noted for its flamboyant ensemble of medieval buildings in honest brown (sienna-colored) brick. On the lower slopes, we will find gardens and olive groves that fill half of the space within the old city wall. Above, we’ll see Tuscany’s tallest tower and dazzling cathedral. During our walking field trip, we’ll learn from a local expert about the history of Siena.

Lunch: This meal has been excluded from the program cost and is on your own to enjoy what you like. The Group Leader will be happy to offer suggestions.

Afternoon: Free time. This period of time has been set aside for your personal independent exploration to see and do what interests you most. Please refer to the list of Free Time Opportunities. The Group Leader will be happy to offer suggestions. We’ll meet at a predetermined point and return to the hotel via motorcoach.

Dinner: Hotel plated meal.

Evening: At leisure.

DAY
5
Monte Amiata & The Tuscan Mountains
Pienza
B,L,D
Hotel Residence San Gregorio

Activity note: Getting on/off motorcoach; driving about 29 miles one way; approximately 1 hour each way. Walking up to 5 miles; approximately 4.5 hours; natural trails; elevation change of roughly 1,300 feet.

Breakfast: Hotel buffet.

Morning: Boarding the motorcoach, we’ll ride to Monte Amiata at 5,700 feet, the highest point and only “real” mountain in southern Tuscany. The mountainous landscape is covered with thick chestnut and beech forests, crisscrossed with brooks and streams. A broad-based mountain, Monte Amiata is visible for miles from the low hills with a well-maintained trail system in a gorgeous countryside. A circle of towns rings its lower slopes. The delightful spring-fed pools here belong to a geometrical system that more or less encircles Monte Amiata as well, producing an abundance of natural springs. This morning’s walk will include a bit of a climb; however, the scenery is well worth the effort. During the field trip, we’ll take in commentary about the Apennine nature and volcanic origins of the area.

Lunch: At a mountain hut known for serving some of the best food in southern Tuscany, we will enjoy delicious plated meals with water included; wine available for purchase.

Afternoon: We’ll then continue our walk on Monte Amiata with commentary, learning about the history of the area including cultural details, as well as information regarding the local flora and fauna. Then take a coach to the medieval hamlet of Bagno Vignoni for the chance to dip your feet in the warm, soothing water of its natural hot springs. People have been enjoying these famous "spas" since the Renaissance. Walk back to the hotel.

Dinner: Hotel plated meal.

Evening: At leisure.

DAY
6
Montalcino Walk, Bagno Vignoni Hot Springs
Pienza
B,L
Hotel Residence San Gregorio

Activity note: Getting on/off motorcoach; driving about 14 miles one way; approximately 1/2 hour each way. Walking up to 4 miles; approximately 5 hours; cobblestones, city streets, and natural trails.

Breakfast: Hotel buffet.

Morning: Traveling by motorcoach, we’ll journey to Montalcino, home of the famous Brunello wine. After a short walking field trip through Montalcino with our Group Leader, during which we will learn about the region and this quintessential Italian town, we’ll walk through vineyards towards the Abbey of St. Antimo in the center of this charming valley.

Lunch: At the local restaurant, or osteria, we’ll taste some of their offered specialties, with wine and water included.

Afternoon: After lunch, enjoy a short walk to a local winery for a wine tasting.

Dinner: On your own to explore more of the local fare.

Evening: At leisure. Prepare for check-out and transfer in the morning.

DAY
7
Transfer to Montefalco via Perugia
Montefalco
B,D
Camiano Piccolo Hotel

Activity note: Getting on/off motorcoach; driving about 80 miles total throughout the day; approximately 2 hours; stops for field trips. Walking up to 2 miles; approximately 3 hours; cobblestones, city streets, and uneven pavement.

Breakfast: Hotel buffet.

Morning: Once checked out of the hotel, we will board the motorcoach for transfer along the banks of Lake Trasimeno to Perugia where we will make a stop for a city walk led by our Group Leader. Perugia is one of the 12 Etruscan city-states and is the regional capital. It also has one of the largest state universities in the country.

Lunch: On your own sample the regional fare.

Afternoon: We’ll complete our transfer to Montefalco and check into the hotel. Upon arrival, we’ll set out for an introductory walk in the neighborhood. With our Group Leader, we’ll learn about the history of the town as we see where the nearest points of interest are including ATMs, pharmacies, etc.

Dinner: At the hotel, we’ll have plated meals with water included; other beverages available for purchase.

Evening: At leisure.

DAY
8
Sagrantino Wine Country, Montefalco
Montefalco
B,L,D
Camiano Piccolo Hotel

Activity note: Walking up to 6 miles; approximately 4.5 hours; natural trails and city streets.

Breakfast: At the hotel, the breakfast buffet offers choices such as cold cuts, cheeses, cereals, yogurt, fruit, and breads, plus milk, juice, coffee, tea, water.

Morning: On a walking field trip led by our Group Leader through Montefalco and the famous Sagrantino wine country, we’ll make our way along a river with vineyards as we listen to commentary about local wines. The origins of these wines go back to Etruscan times and are among the most important Italian red wines today. Continuing, we’ll traverse the slopes of Montepennino overlooking the entire Umbrian vale.

Lunch: At a local winery, we’ll have a meal together with wine and water included.

Afternoon: After some to explore the wine estate independently, we will then walk back to Montefalco and take some time for independent exploration.

Dinner: Hotel plated meal.

Evening: At leisure.

DAY
9
St. Francis’ Hermitage, Assisi Walk, Basilica St. Francis
Montefalco
B,L,D
Camiano Piccolo Hotel

Activity note: Getting on/off motorcoach; driving about 20 miles one way; approximately 1.5 hours roundtrip. Walking up to 3.5 miles; approximately 2 hours; cobblestones, uneven pavement, and natural trails.

Breakfast: Hotel buffet.

Morning: Transferring by mtorcoach, we’ll make our way to St. Francis’ Hermitage for a field trip, during which we will learn from a local expert about the life and impact of St. Francis of Assisi. Afterwards, we will walk down to Assisi for a stroll through this famous town as we enjoy the tranquil back streets and homes with geranium-filled window boxes. Assisi is visible for miles around, tucked under the ridge of Monte Subasio. Depending on our group pace, we may get to see most of the sights of Assisi in one day.

Lunch: At a local establishment in Assisi.

Afternoon: Next, we’ll walk to the Basilica St. Francis for a field trip led by a monk who lives in the monastery. St. Francis was born in Assisi in 1182 and died in 1226 at the age of 44. Construction began on the basilica when he was canonized as a saint a mere two years after his death; it was completed in 1253. As founder of the mendicant Franciscan order of Catholic monks, St. Francis is depicted in the church’s abundant Early Renaissance fresco paintings by many artists such as Giotto and Cimabue. We’ll then return to the hotel via private motorcoach.

Dinner: Hotel plated meal.

Evening: At leisure.

DAY
10
Monte Patrico & Valnerina Mountains, Truffle Walk, Spoleto
Montefalco
B,L,D
Camiano Piccolo Hotel

Activity note: Getting on/off motorcoach; driving about 43 miles total throughout the day; approximately 1.5 hours total; stops for field trips. Walking up to 4 miles total; approximately 3.5 hours; natural trails, cobblestones, and uneven pavement; elevation decrease of roughly 1,260 feet from Monteluco to Spoleto.

Breakfast: Hotel buffet.

Morning: Upon arrival by motorcoach to Monte Patrico at about 3,340 feet, we’ll go a farm estate in the mountains where we will go on a truffle hunt with the farm owner and his truffle dogs. Monte Patrico is located above the town of Spoleto on the summit of the Valnerina Mountains, which are known for their rugged beauty. Before setting out on the truffle hunt, we will gather with the farm owner and listen to a field lecture all about truffles.

Lunch: At the farm with our host farmers.

Afternoon: This afternoon, we’ll transfer to the woods of Monteluco and walk down to Spoleto, one of Umbria’s loveliest hill towns. In Spoleto, we will view the Ponte delle Torri, a bridge and aqueduct of 10 towering arches that links Spoleto with the slopes of Monteluco and is arguably one of the greatest engineering works of The Trecento (14th century Italy). We’ll walk to the upper part of the town center and take the motorcoach back to Montefalco.

Dinner: Hotel plated meal.

Evening: At leisure.

DAY
11
Gualdo Cattaneo, Olive Mill, Bevagna Walk, Medieval House
Montefalco
B,L,D
Camiano Piccolo Hotel

Activity note: Getting on/off motorcoach; driving about 19 miles total throughout the day; less than 1 hour total; stops for field trips. Walking up to 4.5 miles; approximately 3.5 hours; cobblestones, city streets, and natural trails.

Breakfast: Hotel buffet.

Morning: Transferring to Gualdo Cattaneo, we’ll go for a short visit to this medieval fortified village where we’ll learn about Umbrian history from our Group Leader during the walk through the hamlet. Afterwards, we’ll walk through the farmland and woods to an olive mill where we will learn about olive oil production.

Lunch: At the family-run mill.

Afternoon: Next, we’ll travel to the serene and handsome medieval town of Bevagna, a city older than Rome that has two of Umbria's finest Romanesque churches. While here with a local expert, we’ll visit the permanent exhibition of the Medieval House while listening to commentary about local life in the Middle Ages compared to the Roman Age. We’ll then return to the hotel.

Dinner: At the hotel, we’ll have a farewell meal together. Share some of your favorite experiences with new Road Scholar friends.

Evening: At leisure. Prepare for check-out and departures in the morning.

DAY
12
Transfer to Rome, Program Concludes
In Flight
B

Activity note: Hotel check-out by 11:00 a.m. See your program’s “Transportation Information” regarding transfers. Getting on/off motorcoach; driving about 115 miles (185 km) to Rome airport; approximately 2.5 hours.

Breakfast: Hotel buffet.

Morning: Once checked out of the hotel, we will board the motorcoach for transfer back to the airport in Rome. This concludes our program. If you are returning home, safe travels. If you are staying on independently, have a wonderful time. If you are transferring to another Road Scholar program, detailed instructions are included in your Information Packet for that program. We hope you enjoy Road Scholar learning adventures and look forward to having you on rewarding programs in the future. Don’t forget to join our Facebook page and follow us on Instagram. Best wishes for all your journeys!






Important registration tip:
If you want to attend the live lecture, please do not wait until the last minute to enroll.
If you enroll after a lecture is complete, we’ll send you a recording of the event.