Zachary Smith of Anywhere: Stress-Free Travel, Local Experts & The Future of Personalized Journeys

About this episode

Zachary Smith discusses how Anywhere is transforming travel planning into a stress-free and personalized experience.

Special Offer Get $100 off your first trip with Anywhere by signing up here: anywhere.com/thelayover 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…

People in this episode

Guest: Zachary Smith

Topics covered

• stress-free travel
• personalized journeys
• local experts
• cultural immersion
• travel planning

Keywords

• travel
• Anywhere
• personalized itineraries
• local experts
• cultural experiences

Sponsors

Anywhere

Mentioned in this episode

Organizations: Anywhere

Places: Oaxaca, Costa Rica, Cuba, Mexico, Japan

More episodes of The Layover

• Inside Hospitality’s Human Future with Sander Allegro: High Tech, High Touch & the Power of Experience · June 4, 2026 · 54 min
• Inside GuestOS with Jessie Fischer: AI Hospitality, Yosemite & the Future of Guest Experience · May 15, 2026 · 54 min
• Building Pink Notebook: Goedele Mangelaars on the Future of Travel Tech · April 30, 2026 · 37 min
• Inside LOST iN with Jon Skogmo: Print Revival, IRL Experiences & The Future of Travel Media · April 23, 2026 · 26 min
• Inside the Las Vegas Aces with D’Andra Duggans: Sports Travel, Brand Experience & Building a Championship City · February 19, 2026 · 11 min
• Inside Black Tomato with Tom Marchant: Transformational Travel, Human Connection & the Future of Luxury · February 10, 2026 · 1h 2m