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In this episode of The Layover, we sit down with Zachary Smith, CEO of Anywhere, to unpack how a one-way trip to Oaxaca and an unexpected detour in Costa Rica grew into a global travel company redefining what it means to plan (and actually enjoy) your trip.

Born from the simple idea of making travel less stressful, Anywhere blends technology with human connection, relying on local experts in every destination to design personalized, culturally immersive itineraries that put peace of mind first.

Zach shares how Anywhere is:

- Eliminating “tyranny of choice” overwhelm with curated, human-guided planning

- Pairing travelers with local experts who understand the culture—and can step in if things go wrong

-Turning stress into serenity through a “connected trip” model that flexes in real time

- Focusing on authenticity over algorithms: no tour buses, no buffet lines, just real-world experiences

- Scaling from Costa Rica to Cuba, Mexico, Japan, and beyond while staying deeply human-centric

- Building a brand rooted in accountability, trust, and transformative travel

- Whether you’re a busy parent dreading logistics, a cultural explorer craving authenticity, or someone who wants to make travel feel less like work and more like discovery, this episode reveals how Anywhere is rewriting the playbook for stress-free, meaningful journeys.