Uncharted Worlds: Perspective-Shifting Journeys with Crooked Compass

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Curiosity changes everything. That’s the thread running through our conversation with Crooked Compass founder and CEO Lisa Pagotto, whose frontier-travel philosophy favors depth over dazzle and local impact over checklists. In this second episode of our Emerging Multi-Day Tour Operators series, we explore how she designs perspective-shifting journeys in safe yet overlooked destinations — from Papua New Guinea’s highland festivals and WWII relics to Mongolia’s sweeping steppe — and why honesty about difficulty, logistics, and culture leads to more meaningful travel.

Lisa reveals the craft behind the brand: small-group tours capped at 12, a post-pandemic rise in private touring, and a rigorous duty of care that comes before any itinerary is built. For her, sustainability isn’t about box-ticking — it’s about keeping money in local communities and creating genuine cultural exchange. We also look at who’s booking these trips: often 55-plus, well-traveled, with a growing solo-female segment seeking connection, storytelling, and transformation.

We chart what’s next in frontier travel — from the Balkans and the Silk Road’s five Stans to North Africa’s unsung gems like Tunisia and Algeria. Lisa also shares how she evaluates post-conflict destinations such as Iraq or Syria through careful risk frameworks, and why transparent pre-trip education turns hesitation into confidence. Along the way, a remarkable field story from North Korea challenges perceptions and captures the true spirit of perspective-shifting travel.

Come for the inspiration, stay for the playbook — how to spot emerging destinations, build local partnerships, and choose journeys that make a difference. Learn more at crooked-compass.com.

👉 Listen to Uncharted Worlds: Perspective-Shifting Journeys with Crooked Compass Now

🔥 Special Thanks to our Season 6 Title Sponsors for their Support: Holafly, Propellic, PayCompass, Kaptio, Civitatis and WeRoad

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