The Layover

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 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.

In this episode of The Layover, we sit down with Einar Garzoa, co-founder and CEO of Conserve Safari, to explore how a finance career in Europe transformed into a mission-driven journey in Africa’s wilderness. From Latvia to Uganda to Tanzania, Einar’s story is one of reinvention—trading spreadsheets for savannahs to build eco-conscious safari lodges that connect travelers with nature and purpose.Conserve Safari isn’t just about game drives and luxury tents. It’s about creating spaces where travelers can rediscover themselves while supporting conservation and local communities.Einar shares how Conserve Safari is:Building sustainable safari lodges that bring comfort without cutting travelers off from the wildTurning conservation into a financially viable model that funds national parks and anti-poaching effortsTraining staff and educating guests to be stewards of nature long after they leave campDesigning transformational experiences that help travelers look inward, not just outwardExpanding into wellness-focused safaris that blend yoga, mindfulness, and immersion in African landscapesEnvisioning 35 eco-lodges across East Africa to scale both conservation and community impactWhether you’re an ecotourist, an adventurer seeking meaning, or simply curious about how travel can transform lives, this episode offers a rare look at how safaris can be more than sightseeing, they can be soul-searching.

In this episode of The Layover, we sit down with Ian Prichard, CEO and co-founder of Black Tie Ski Rentals & Delivery, to explore how a small-town idea sparked by an Alan Jackson VIP fitting turned into North America’s leading ski and bike delivery network.From maxing out credit cards to launch a two-van operation in Steamboat Springs, to growing into 20 licensed locations across the U.S. and Canada, Black Tie has rewritten the ski rental experience—making it less about lines and logistics and more about lifestyle and leisure.Ian unpacks how Black Tie is:Turning the most dreaded part of skiing—rentals—into a concierge-level, in-room experienceBalancing affordability with luxury, proving “black tie” doesn’t have to mean overpricedExpanding into summer with bike rentals, giving operators year-round sustainabilityScaling through a unique licensing model that empowers local entrepreneursBuilding authentic community relationships with resorts, hotels, and conciergesKeeping customer service at the core—hiring personalities first, ski techs secondWhether you’re a skier, a snowboarder, or just curious about how hospitality meets entrepreneurship on the slopes, this episode offers a behind-the-scenes look at how Black Tie is blending high-touch service with smart growth to change the way we gear up for adventure.

In this episode of The Layover, we sit down with Michael Shiwdin, Group Vice President of Guest Engagement, Loyalty, and Strategic Partnerships at Wyndham Hotels & Resorts, to explore how the brand behind 24 hotel names is transforming travel rewards into something far more experiential and emotional.From turning points into Applebee’s and Panera Bread perks, to launching exclusive VIP auctions with the NFL, Wyndham is rewriting the playbook for loyalty—and it’s not just about free nights anymore.Michael unpacks how Wyndham is:Making loyalty programs more flexible, fun, and family-friendlyTapping into partnerships that meet travelers where they already live, dine, and playPrioritizing “memory-making” over pure redemption valueBuilding a program that speaks to value-conscious families, Gen Z adventurers, and road-trip superfans alikeCreating an ecosystem where points mean more than transactions—they mean storiesWhether you're a travel nerd, loyalty junkie, or just curious about what’s next in hospitality, this episode offers a front-row seat to how Wyndham is making travel feel more personal, playful, and accessible than ever.

In this episode, we journey into the sacred, the obscure, and the nearly forgotten with Eliot Stein, senior journalist and editor at the BBC, and author of the powerful new book Custodians of Wonder: Ancient Customs, Profound Traditions, and the Last People Keeping Them Alive. Eliot takes us behind the scenes of a decade-long reporting journey—one that led him across five continents in search of the final practitioners of ancient rites, endangered crafts, and cultural expressions on the edge of extinction. From the last Inca bridge master to the only family that still plays Mali’s 700-year-old royal instrument, Eliot explores how humanity’s most fragile traditions are preserved, passed down, or lost in a rapidly modernizing world. In this conversation, we explore: How Eliot gains trust and access in deeply private and remote communities The tension between storytelling and overexposure in the age of social media Why the disappearance of local culture, language, and ritual is a global extinction event What it really means to travel with curiosity, humility, and empathy Why “yes” is the most powerful word a traveler can carry Whether you're a cultural anthropologist at heart or a curious traveler wondering what’s being lost in our globally connected world, this episode offers a profound look at the quieter, endangered side of travel—and the people who keep wonder alive. And be sure to check out his book Custodians of Wonder, which can be found on his website https://www.eliotstein.me/

What does it take to turn a beloved local destination into a multi-platform media powerhouse? In this episode of The Layover, we sit down with Brian Bossuyt, Executive Vice President and CMO of the Pocono Mountains Visitors Bureau, to explore how his team is redefining destination marketing—one camera, one app, and one fall foliage map at a time.Brian shares how the Pocono Mountains region is:Attracting new and returning visitors year-round, from family road-trippers to luxury travelersLeveraging data, storytelling, and even its own 24/7 television network to inform, inspire, and convert audiencesBuilding strong partnerships with state agencies and local businesses to elevate small-town tourismNavigating trends like short booking windows, user-generated content, and travel inspiration via OTT and appsMaking travel more accessible, from multi-generational family reunions to last-minute escapesWhether you're a tourism professional, a media strategist, or a weekend warrior looking for your next trip, this episode offers a masterclass in modern travel marketing—and why the Poconos are having a serious moment.

In this episode, we sit down with Sebastian Schoepe, CEO of EagleRider, to explore how the iconic motorcycle travel company is steering the future of experiential travel. From reshaping the traditional rental model to embracing digital tools and immersive branding, Sebastian offers a candid look at how EagleRider is reaching younger, more diverse, and global audiences.

In this episode of The Layover, host and EVP of Partnerships at LOST iN, Dylan Conroy, hits the slopes with Dan Sherman, Chief Marketing Officer at Ski.com — the leading platform for planning and booking unforgettable mountain getaways.Together, they carve through the evolution of ski travel, unpack how data, content, and community are transforming the way people discover and experience winter destinations, and explore the challenges of marketing adventure in a rapidly changing digital landscape. Dan shares the behind-the-scenes strategy that keeps Ski.com at the forefront of mountain tourism and offers a glimpse into the future of alpine experiences — from personalized itineraries to sustainable snow sports.Whether you’re a seasoned skier or an armchair adventurer, this episode offers a fresh look at the culture, business, and passion driving the snow travel industry.