Introduction: The Art of Power and Pragmatism

Niccolò Machiavelli’s journey from disgraced statesman to immortal philosopher teaches leaders how to navigate chaos, wield influence, and craft legacies that transcend failure. Exiled after the Medici’s return in 1512, he transformed despair into The Prince and Discourses, redefining leadership as the interplay of cunning, adaptability, and moral flexibility. This three-day tour traces his footsteps through Florence’s political heart, blending history, philosophy, and introspection to help you master the strategic storytelling of your own leadership journey.

Timeline

Day	Hero’s Journey Stage	Theme	Locations
Day 1
9:00 AM	Call to Adventure	The Spark of Ambition	Palazzo Vecchio (seat of Florentine power)
11:00 AM	Refusal of the Call	Exile and Despair	Machiavelli’s Exile Villa (San Casciano, symbolic reflection in Florence)
2:00 PM	Crossing the Threshold	Embracing the Unorthodox	Bargello Museum (power symbols)
Day 2
9:00 AM	Tests, Allies, Enemies	Navigating Chaos	Medici Chapels (rivalry and patronage)
11:00 AM	Approach the Cave	Confronting Crisis	Santa Croce Basilica (tombs of mentors/rivals)
2:00 PM	Transformation	Writing the Future	Laurentian Library (intellectual rebirth)
Day 3
9:00 AM	Apotheosis	The Philosopher’s Legacy	Orti Oricellari Gardens (intellectual debates)
11:00 AM	Return with Wisdom	The Eternal Strategist	Ponte Vecchio (symbol of resilience)
2:00 PM	Resurrection	Immortality Through Ideas	Santa Croce Basilica (Machiavelli’s tomb)

Day 1: Call to Adventure

Location: Palazzo Vecchio (Machiavelli’s workplace as Second Chancellor)
Hero’s Journey Stage :
Machiavelli’s call came in 1498 when the Florentine Republic appointed him Second Chancellor. At Palazzo Vecchio, he negotiated with Cesare Borgia and Louis XII, learning that power lies in perception. His diplomatic missions—documented in Legations—reveal how leaders must balance idealism with realpolitik.
Reflection: What “diplomatic mission” (challenge) defines your leadership origin story?
Question: How do you navigate the tension between morality and pragmatism in your decisions?

Day 1: Refusal of the Call

Location: Villa at San Casciano (symbolized through Florence’s exile sites)
Hero’s Journey Stage :
After the Medici’s 1512 return, Machiavelli was tortured, exiled, and stripped of power. His refusal was despair—until he channeled it into writing. At his villa (symbolized here), he traded statecraft for philosophy, penning The Prince to prove resilience outlives defeat.
Reflection: What “exile” (setback) could become your creative catalyst?
Question: How can you transform powerlessness into intellectual reinvention?

Day 1: Crossing the Threshold

Location: Bargello Museum (symbols of Medici authority)
Hero’s Journey Stage :
Machiavelli’s threshold was accepting that virtù (prowess) matters more than virtue. The Bargello’s Medici relics—coats of arms, swords—mirror his lesson: leaders must master both force and persuasion. His Art of War (1521) reimagined military strategy as civic duty.
Reflection: What unorthodox tool could redefine your leadership?
Question: How do you balance fear and love in your team’s loyalty?

Day 2: Tests, Allies, Enemies

Location: Medici Chapels (power dynamics)
Hero’s Journey Stage :
Machiavelli’s tests included surviving Medici suspicions while seeking patronage. The Chapels, built to legitimize Medici rule, reflect his insight: alliances are temporary, but influence is eternal. His dedication of The Prince to Lorenzo de’ Medici was a gamble to regain power.
Reflection: Which “Medici” (rival/ally) tests your strategic patience?
Question: When should you appease versus confront those in power?

Day 2: Approach the Cave

Location: Santa Croce Basilica (tombs of mentors/rivals)
Hero’s Journey Stage :
The cave was Machiavelli’s 1520s struggle to write Florentine Histories under Medici censorship. At Santa Croce, Dante’s empty tomb (he was exiled) mirrors Machiavelli’s fight to tell truth to power. Leaders learn that legacy demands courage to document hard truths.
Reflection: What uncomfortable truth must your leadership confront?
Question: How do you preserve integrity while navigating political constraints?

Day 2: Transformation

Location: Laurentian Library (intellectual rebirth)
Hero’s Journey Stage :
Machiavelli’s transformation came through synthesizing history and philosophy. The Laurentian Library, designed by Michelangelo, symbolizes his belief that knowledge is power. His Discourses on Livy argued that republics thrive on conflict—a lesson for modern teams.
Reflection: What historical lesson could revolutionize your leadership?
Question: How do you institutionalize constructive dissent in your organization?

Day 3: Apotheosis

Location: Orti Oricellari Gardens (debate hub)
Hero’s Journey Stage :
Machiavelli’s apotheosis was becoming a philosopher-mentor. In these gardens, he debated with Florence’s elite, arguing that leadership is performance. His play Mandragola (1518) satirized power’s corrupting allure, teaching that humor disarms tyranny.
Reflection: What “role” do you play to inspire your team?
Question: How can satire or storytelling reveal uncomfortable truths?

Day 3: Return with Wisdom

Location: Ponte Vecchio (resilience symbol)
Hero’s Journey Stage :
Machiavelli’s return was posthumous: his works outlived him. The Ponte Vecchio, rebuilt after floods, embodies his lesson that adaptability ensures survival. Leaders learn that flow comes from embracing chaos as raw material.
Reflection: What “bridge” must you build to connect vision to reality?
Question: How does your leadership thrive in uncertainty?

Day 3: Resurrection

Location: Santa Croce Basilica (Machiavelli’s tomb)
Hero’s Journey Stage :
The resurrection is Machiavelli’s eternal influence. His tomb, inscribed “Tanto nomini nullum par elogium” (“No eulogy matches this name”), teaches that legends are written by the bold. Leaders learn that immortality lies in reshaping paradigms.
Reflection: How will your leadership alter history’s trajectory?
Question: What “Prince”-like treatise will define your legacy?

Conclusion: The Leader’s Gambit

Machiavelli’s Hero’s Journey reveals:

1. Crisis is opportunity (exile → intellectual rebirth).
2. Virtù trumps virtue (pragmatism over idealism).
3. Legends outlive lives (ideas conquer mortality).

Final Questions:

1. Palazzo Vecchio: What “Borgia-like” challenge demands your strategic cunning?
2. Orti Oricellari: How do you mentor others to question power structures?
3. Santa Croce: What epitaph will your leadership deserve?

“The wise man does what the times demand.” —Machiavelli’s Discourses, III.9.

Tour Details:

• Duration: 3 days
• Start Time: 09:30 AM
• End Time: 10:00 PM
• Cost: € 2.250 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.