Introduction: The Leader’s Inferno
Dante Alighieri’s exile from Florence in 1302 transformed him from a disgraced politician into the architect of Western literature’s greatest journey. His Divine Comedy teaches leaders how to navigate crisis, confront their shadows, and emerge with clarity. In this tour Peter de Kuster uses The Hero’s Journey story model to explore Dante’s Florence, where every street and stone whispers lessons about resilience, ethics, and the stories we tell ourselves.
Key Lessons:
- Exile as Catalyst: How rejection can fuel reinvention.
- The Power of Guides: Virgil’s mentorship as a model for collaborative leadership.
- Confronting Shadows: Dante’s journey through Hell as a blueprint for self-awareness.
Timeline Overview
| Day | Hero’s Journey Stage | Theme | Locations |
|---|---|---|---|
| 1 | Call to Adventure | Crisis and Awakening | Baptistery, Piazza della Signoria |
| 2 | Crossing the Threshold | Exile and Resilience | Dante’s House, Santa Croce |
| 3 | Tests, Allies, Enemies | Mentorship and Ethics | Bargello Museum, Church of Santa Margherita |
| 4 | Transformation | Confronting Shadows | Florence Cathedral, Giotto’s Bell Tower |
| 5 | Return with Wisdom | Legacy and Redemption | Uffizi Gallery, Arno River |
Day 1: Call to Adventure (Ordinary World → Crisis)
Theme: Crisis as Awakening
Locations:
- Baptistery of San Giovanni: Where Dante was baptized and first envisioned Beatrice, symbolizing innocence and inspiration.
- Piazza della Signoria: Site of political upheaval where Dante served as prior before exile.
Hero’s Journey Stage (200 words):
Every hero’s journey begins with a rupture. Dante’s Inferno opens in a “dark wood” of midlife crisis—a metaphor for leadership crossroads. In 1300, as prior of Florence, Dante’s political idealism clashed with corruption, leading to exile. The Baptistery, where his spiritual journey began, mirrors the Ordinary World before crisis strikes.
Reflection:
- Innocent Archetype: What ideals defined your early leadership?
- Orphan Archetype: What loss or failure reshaped your path?
Question:
Dante’s love for Beatrice began here. What or who inspires your leadership “divine vision”?
Day 2: Crossing the Threshold (Exile → Resilience)
Theme: Embracing the Unknown
Locations:
- Dante’s House Museum: Explore artifacts of his exile and early works (La Vita Nuova).
- Santa Croce: Tomb of Dante (empty—Florence’s belated apology for banishing him).
Hero’s Journey Stage (200 words):
Exile forces heroes to confront their limits. After 1302, Dante wandered Italy, writing De Monarchia and Commedia. Santa Croce’s empty tomb symbolizes Florence’s regret and Dante’s Threshold Crossing—transforming rejection into creative fuel.
Reflection:
- Warrior Archetype: What battle (internal/external) defines your leadership?
- Caregiver Archetype: How has serving others sustained you in crisis?
Question:
Dante wrote Commedia to “heal the world.” What legacy project could redeem your struggles?
Day 3: Tests, Allies, Enemies (Mentorship → Ethics)
Theme: Guides and Moral Courage
Locations:
- Bargello Museum: See Giotto’s fresco of Dante and the Church of Santa Margherita (Beatrice’s family church).
- Via del Corso: Walk the street where Dante first met Beatrice.
Hero’s Journey Stage (200 words):
Dante’s guides—Virgil, Beatrice, St. Bernard—symbolize reason, love, and faith. The Bargello’s frescoes depict Florence’s political factions, the Tests and Allies that shaped Dante’s ethics. His mentor Brunetto Latri (condemned in Inferno) warns against moral compromise.
Reflection:
- Mentor Archetype: Who has guided you through “dark woods”?
- Destroyer Archetype: What outdated systems must you dismantle?
Question:
Dante placed corrupt leaders in Hell’s deepest circles. What ethical lines will you never cross?
Day 4: Transformation (Hell → Self-Awareness)
Theme: Confronting Shadows
Locations:
- Florence Cathedral: Climb Brunelleschi’s dome for a “view from Paradise.”
- Giotto’s Bell Tower: Reflect on art’s role in societal transformation.
Hero’s Journey Stage (200 words):
Dante’s journey through Hell (Inferno) forces him to confront greed, pride, and betrayal—sins that destroy leaders. The cathedral’s height mirrors the Ordeal of self-reckoning. Like Dante, leaders must ask: What shadows lurk in my soul?
Reflection:
- Lover Archetype: What do you love enough to endure Hell for?
- Creator Archetype: How can art or storytelling heal your team?
Question:
Dante meets Ulysses in Hell for reckless ambition. When has your ambition helped or harmed others?
Day 5: Return with Wisdom (Legacy → Redemption)
Theme: Crafting Eternal Impact
Locations:
- Uffizi Gallery: Study Botticelli’s Map of Hell and Dante’s influence on Renaissance art.
- Arno River: Walk the banks where Dante found inspiration.
Hero’s Journey Stage (200 words):
Dante’s Return is not physical but spiritual. His Commedia redefined literature, proving exile’s creative potential. The Uffizi’s art shows how crisis births legacy.
Reflection:
- Ruler Archetype: How will you steward power differently post-journey?
- Sage Archetype: What wisdom will guide your next chapter?
Question:
Dante’s final line—“the love that moves the sun and stars”—embraces divine order. How can your leadership align with a higher purpose?
Conclusion: The Leader’s Paradiso
Dante’s journey teaches that great leadership is born in crisis, refined by exile, and redeemed through storytelling. Like Michelangelo (who drew inspiration from Dante), he turned pain into flow by telling a story of divine love.
Final Questions:
- Baptistery: What “dark wood” are you navigating, and how can it redefine your purpose?
- Santa Croce: What empty tomb (regret or unfulfilled promise) motivates your legacy?
- Uffizi: How will your leadership inspire art, innovation, or justice?
Lessons from Dante’s Hero’s Journey
- Exile as Innovation: Crisis forces creativity.
- Ethics Over Expediency: Hell awaits leaders who betray their values.
- Storytelling as Legacy: “The love that moves the sun and stars” begins with the story you tell yourself.
“Lasciate ogni speranza, voi ch’entrate” (Abandon hope, all ye who enter) applies only to those who refuse to journey.
Tour Details:
- Duration: 5 days
- Start Time: 09:30 AM
- End Time: 10:00 PM
- Cost: € 3.450 per person excluding VAT per person and excluding hotel accomodation
You can book this tour by sending Peter an email with details at peter@wearesomeone.nl
Your Tour Guide
Peter de Kuster is the founder of The Heroine’s Journey & Hero’s Journey project, a storytelling firm which helps creative professionals to create careers and lives based on whatever story is most integral to their lives and careers (values, traits, skills and experiences). Peter’s approach combines in-depth storytelling and marketing expertise, and for over 20 years clients have found it effective with a wide range of creative business issues.

Peter is writer of the series The Heroine’s Journey and Hero’s Journey books, he has an MBA in Marketing, MBA in Financial Economics and graduated at university in Sociology and Communication Sciences.