Italy

The Hidden Medieval Villages of Tuscany and Umbria

Program No. 22977RJ
Go off the beaten path to discover the charming, lesser-known villages of Tuscany and Umbria. Learn about Roman history, sample delicious regional food and much more!

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At a Glance

The villages of Tuscany and Umbria have their own pace — a relaxed philosophy that flows along the colorful hillsides, quiet towns and timeless landscapes. Discover these idyllic regions as you explore the piazzas, churches and fortresses of Italy’s quieter gems that are often away from the flow of tourists. From Siena to the underground tunnels of Orvieto, the secrets of the Italian countryside wait to be discovered!
Activity Level
Keep the Pace
Walking up to two and half miles; some uneven ground and cobblestones. Stairs without railings.
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

  • Explore the Southern part of Tuscany, the Val D'Orcia, rich in beauty and charm.
  • Delight in a field trip to the Collegio del Cambio in Perugia to admire Perugino's frescoes.
  • Discover the mysteries of Orvieto, a hilltop village renowned for its Cathedral of St. Mary of Assumption and the underground caves that were dug beneath the city 2,500 years ago.
Featured Expert
All trip experts
Profile Image
Mick Plewman
Mick Plewman is an exploration leader with more than 20 years of experience working all over the world, from Central America to Sri Lanka. He is also a qualified teacher and educational psychologist who worked in the British school system and for the British Army. Mick has lived in Central Italy for more than two decades, where he is renovating an old farmhouse in Umbria. He enjoys traveling, reading, and studying the art and history of the many places he visits.

Please note: This expert may not be available for every date of this program.

Profile Image of Mick Plewman
Mick Plewman View biography
Mick Plewman is an exploration leader with more than 20 years of experience working all over the world, from Central America to Sri Lanka. He is also a qualified teacher and educational psychologist who worked in the British school system and for the British Army. Mick has lived in Central Italy for more than two decades, where he is renovating an old farmhouse in Umbria. He enjoys traveling, reading, and studying the art and history of the many places he visits.
Profile Image of Ilaria Fiore
Ilaria Fiore View biography
Ilaria Fiore was born in Milan, where she studied languages (English, German, Spanish) and graduated in art history at the State University with a thesis focused on the Cathedral of the City (Duomo) in the Napoleonic period. She decided to turn her passion for travel into a profession, obtaining licenses related to leading groups as well as a master's degree in food and wine tourism. She has also taught art and literature as a substitute teacher, and is an amateur actress.
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Year
2025
  • 2024
  • 2025
Date and Direction
May 05 - May 16 (Siena to Roma Fiumicino)
  • Jan 13 - Jan 24 (Siena to Roma Fiumicino)
  • Jan 27 - Feb 07 (Siena to Roma Fiumicino)
  • Feb 17 - Feb 28 (Siena to Roma Fiumicino)
  • Mar 17 - Mar 28 (Siena to Roma Fiumicino)
  • Apr 07 - Apr 18 (Siena to Roma Fiumicino)
  • Apr 28 - May 09 (Siena to Roma Fiumicino)
  • May 05 - May 16 (Siena to Roma Fiumicino)
  • May 19 - May 30 (Siena to Roma Fiumicino)
  • Jun 02 - Jun 13 (Siena to Roma Fiumicino)
  • Sep 01 - Sep 12 (Siena to Roma Fiumicino)
  • Sep 15 - Sep 26 (Siena to Roma Fiumicino)
  • Sep 22 - Oct 03 (Siena to Roma Fiumicino)
  • Oct 06 - Oct 17 (Siena to Roma Fiumicino)
  • Oct 13 - Oct 24 (Siena to Roma Fiumicino)
  • Oct 20 - Oct 31 (Siena to Roma Fiumicino)
  • Nov 03 - Nov 14 (Siena to Roma Fiumicino)
  • Nov 10 - Nov 21 (Siena to Roma Fiumicino)
Please Note: The program differs on certain dates.
Please Note: The program differs on certain dates.
Select trip year and date
2025
  • 2024
  • 2025
May 05 - May 16 (Siena to Roma Fiumicino)
  • Jan 13 - Jan 24 (Siena to Roma Fiumicino)
  • Jan 27 - Feb 07 (Siena to Roma Fiumicino)
  • Feb 17 - Feb 28 (Siena to Roma Fiumicino)
  • Mar 17 - Mar 28 (Siena to Roma Fiumicino)
  • Apr 07 - Apr 18 (Siena to Roma Fiumicino)
  • Apr 28 - May 09 (Siena to Roma Fiumicino)
  • May 05 - May 16 (Siena to Roma Fiumicino)
  • May 19 - May 30 (Siena to Roma Fiumicino)
  • Jun 02 - Jun 13 (Siena to Roma Fiumicino)
  • Sep 01 - Sep 12 (Siena to Roma Fiumicino)
  • Sep 15 - Sep 26 (Siena to Roma Fiumicino)
  • Sep 22 - Oct 03 (Siena to Roma Fiumicino)
  • Oct 06 - Oct 17 (Siena to Roma Fiumicino)
  • Oct 13 - Oct 24 (Siena to Roma Fiumicino)
  • Oct 20 - Oct 31 (Siena to Roma Fiumicino)
  • Nov 03 - Nov 14 (Siena to Roma Fiumicino)
  • Nov 10 - Nov 21 (Siena to Roma Fiumicino)
While we make every effort to ensure the accuracy of our published materials, programs are typically advertised more than a year prior to their start date. As a result, some program activities, schedules, accommodations, personnel, and other logistics occasionally change due to local conditions or circumstances. Should a major change occur, we will make every effort to alert you. For less significant changes, we will update you during orientation. Thank you for your understanding.
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12 days
11 nights
22 meals
10 B 4 L 8 D
DAY
1
In Transit to Program
In Flight
DAY
2
Arrive Florence, To Siena, Orientation, Welcome Dinner
Siena
D
NH Siena

Activity note: Hotel check-in available from 03:00 p.m. Remember to bring your nametag (sent previously)

Afternoon: After checking-in at the hotel and getting your room, take some time to freshen up and relax before our Orientation session. 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 in our program will be hearty buffets; most lunches and some other meals will be two courses featuring local dishes. These are the names of typical food courses in Italy: l'antipasto, a hot or cold appetizer; il primo piatto, the first course, often soup or pasta; il secondo piatto, the second course or main dish; il contorno piatto, a side dish such as vegetables or salad; and il dolce, dessert. Periods in the daily 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.

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

DAY
3
Siena, Lecture, Free Time
Siena
B,L
NH Siena

Activity note: Walking up to 2.5 miles, approximately 2 hours; standing up to 1 hour; generally cobblestone and hilly terrain.

Breakfast: At the hotel.

Morning: We will begin our learning adventure in Siena with an expert-led walking field trip through the historical center. Siena is a Gothic Dream and a UNESCO World Heritage Site. We will enjoy an on-site lecture on Siena's Romanesque-Gothic Architecture. We will visit the gothic Basilica of San Domenico, which preserves a very important relic, the head of Saint Catherine. We will follow the path of the Francigena route, along which we can admire important buildings, such as the headquarters of Monte dei Paschi, the oldest bank in Europe, the Palazzo Tolomei and Palazzo Chigi Saracini seat of the Music Accademy, Accademia Chigiana. We will visit the Cathedral of the Assumption, a jewel of Gothic architecture, but not only, as it contains the famous works of Michelangelo, Donatello and Bernini. Our walk will end in the Piazza del Campo, where twice a year the famous horse race, Palio di Siena, takes place.

Lunch: At a restaurant in Siena.

Afternoon: We will enjoy some free time in Siena. This period of time has been set aside for your personal independent exploration to see and do what interests you most. The Group Leader will be happy to offer suggestions. Please note that the period scheduled for free time is subject to change depending on local circumstances and opportunities for independent exploration.

Dinner: 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.

Evening: At leisure.

DAY
4
Montalcino, Lecture, Winery, Pienza
Siena
B,L,D
NH Siena

Activity note: Getting on/off a motorcoach; driving about 80 miles throughout the day, approximately 2.5-hour riding time. Walking up to 3 miles, approximately 2 hours; standing up to 1 hour, opportunities to sit, restrooms available; generally flat terrain.

Breakfast: At the hotel.

Morning: We’ll embark with our Group Leader on a field trip to Montalcino and see the Town Hall, the arcades of the Piazza del Popolo and the Church of Saint Egidio. We will enjoy an on-site lecture focused on Italy's Gems, the Medieval Villages, History, Culture and Traditions. We will ride to a local winery for a Tuscan wine experience.

Lunch: At the winery. We'll taste a Tuscany wine paired with a selection of typical products of the region.

Afternoon: We will ride to Pienza, We will embark with our Group Leader on a walk through the medieval alleys that open on breathtaking view of the Val D'orcia, We will discover magnificent Renaissance buildings: the residences of the Pope Pius II Piccolomini, the Cardinals Borgia, Ammannati and Jouffroy d’Arras. In the heart of the city, we will visit the majestic Cathedral of Santa Maria Assunta, commissioned by Pius II and realized by the architect Bernardo Rossellino form 1459 to 1462. We’ll return to the hotel.

Dinner: At the local restaurant.

Evening: At leisure.

DAY
5
Volterra, San Gimignano
Siena
B,D
NH Siena

Activity note: Getting on/off a motorcoach; driving about 85 miles throughout the day, approximately 2.5 hours riding time Walking up to 2.5 miles throughout the day; generally flat terrain.

Breakfast: At the hotel.

Morning: We’ll embark on a field trip to Volterra, a town of artistic and historic heritage, and a land filled with art and nature. We will begin our learning adventure with a walking field trip with our Group Leader through Volterra and visit the Cooperativa Artieri Alabastro. A historic entity that strives to keep alive the Volterra tradition of alabaster craftsmanship. We will get to know the different steeps involved in the processing of the alabaster stone.

Lunch: On your own in Volterra.

Afternoon: We will ride to San Giminano. We will embark with our Group Leader on a walk through the city of 13 towers; once, in the Middle Age there were 72 towers, one for each family. We will then return to the hotel.

Dinner: At a local restaurant.

Evening: At leisure.

DAY
6
Cortona
Siena
B,L,D
NH Siena

Activity note: Getting on/off a motorcoach; driving to Cortona is about 88 miles, approximately 2 hours. Walking up to 2 miles; hilly terrain to reach the city center from parking than flat terrain and than downhill.

Breakfast: At the hotel.

Morning: Our field trip today is to Cortona. We will begin our learning adventure with an expert-led walking field trip through this scenic Tuscan hill town with great art, great atmosphere, and superb views. We will visit the Diocesan Museum, an art museum in Cortona, located on the former site of the local Church of Gesù. It houses works of art by artists such as Luca Signorelli and Sassetta.

Lunch: At a restaurant in Cortona.

Afternoon: The afternoon is free before returning to the hotel.

Dinner: At the hotel.

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

DAY
7
Gubbio, To Spoleto
Spoleto (PG)
B,D
Hotel Dei Duchi

Activity note: Getting on/off a motorcoach; driving about 150 miles throughout the day, approximately 3 hours riding time. In Gubbio walking up to 2 miles; hilly, several city elevators.

Breakfast: At the hotel.

Morning: After checking out of the hotel, we will board our private motorcoach and transfer to Spoleto, where we will check in at our hotel. We will stop en route at Gubbio. we will embark on an expert-led waling field trip of Gubbio. Gubbio is beautifully located on the lower slopes of Mt. Ingino. Gubbio is an extremely ancient town mentioned in the famous Eugubine Tablets and was in the past the capital of Umbria. Gubbio's compact town centre has a good selection of mediaeval, Gothic, and Renaissance structures built of gray limestone, with great views over the beautiful countryside.

Lunch: On your own to enjoy what you like in Gubbio

Afternoon: We expect to arrive in Spoleto in the early afternoon when we will check in to the hotel.

Dinner: At the hotel.

Evening: At leisure.

DAY
8
Spoleto
Spoleto (PG)
B,D
Hotel Dei Duchi

Activity note: Walking up to 2 miles throughout the day; generally flat terrain, some hilly sections.

Breakfast: At the hotel.

Morning: We will begin our learning adventure with an expert-led walking field trip through Spoleto and visit the Cathedral with frescoes by Filippo LIppi and Pintoricchio and the Church of Santa Eufemia

Lunch: On your own to enjoy what you like in Spoleto.

Afternoon: The remainder of the afternoon is free.

Dinner: At a local restaurant.

Evening: At leisure.

DAY
9
Assisi, Free Time
Spoleto (PG)
B,L
Hotel Dei Duchi

Activity note: Getting on/off a motorcoach; driving about 60 miles throughout the day, approximately 1 hour riding time. Walking throughout the day approximately 3 miles. In Assisi, flat terrain, escalators to reach the top; some cobblestone alleys in Assisi.

Breakfast: At the hotel.

Morning: Our field trip of the day will be to Assisi, home of St. Francis (1181-1226). We will walk with a local expert among the medieval houses and shops, on cobblestone streets and alleys to reach the Basilica of St. Francis (Basilica Papale e Sacro Convento di San Francesco). The Basilica is first of all a holy place as the lower sanctuary contains the tomb and shrine of St. Francis. In the upper church, we can admire magnificent frescos of Giotto and his school, based on stories of St. Francis.

Lunch: At a restaurant in Assisi.

Afternoon: We will enjoy some free time in Assisi. We’ll then return to Spoleto.

Dinner: On your own to enjoy what you like.

Evening: At leisure.

DAY
10
Perugia, Free Time
Spoleto (PG)
B,D
Hotel Dei Duchi

Activity note: Getting on/off a motorcoach; driving about 80 miles throughout the day, approximately 1.5 hour riding time. In Perugia, walking up to 2 miles throughout the day, generally flat terrain with some flights of stairs.

Breakfast: At the hotel.

Morning: We will ride to Perugia, the lively medieval walled hill town with historic buildings, modern shops and a notable artistic center. We will visit with our Group Leader the town and the Moretti Caselli laboratory where they restore the stained-glass windows. We will enjoy some free time.

Lunch: On your own in Perugia.

Afternoon: In the early afternoon we will visit the Collegio del Cambio to admire the Perugino' frescoes before returning to the hotel.

Dinner: At a local restaurant.

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

DAY
11
Orvieto, To Rome-Fiumicino, Free Time
Roma Fiumicino
B,D
Hotel Isola Sacra

Activity note: Getting on/off a motorcoach; driving about 160 miles throughout the day, approximately 3 hours riding time. Walking in Orvieto approximately 2 miles; generally flat terrain.

Breakfast: At the hotel.

Morning: After checking out of the hotel, we will board our private motorcoach and begin our transfer to Rome-Fiumicino. En route, we will stop at Orvieto for an expert led field trip of the town included the entrance to the Cathedral. Orvieto sits atop a cliff of tuff (rock formed by the consolidation of volcanic ash) overlooking the Paglia River valley. It was originally an Etruscan settlement from between the 9th and 8th centuries C.E. Its main attraction is the iconic Duomo — Cathedral of St. Mary of the Assumption — an artistic masterpiece of the late medieval era. This is one of the most famous cathedrals in Italy. In addition to the amazing façade, the St. Brizio Chapel contains frescoes painted by Luca Signorelli that influenced Michelangelo’s rendition of “The Last Judgment” in this Sistine Chapel. You will have time on your own to explore the Underground, a maze of more than a thousand caves, tunnels, and wells dug out of the rock over more than 2,500 years and used for a variety of purposes. There are the remains of oil presses, wine cellars, kilns, cells for pigeons, storage areas, and many wells connected to tanks to supply water.

Lunch: On your own in Orvieto to enjoy what you like.

Afternoon: Continuing our transfer, we expect to arrive in Rome-Fiumicino in the late afternoon and check in to our final hotel.

Dinner: At the hotel. We’ll share some of our favorite experiences from the program with fellow Road Scholars

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

DAY
12
Program Concludes
In Flight
B

Activity note: Hotel check out by 11:00 a.m. See your program’s "Getting There" information regarding transfers.

Breakfast: At the hotel depending on departure time. This concludes our program.

Morning: 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 another rewarding program in the future. Don’t forget to join our Facebook page and follow us on Instagram. Best wishes for all your journeys!






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