Italian Road Trip Itinerary
Overview of our Quest for Castles through Italy
Campaign 1
October 29–November 5, 2025
GENOA
October 29–31, 2025
PIEDMONT
October 31–November 2
3 property tours
DAMANHUR
November 2–5
3 nights at artistic community
Full moon ceremony
Commemoration of the Dead ceremony
Campaign 2
November 5–12, 2025
MILAN
November 5–6
• Opening Dinner
LAGO DI GARDA
November 6–10
• Lago Iseo
• 3 Properties
FLORENCE
November 10–12
• Tertulia Community
Campaign 3
November 12–19, 2025
LAGO TRASIMENO
Key property stay and assessment
Opening & closing dinner
Nearby property tours
Castiglione de Lago
Hot springs day trip
Beach & biking trips
Interactive Road Trip Map
Explore the Castle Quest road map for Italy…. a curated tour of historic properties, intentional communities and cultural sites (oh, and hot springs)
Join us in Italy!
Over the course of three weeks, we’ll visit intentional communities, tour large properties, and talk honestly about what works (and what doesn’t) when people set out to build community. We’ll share our learnings along the way to help inspire others to create their own community strongholds.
The trip is split into three Quest Campaigns. The first two are more mobile — we’ll be on the road, meeting people, and learning from communities who’ve already figured out their own models of regenerative living. We’ll finish with a week at a property near Lago Trasimeno in Umbria that we think could be the right place for a creative wellness community. Together, we’ll walk the grounds, visit nearby sites, share meals, and ask the real questions: Does this place feel like home? And if it does, are we ready to make it ours?
Campaign #1:
Oct 29 – Nov 5, 2025
Genoa
Piedmont Region
Milan, Italy
(5 seats available)
Campaign #2:
Nov 5 – Nov 12, 2025
Milan
Lake Region
Florence, Italy
(5 seats available)
How it works
Apply to join the Quest
Join our WhatsApp group (link shared after application)
Secure your spot!
Deposit: $500. Seats allocated on a first-come basis
Estimated cost: $1,250 per week/campaign
Refund policy: Fully refundable until Oct 10, 2025. 50% refundable until Oct 20, 2025.
What’s included
A week-long adventure with a curated small group
Opening campaign dinner
Property/community visits
Cultural excursions & historic sites (entrance fees not included)
7 nights accommodations (shared & private options)
Van seat + fuel
Options:
Add a partner to same room/bed at a reduced cost
Book your own travel and/or accommodations
Who we are calling in
Fellow Questers may be…
Drawn to the idea of creating or living in intentional communities
Interested in relocating to Europe and exploring new ways of life
Curious about the potential of investing in co-living communities
Fascinated by history and how heritage properties can be reimagined for modern community living
You’re invited to join us — to learn, connect, and explore what it takes to bring these visions to life.
Lago Trasimeno Estate
Our journey will culminate at a 16,684 sq ft estate set on over 376,000 sq ft of land near Lago Trasimeno, Umbria. This property is already designed for mixed-use living and hospitality — making it a promising foundation for a creative, wellness, and innovation-focused community.
The estate includes 500 mature olive trees that produce high-quality oil, creating opportunities for sustainable farming and farm-to-table living. Its grounds feature a 20-unit village of private apartments alongside a 6-bedroom Tuscan villa with its own pool deck and panoramic views. Just minutes away lies Lake Trasimeno, Italy’s fourth-largest lake, surrounded by villages, vineyards, and beaches — adding year-round cultural and economic value. Together, these elements make the estate a strong foundation for an international community rooted in creativity, wellness, and authentic Italian living.
Highlights include:
60 total rooms, including 28 bedrooms, 19 kitchens, and 12 living rooms
2 swimming pools with panoramic countryside views
A restaurant, already fully equipped and locally staffed
Improvements include converting a 15-car garage into a co-working and innovation hub + rooftop event space
Situated minutes from Lake Trasimeno, one of Italy’s most enchanting regions
15 min to the nearest train station – 2 hours to Florence, 4 hours to Rome
The co-investment path
If the Lago Trasimeno property meets our criteria, we will officially open the collective investment cycle on Nov 15. Our goal is to purchase outright (no banks, no loans) and immediately begin developing our Creative Wellness Community that blends:
Co-living & secondary residences
Visa/residency support (Golden Visa, work visas, digital nomad programs)
On-site wellness amenities, culture, and hospitality
Sustainable shared resources and regenerative practices
Expected returns:
20–30% ROI over 3–5 years, with real impact and a vibrant international community as your dividend.
Meet the CQ Guild
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Jordan Hammond
FOUNDER
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Malena Grosz
PROJECT MANAGER
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Julie Ghannam
MARKETING / DESIGN
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Ian Briggs
IMMIGRATION ADVISOR
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Thea Logan
ADVISOR
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Josh Burtnett
INVESTMENT ADVISOR
Let’s Connect
Send us a note to introduce yourself and ask anything you’re curious about. Got some special skills or referrals you’d like to share? Tell us about it!