Uncharted Worlds: Perspective-Shifting Journeys with Crooked Compass

Oct 29, 2025

In this engaging discussion, Lisa Pagotto, founder and CEO of Crooked Compass, shares her passion for frontier travel, emphasizing authentic cultural experiences over typical tourist routes. She reveals how her small-group tours take travelers to unique destinations like Papua New Guinea and Mongolia while ensuring local communities benefit. Lisa discusses the shift towards private tours post-pandemic and highlights the growing number of solo female travelers seeking transformative journeys. Her insights on sustainability and safety in post-conflict areas offer a fresh perspective on responsible travel.

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INSIGHT

Frontier Travel Focus

Crooked Compass focuses on frontier travel to lesser-known, culturally rich destinations that mainstream operators overlook.
They run small-group tours (max 12) and private tours to deliver deep, perspective-shifting experiences.

ANECDOTE

Papua New Guinea's Diverse Faces

Papua New Guinea offers wildly different experiences across its 22 provinces from WWII relics to highland festivals and initiation ceremonies.
Lisa warns it's not for first-timers and highlights its raw, untouched appeal.

ADVICE

Do Firsthand Product Development

Build and sell frontier tours only after firsthand research and product testing with trusted local partners.
Walk the walk: don't offer experiences you haven't personally done or vetted.

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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

The #1 B2B Travel Podcast Globally. Over 100 Episodes. Listeners in 125 countries. New Episodes Every Weds.

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