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Teaching a Classical Education

Teaching a Classical Education

Teaching a Classical Education

An intensive educational program for teachers and administrators of classical learning.

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An intensive educational program for teachers and administrators of classical learning.

The Virtues and Vices in Classical, Medieval, and Renaissance Tradition

Led by the program leader, Dr. John Skillen, you will focus on three topics in particular: the cultivation of the virtues in students; the historic church’s digestion of the classical heritage; and the presence of the virtues in pre-modern visual art and architecture.

Tour Price:
Tour Dates:

June 1 - 9, 2024


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Day 1

Arrival, Introduction, and Orientation

After settling into our lodgings in Monastery San Lodovico, we will gather fellow attendees and conference leaders for an orientation to the upcoming week’s activities.

Our first meeting will be followed by a stroll through the town of Orvieto with conference leader, Dr. John Skillen, concluding with a traditional Italian meal at Locanda del Lupo.

Day 2

The Virtues: An Historical Overview


An overview of the tradition of the virtues and vices in philosophy, literature, and the visual arts (with brief guest appearances by Plato, Aristotle, Cicero, Thomas Aquinas, Dante, Boccaccio, Chaucer, Giotto, Lorenzetti, Michelangelo, and others). This seminar will take place in the monastery library.

Guided Tour:

This afternoon we will become familiar with the town of Orvieto, Urbs Vetus, the old city, as it was once called in Latin, by way of its churches and civic buildings, piazzas and palazzi, convents and monasteries, shops and cafès. We make our first visit to the Duomo: the 14th-century cathedral, richly decorated, and its Chapel of San Brizio, frescoed with scenes from classical writers, Dante’s Divine Comedy, the End Times and the Last Judgment, and the choir of saints singing the Te Deum–one of the most acclaimed fresco cycles of Renaissance Europe.


How does sophisticated visual art exercise its effect on our sensibility (and on our moral compass and character)?

Day 3

Justice, Wisdom, and Beauty in the Italian City State

Excursion: Siena

This morning we’ll travel to Siena, medieval arch rival of Florence, exuberant in style and art. Focusing on the two main piazzas, we will visit the black-and-white striped Duomo, the town hall (Palazzo Pubblico) with its frescoes of Good and Bad Government framing the council chamber of the Nine, and the medieval hospital (Ospedale), with the works of mercy depicted on the frescoed walls of the great hall.


We’ll return to Monastery San Ludovico for an evening conversation about Virtue (and Vice) in the Public Square: then and now.

Day 4

The Italian Family and the Importance of Place


The morning will be free for those wishing to join Dr. Skillen to attend a Sunday mass either in the majestic Duomo or in the beloved parish church of San Giovenale (named for the evangelist who brought the faith to southern Umbria), where worship has continued since its founding in 1004.

Local excursion:

Today we’ll honor the day of rest with an invigorating country walk to the Cappucchin monastery on the opposite hill, with stupendous vista of Orvieto, or with a visit to a local family winery in their ancestral villa, a one-time medieval monastery built over the fifth-century Etruscan foundations. The quiet theme of the day: the continuity of place and community, rich with resonance.


A Socratic conversation, taking up these topics:

  • How can, might, should we teach virtue?
  • What is the difference between teaching about the virtues and fostering virtue?
  • In what ways does virtue relate to civic responsibility and engagement?
Day 5

Medieval and Renaissance Florence

Excursion: Florence

This morning we’ll depart for the great medieval and renaissance city of Florence. Together we will visit the Baptistry and the Bell Tower of the Cathedral, the Town Hall and its Loggia and its piazza, the guilds’ chapel Orsanmichele, the Franciscan monastery of Santa Croce and the Dominican monasteries of San Marco and Santa Maria Novella.

In this journey across the city, we’ll experience the unfolding of art and history from the eighth to the fifteenth centuries. Together, these places add up to a vivid apprehension of how every element of civic, religious, and commercial life are brought into coherence in the design of medieval-Renaissance cities, fostering the ideas and affections that shaped medieval and Renaissance culture and society.

Day 6

The Place of Virtue and the Influences of Character

Seminar: Virtue and Public Practice

Drawing on the examples of Orvieto, Siena, and Florence, we will consider how the civic design and “built environments” of towns and cities–including their public art–may have influenced the dispositions toward virtue (and vice) in the citizenry of that earlier epoch. As points of reference, we can turn to Plato’s and Aristotle’s descriptions of the polis, and to the Inferno and Purgatorio for Dante’s exploration of the interplay between political life and moral condition.

Discussion: Fostering the Virtues in our own schools

For context, what do we see as the dispositions toward virtue and vice as fostered by the civic design and the use of the arts in the cities and towns of our own society?

How does the architecture, interior design, and decorative elements of our schools subtly encourage (or discourage) the virtues we wish to cultivate in our students?

In the Renaissance, public art was assumed to have educative value; no argument needed. How would you go about persuading parents, donors, board members, civic funding agencies, that (sometimes expensive) art has positive pedagogical and behavioral impact (or “value”)?

Day 7

Building on the Ruins (and Classical-Christian education)


After checking out of our convent in Orvieto we’ll travel to Rome where we’ll spend the final two days or our journey focusing on the repurposing of pagan classical temples and public buildings into places of Christian worship.

Excursion: Rome

As we arrive in the Eternal City, we’ll explore some of Christendom’s earliest churches, among them the vast Santa Maria Maggiore, constructed on the model of a Roman basilica, and the nearby diminutive churches dedicated to the martyred sister saints Pudenziana and Prassede; the Baths of Diocletian, in ruin and refurbished (with Michelangelo called in as the architect) as the Church of the Blessed Virgin Mary and all the Angels and Martyrs.

After lunch and checking into our hotel, we will visit the Pantheon–temple of all the gods re-dedicated as a church in honor of the panoply of Christian martyrs—and the adjacent church of Santa Maria built on the site of the temple to the goddess Minerva. Then to Piazza Navona, repurposed from the Roman sports stadium, with Bernini’s fountain of the Four Rivers and the jewel of a church honoring the young martyr Saint Agnes, stopping on the way to see Caravaggio’s masterpiece of the Calling of Matthew in the church of the French community.

Day 8

The Eternal City and the Contemporary Academy

Excursion: Day 2 Rome

This morning we’ll continue our discovery of the layers of Christian virtue through the centuries with a visit to the church of San Clemente, begun as a first-century house church in a convert’s villa near the Colosseum. From the 12th-century nave of the present-day church, we can descend into the underground layers of the church and the ancient neighborhood, excavated in the 19th century. Our morning will conclude with a visit to the Roman Forum and the church of Saints Cosmos and Damian. The afternoon is free for exploring Rome until our final Italian dinner and evening discussion.

Final Discussion:

In what circumstances can we re-purpose or re-dedicate the “temples” of our contemporary built environment into “schools of Christ” (in St. Benedict’s phrase)?

Day 9

Departure to FCO airport

After an early breakfast in our hotel we’ll say farewell to the Eternal City and head to the airport for a final goodbye and to catch our flight home.

Day 10

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Day 15
sample Itinerary
· Day 1  
Arrive in Rome, get settled into the Villa Lante, our beautiful convent residence. This afternoon we’ll stroll through the city visiting Santa Maria in Cosmedin, the Capitoline, and the Pantheon before celebrating our first night with a traditional Roman dinner.

· Day 2
This morning we’ll visit the Forum and Palatine, taking time to read excepts from Cicero, Plutarch, and Livy.

· Day 3
Today we’ll travel to Subiaco to visit the first Monastery of Saint Benedict. Returning to the city after lunch, we’ll stop to see Santa Costanza, Saint Agnese outside the walls, and the Catacombs of Priscilla.

· Day 4
This morning we’ll visit the Scavi of Saint Peters, tour the Basilica, then visit the Vatican Museum.

· Day 5
After breakfast this morning, we’ll depart for Pompeii, the ancient Roman city destroyed (and preserved) by the eruption of Vesuvius.  

· Day 6
Students who wish to attend Sunday services this morning may do so. In the later part of the day we’ll regroup to visit Saint Peter in Chains, San Clemente, and conclude the day with vespers.  

· Day 7
This morning we will visit the Borghese Gallery and make a tour of churches with the works of Caravaggio in Rome.

· Day 8
We’ll depart by train for Florence. After checking into our hotel, we’ll visit the central market for lunch, have a walking tour through Medieval and Renaissance Florence, and conclude with a visit to the Accademia and Michelangelo’s David.

· Day 9
This morning we’ll visit San Marco, visit the Baptistry and climb Bruneleschi’s dome. This afternoon we’ll be free to explore the city in small groups before regrouping for vespers in San Miniato.  

· Day 10
This morning we’ll visit the Uffizi Gallery followed by a free afternoon with small group visits to Dante’s house, the Bargello, and Santa Croce. This evening we’ll celebrate with a Tuscan feast.

· Day 11
Depart Florence, fly home.

12 Days In Turkey

· Istanbul, 3 days: Hagia Sophia, Hagai Irene, Chora, Patriarchate, underground cistern, Grand Bazaar, Topkapi Palace

· Cappadocia, 3 days: Gorem church, underground city and churches, open air monastery, Hittite Pottery lecture, and hot air balloon ride.

· Pergamon, 1 night: an ancient Roman city where Paul preached and one of the churches of Revelation.

· Sardis, stop only: One of the oldest synagogues, one of the churches of Revelation to whom it is written:  “If therefore thou shalt not watch, I will come on thee as a thief, and thou shalt not know what hour I will come upon thee.”

· Loadacia, (2 nights in Pamukkale): one of the churches of Revelation, to whom it is written: “I know thy works, that thou art neither cold nor hot: I would thou wert cold or hot.”

· Hierapolis: archeological site of the ancient city and the monument to the martyrdom of St. Phillip.

· Miletus: one of the stops on St. Paul’s third missionary journey.

· Ephesus, (3 nights Kusadisi): the Basilica of Saint John, Ephesus, House of Mary, and Basilica of Mary

· Tarsus, (possible extension): the birthplace of St. Paul, center of stoic philosophy, where paul trained at the gymnasium

· Antioch, (possible extension): the church of St. Peter (one of the oldest churches in the world), center of Paul’s missionary journeys, and first site where Christians took the name.


Guided by the image of the Incarnation, that “God was made flesh and dwelt among us” in order that we might become like Him, a pilgrimage is more than a trip to the places of the bible, to the sites of the early church, or to the homes of the saints, it is a journey that seeks to place the image of Christ in us that we might be made more like Him.


The antidote to consumer travel, the goal of pilgrimage is for travelers to stand as Moses before the burning bush, to be transformed, and to have their own lives taken up and changed by the spiritual realities they seek.

Each day will incorporate suggested readings from scripture and the writings of the early church, time for private or shared reflection and prayer, and meals that celebrate the joy of God in neighbor.

A prayerful understanding of place

For Christians, place is never just the created, natural order, nor is it pure, spiritual reality, it must always be both. A pilgrimage encounter with place must both seek God in place, in the finite and particular, through the lives and examples of the Saints and it must require travelers to take those footsteps themselves, each traveler must seek to move through place to God. From this perspective, pilgrimage is an image of prayer, it seeks to turn the body, the footsteps, the act of every traveler into the image of prayer.


The modern country is the geographic center of many of the events of the bible and early church. It is in in Turkey that Abraham circumcised Isaac, that Jacob wrestled the angel, that Paul and Peter founded the church of Antioch, that Byzantine Christianity thrived for more than thousand years, and to this day it is the home of the Armenian Apostolic tradition, the Assyrian church, and it is the only county where Aramaic, the language of Christ, is still spoken.


To challenge the apathy and aimlessness of our current cultural moment with mental discipline and rigorous training.


• Early morning workouts
• Rucking
• Pre-dawn Mount Kerkis hike
• Hike to Cave of Pythagoras
• Underwater rock hauling
• Megalo Seitani hike
• Ice baths
• Roasted lamb or goat on a spit
• Big meals with an abundance of food, roasted meats, wine, toasts, and a spirit of fellowship and conviviality
• Camaraderie, contemplation, and conversation
• Open-water swims and spearfishing (optional)


SQ4 coaches men to achieve a higher level of fitness and athletic excellence by blending the principles of ancient philosophy with the empirical depth of modern exercise science designed to permanently enhance their life, mindset, habits, and physique.


The key to a lasting fitness transformation is understanding the layered nature of man.  The SQ4 methodology is based on the ancient understanding of man and virtue that transcends cultures and epochs:

• Psyche – Life – Courage
• Nous – Mindset – Wisdom
• Pneuma – Habits – Temperance
• Soma – Physique – Justice


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• Daily pilates
• Biking the trans humana ancient shepherd paths
• Cooking lesson
• Winery and Olive Oil visits
• Castel del Monte of Frederick II
• Visits to locals towns
• Relaxing evenings of wine, food, and a spirit of celebration
• Practicing keeping the body young with age
• Meeting with local pottersSpa and self-care


More than a trip to Italy, this weeklong travel-retreat will focus on being healthy physically and mentally through activities that nourish and rejuvenate. Whether detoxing from cell phones, work, or other daily demands, this is an opportunity to be in the moment, to enjoy delicious Italian food, wine, and the fresh perspectives provided by a stunning Italian landscape.


Self care doesn’t just mean pampering, it means intentionality. Pilates trains your body to make intelligent movements that support your body all day, every day. Travel encourages a perspective of vulnerability, of stepping into the new and beautiful in order to rediscover the new and beautiful within yourself. From this perspective, an experience of the ‘importance of place’ in Puglia is equally to realize that connectedness within yourself.


All breakfasts, 1 lunch, and 7 dinners
Bus or high-speed train transportation between activities, sites, and cities
8 nights in historic lodging run by nuns
Entrances and local guides to more than 10 different sites
Your friendly Alithea tour manager for the duration of the tour.
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For further questions don't hesitate to reach out to us directly.



Pack Light

Alithea hotels are boutique, family-run and centrally located in the historic centers where the ancient roads are too small for buses. That often means needing to walk between our bus and hotels. Between destinations we will be required to carry our own luggage which may include significant stairs and no elevator. We encourage our travelers to take a simple carry-on size bag with a small backpack for outings.

Come Prepared

Alithea tours are outrageously fun. Come prepared to live in the moment. We will walk, talk, celebrate, dine, and make beautiful discoveries together. When we’re not exploring with our local guide we’ll be encouraged to venture out on our own, to celebrate our discoveries with a glass of wine, or simply to relax and take in the beautiful views. Of course, we can’t visit ancient and beautiful sites without getting there first, and sometimes that means significant walking. There will be several days on this tour that will be physically demanding due to the amount of walking. Please contact us if you have questions or concerns before booking.

Bus and Travel Time

On our excursions out of Orvieto we will take the bus. We’ll not only use this time to relax and enjoy the view, but to further discuss topics from the seminars.


For further questions don't hesitate to reach out to us directly.

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Reserve Your Place

Teaching a Classical Education

A $500 deposit is required to reserve your spot. All deposits and discounts (if applicable) will be applied to the total tour price. Deposits are refundable within 30 days of payment.

*Read our refund policy here
A Christian Classical Approach to Travel
Travel encourages a living experience of art, history, and ideas that transforms the classroom into an immersive experience of truth, beauty, and goodness. Museums, meals, archeological sites, and foreign languages are not merely artifacts that help students consider the world, they cultivate a love of wonder, moral imagination, and a rich understanding of the truth. More than a student trip, travel is an invitation to become a lifelong practitioner of the loves that shape the soul.
The Prayerful Traditions of Europe
Rather than treating churches and monasteries as defunct historical monuments, Alithea and Oakdale Academy invite students to approach them as places of prayer and worship