Tom unpacks how Black Tomato has helped pioneer the rise of transformational travel, creating trips that prioritize how travelers want to feel, not just where they want to go.

In this conversation, Tom explores:

• Why luxury today is defined by thoughtfulness, access, and emotion, not just five-star amenities
• How Black Tomato finds meaningful experiences beyond overtouristed destinations
• The role of local fixers and human relationships in creating truly personal journeys
• Designing family and multi-generational travel that brings people together—without friction
• Why AI can support travel planning but will never replace human intuition and trust

Whether you’re fascinated by the psychology of travel, seeking deeper experiences beyond the bucket list, or curious how luxury brands stay human in an AI-driven world, this episode offers a thoughtful look at why the most powerful journeys don’t just change where you go—they change how you see the world.

🌍 Discover more about Black Tomato and their approach to transformational travel at blacktomato.com.

• Website: https://www.blacktomato.com/
• Instagram: @blacktomatotravel
• Tom Marchant on Instagram: @tommymarchant10
• Gift of Boredom (mentioned in conversation)

Destinations and itineraries mentioned:

• Iceland: Snorkel and dive between tectonic plates
• A Journey into Mongolia (for campfire cookouts, eagle hunting, and mountain monasteries)
• Ultimate Bhutan: A Luxurious & Cultural Retreat (spiritually enlightening and as remote as they come)
• An Adventure Across Iceland (for magma chambers, trolls, and geothermal tomato farms)
• Switzerland & Italy (a luxury vacation in the Alps, lakes, and coast)
• An insiders guide to the Amalfi Coast: Limoncello, sweeping vistas and storied villas

From navigating brand partnerships and audience growth to balancing creativity with commercial realities, Mike and Erica share an insider’s perspective on building a media platform rooted in authenticity, intention, and community.

Together, they explore:

• How Unplugged Collective approaches travel storytelling with purpose, not just reach
• Why depth, perspective, and credibility matter more than ever in a crowded media landscape
• What brands misunderstand about creator partnerships—and how to get them right
• How audience trust is built through consistent point of view and lived experience
• Where travel media is headed as platforms, formats, and consumer behavior continue to shift

Whether you’re a creator, brand marketer, tourism board, or simply passionate about thoughtful travel, this episode offers a grounded look at how Unplugged Collective is shaping the future of travel media—one story at a time.

Ever wonder what a city is like beyond the tourist traps? LOST iN is a travel company built on curiosity...dedicated to the food, fashion, people, and stories that show what a place actually feels like.

At LOST iN we explore travel culture in all its forms through hidden restaurants, shops, and local spots far from the typical tourist path. Follow along to stay connected wherever you roam. For travelers craving deeper, more authentic experiences check out travel guides, destination videos, and our membership that unlocks exclusive travel deals, cultural insights, curated city guides, and members-only events.

Connect with us

Website: https://lostin.com/

Instagram: https://www.instagram.com/lost_in_travel/

Facebook: https://www.facebook.com/lostintravelguide

Tiktok: https://www.tiktok.com/@lostin_travel

From medieval old towns and Baroque architecture to lakeside castles, comfort-driven cuisine, and a booming innovation ecosystem, Lithuania blends deep history with modern momentum in a way most American travelers haven’t discovered yet.

Ambassador Varvuolis shares how Lithuania is:

• Showcasing its 700-year-old capital Vilnius, a UNESCO-listed city rich in Gothic, Renaissance, and Baroque architecture
• Offering nature-forward travel with 2,000+ lakes, outdoor adventures, and slow-travel appeal
• Serving up hearty, soulful cuisine—from potato-based cepelinai to refreshing pink beet soup
• Positioning itself as a rising hub for fintech, startups, and digital nomads
• Leveraging CES to attract global entrepreneurs, investors, and innovators
• Investing in AI infrastructure, renewable energy, and human capital for the future

Whether you’re a curious traveler looking beyond Western Europe, a foodie chasing regional flavors, or a founder scouting your next international base, this episode offers a compelling introduction to Lithuania—where old-world charm meets next-generation ambition.

🇱🇹 Learn More & Plan a Visit Explore Lithuania through the Lithuanian Embassy or connect with local consulates in New York, Chicago, and Los Angeles—and if you’re craving Lithuanian food stateside, Chicago is your first stop.

Far beyond the crowds of Cancún, Yucatán offers travelers a deeper connection—to Mayan history, sustainable communities, and a culinary heritage that’s as alive today as it was centuries ago.

Elizabeth shares how Yucatán is:

• Preserving and celebrating living Maya culture, from language to cuisine
• Offering immersive community-based tourism that empowers locals and protects tradition
• Home to award-winning gastronomy, cenotes, and archaeological wonders like Chichén Itzá and Uxmal
• Reviving coastal gems like El Cuyo—Tulum’s soulful predecessor—for travelers seeking quieter, more authentic escapes
• Building a sustainable model of tourism rooted in respect, authenticity, and shared benefit

Whether you’re drawn by ancient ruins, turquoise sinkholes, or handmade tortillas cooked over open fires, this episode shows how Yucatán invites travelers to move slower, look deeper, and experience Mexico beyond the resort brochure.

🇲🇽 Plan Your Journey Discover more at yucatan.travel

Want to dig deeper into a city or neighborhood?

Check out our expertly curated city guidebooks at lostin.com

We pour all of our love for travel into every guidebook, which includes recommendations for hidden restaurants, shops, and activities far from the well-known tourist areas and off the radar of mainstream travel accounts.

We also share daily travel inspiration, city stories, and behind-the-scenes moments across our social channels, follow us to stay connected wherever you roam.

--Connect with us--

Web: https://lostin.com/

Instagram: https://www.instagram.com/lost_in_travel

Facebook: https://www.facebook.com/lostintravelguide

Twitch: https://www.twitch.tv/lost_in_travel

Mike shares how Batch is:

• Building what he calls “the celebration economy”—turning life’s milestones into travel-worthy moments
• Expanding beyond bachelor and bachelorette parties to serve every kind of group celebration
• Using predictive demand to see where travelers are going months before they book
• Empowering small businesses, from boat captains to hibachi chefs, to thrive by plugging into Batch’s ecosystem
• Curating authentic local stays, dining, and activities powered by user data, not algorithms
• Balancing explosive growth with profitability—and why they’ve turned down outside capital for two years
• Betting on community and curation over automation as AI reshapes travel

Whether you’re a party planner, an entrepreneur in the experience economy, or just someone who loves celebrating life with your crew, this episode offers a front-row look at how Batch is redefining group travel—one unforgettable trip at a time.

🎉 Plan Your Next Celebration Download the Batch app and start planning your next group getaway at batch.com.

Want to dig deeper into a city or neighborhood?

Check out our expertly curated city guidebooks at lostin.com

We pour all of our love for travel into every guidebook, which includes recommendations for hidden restaurants, shops, and activities far from the well-known tourist areas and off the radar of mainstream travel accounts.

We also share daily travel inspiration, city stories, and behind-the-scenes moments across our social channels, follow us to stay connected wherever you roam.

--Connect with us--

Web: https://lostin.com/

Instagram: https://www.instagram.com/lost_in_travel

Facebook: https://www.facebook.com/lostintravelguide

Twitch: https://www.twitch.tv/lost_in_travel

From rebranding MLS club Sporting Kansas City to spearheading Airshare’s partnership with the PGA of America and Ryder Cup, Andy’s career sits at the intersection of creativity, strategy, and the business of movement. He brings a marketer’s eye and a traveler’s heart to an industry built on saving the one thing money can’t buy—time.

Andy shares how Airshare is:

• Expanding from regional roots to national scale while keeping a personal, customer-first ethos
• Turning golf partnerships with the PGA Championship and Ryder Cup into long-term brand storytelling
• Offering fractional ownership, jet cards, and aircraft management for flyers who value flexibility over flash
• Making private aviation accessible to the next generation of business leaders and luxury travelers
• Using sports, culture, and hospitality as cornerstones for brand growth and emotional connection

Whether you’re a business traveler chasing efficiency, a golf enthusiast flying to your next tee time, or just curious what it really takes to elevate a brand 40,000 feet above the competition, this episode reveals how Airshare is transforming private aviation into something deeply human—and surprisingly attainable.

✈️ Learn More Explore Airshare’s private aviation programs and their 25-year milestone at flyairshare.com

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.

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 wild
• Turning conservation into a financially viable model that funds national parks and anti-poaching efforts
• Training staff and educating guests to be stewards of nature long after they leave camp
• Designing transformational experiences that help travelers look inward, not just outward
• Expanding into wellness-focused safaris that blend yoga, mindfulness, and immersion in African landscapes
• Envisioning 35 eco-lodges across East Africa to scale both conservation and community impact

Whether 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.

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 experience
• Balancing affordability with luxury, proving “black tie” doesn’t have to mean overpriced
• Expanding into summer with bike rentals, giving operators year-round sustainability
• Scaling through a unique licensing model that empowers local entrepreneurs
• Building authentic community relationships with resorts, hotels, and concierges
• Keeping customer service at the core—hiring personalities first, ski techs second

Whether 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.

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-friendly
• Tapping into partnerships that meet travelers where they already live, dine, and play
• Prioritizing “memory-making” over pure redemption value
• Building a program that speaks to value-conscious families, Gen Z adventurers, and road-trip superfans alike
• Creating an ecosystem where points mean more than transactions—they mean stories

Whether 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.

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/

Brian shares how the Pocono Mountains region is:

• Attracting new and returning visitors year-round, from family road-trippers to luxury travelers
• Leveraging data, storytelling, and even its own 24/7 television network to inform, inspire, and convert audiences
• Building strong partnerships with state agencies and local businesses to elevate small-town tourism
• Navigating trends like short booking windows, user-generated content, and travel inspiration via OTT and apps
• Making travel more accessible, from multi-generational family reunions to last-minute escapes

Whether 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.

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.

As sports tourism surges toward a projected $2 trillion global market, the Aces are emerging as a must-see stop on the Las Vegas itinerary—proving that women’s basketball can drive travel, culture, and economic impact at scale.

D’Andra breaks down how the Aces are:

• Turning championship success into a destination-worthy game-day experience
• Partnering with MGM and the LVCVA to integrate Aces games into broader Vegas travel itineraries
• Taking a quality-over-quantity approach to brand partnerships and sponsorships
• Building player-led storytelling that empowers athletes as creators and media brands
• Positioning the Aces as a cornerstone franchise in both the WNBA and Las Vegas’ sports ecosystem
• Using CES as a platform for inspiration, innovation, and future-facing fan engagement

Whether you’re a sports marketer, brand strategist, or traveler planning your next Vegas trip, this episode offers a compelling look at how the Las Vegas Aces are redefining sports entertainment—and why women’s sports are becoming a powerful engine for tourism and culture.

🏀 Learn More Follow the Las Vegas Aces and their upcoming season to see how championship basketball meets destination-driven storytelling in Las Vegas: https://aces.wnba.com/

From America’s first public wireless-charging road to an EV-friendly Lake Michigan Circuit designed to keep charging stops within reach, Justine breaks down how Michigan is making road trips more seamless for the next generation of travelers.

Ever wonder what a city is like beyond the tourist traps? LOST iN is a travel company built on curiosity...dedicated to the food, fashion, people, and stories that show what a place actually feels like. At LOST iN we explore travel culture in all its forms through hidden restaurants, shops, and local spots far from the typical tourist path.

Follow along to stay connected wherever you roam. For travelers craving deeper, more authentic experiences check out travel guides, destination videos, and our membership that unlocks exclusive travel deals, cultural insights, curated city guides, and members-only events.

—Connect with us—

Website: https://lostin.com/