Roamaroo

In this episode of the Roamaroo Podcast, we sit down with Jenn and Mornee Sherry to talk about what it’s really like to raise a family on a sailboat in the Caribbean. We get into the realities behind the dream, from tight quarters and constant movement to the unexpected freedom that comes with life at sea. They share how this lifestyle has shaped their kids, what day-to-day life actually looks like, and the tradeoffs most people don’t consider when imagining a life like this. We also talk about what pushed them to make the leap, what they’ve learned along the way, and how redefining “home” has changed their family in ways they never expected. 

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In this episode of the Roamaroo Podcast, we sit down with two of the most creative people we know, Elizabeth Higgins-Clark and Lauren Pomerantz. Lauren is an Emmy Award–winning writer who has worked on The Ellen DeGeneres Show and Saturday Night Live, and Elizabeth is a writer, actress, and the granddaughter of the legendary Mary Higgins Clark. Together, they created Wooby and Fotty, now the #1 kids show on YouTube, a musical puppet series about two security blankets helping little kids navigate big feelings. We talk about what it takes to build a creative show from scratch, what it’s like to work together as a married couple, and how they manage to travel with twins along for the ride.

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In this episode of the Roamaroo Podcast, we unpack what it really felt like to come back to the United States after months in Italy, and why the hardest part wasn’t leaving, but returning. This conversation digs deep into the differences between parenting in Italy versus parenting in the United States. We discuss how place shapes identity, what it means to raise kids in a system versus in a culture, and how Italy impacted our parenting style. We share how our experience with Boundless Life challenged our assumptions about education and daily life and we ask a bigger question: is Italy a better fit for our family?

400 Euro Off Boundless Life: https://refer.boundless.life/COLSTO79

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In this episode of The Roamaroo Podcast, Scott and Collette explore what worldschooling really looks like on the ground in Italy with Boundless Life, beyond the highlight reel and into daily life.

We talk about why we chose Italy, how the Boundless Life program blends structure with curiosity, and what it feels like to watch children learn through culture, community, and real-world experience rather than worksheets alone.

This conversation dives into the emotional side of alternative education too: the questions parents wrestle with, the courage it takes to step off the traditional path, and how slowing down can regulate both kids and adults. It’s not about rejecting school as we know it, but expanding the definition of education, and trusting that when children feel safe, connected, and inspired, learning happens everywhere.

400 Euro Off Boundless Life: https://refer.boundless.life/COLSTO79

Book a babysitter in Europe with Tripsitta: https://www.tripsitta.com/partners/roamaroo

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In this episode, we explore packing light with kids and why it has reshaped the way our family travels. We return to a moment in Cinque Terre, Italy, when a rogue wave drenched us and every perfectly packed item we carried, a reminder that preparation can only take you so far. The rest requires adaptability.

We explain why we are firmly #TeamCarryOn, even with children, and why overpacking is often anxiety disguised as organization. More belongings do not make travel smoother. They increase cognitive load, amplify stress, and quietly pull us out of the present moment. We also reflect on how packing less gives children agency, teaching them responsibility and confidence through choice.

Ultimately, this episode reframes packing as a practice in trust. Packing light is not about deprivation. It is about freedom. It is about letting go of control and making room for presence, resilience, and the kind of travel that teaches us who we are.

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In this episode, we tackle the question so many parents think but rarely say out loud: is traveling with kids actually enjoyable, or is it just parenting in a different location? We react to a viral video that struck a nerve and reflect on our earliest trips as parents, the ones marked by fear, second-guessing, and that heavy feeling of doing it all without a safety net.

We unpack the difference between vacation and travel, and explore how the loss of the village in modern parenting has made everything feel harder, including leaving home. When you are carrying the logistics, the gear, and the emotional weight alone, even the idea of travel can feel overwhelming.

But we believe family travel is not about performing or getting it right. Confidence does not come before the trip, it comes because of it. You do not wait until fear disappears. You move forward with it. The goal is not perfection. It is presence, participation, and building resilient families one imperfect trip at a time.

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Do you feel like the price of travel is just too much? In this episode, we break down the real, practical ways families can save money without sacrificing the magic of travel. From swapping your house for a Dutch mansion or a Disney-area villa through HomeExchange, to choosing Airbnbs that save you hundreds in meals and laundry, to RV adventures, national parks, geo-arbitrage, and even the secrets of shoulder-season deals—this episode is packed with strategies that make travel affordable again.

We talk openly about $10k summers, overpriced hotels, and the cultural myths that keep families thinking travel has to be expensive. 

If you’re ready to stop overpaying for travel and start exploring the world in a way that’s financially sane, deeply meaningful, and actually doable for real families—this episode is your new playbook.

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In this episode of the Roamaroo Podcast, we sit down with Seth Picconi, a former compliance officer who spent 15 years ensuring people followed the laws and regulations that govern global finance—before turning that same precision and purpose toward a more human mission. When Seth’s father suffered a stroke and became disabled, travel suddenly looked different through his family’s eyes. That experience inspired him to create TravelMates, a company dedicated to making travel more accessible for people with disabilities. Drawing on his international background and years living in Australia, Seth shares how his global perspective shaped his family’s ethos, why he walked away from corporate life, and how he’s now working to bring accountability, equity, and empathy to the world of accessible travel.

Find Seth on Instagram at @travel_mate_s and https://www.travelmates.io

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Andrea Leblang, Founder of Elite Travel Arrangements, has planned everything from romantic European escapes to million-dollar vacations for the world’s most discerning travelers, but her personal journey is as meaningful as the ones she designs. Andrea shares how travel has made her more mindful, grounded, and connected to the world around her. From curating transformative experiences for ultra-high-net-worth clients to raising her daughter as an American expat in the Netherlands, Andrea reflects on how living abroad in over 60 countries has expanded her worldview and her heart. This episode dives into the art of mindful luxury, building a life rooted in cultural curiosity, and how the most extraordinary journeys ultimately lead us home to ourselves.
Follow Andrea on Instagram @etaescape and visit her website at https://www.elitetravelarrangements.com/

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No, we’re not crazy — but yes, we’re doing it again! Last year, we packed up our lives and moved to France… only to return home sooner than expected. But this time, we’re doing things differently. In this episode, we share why we’re giving Europe another shot — this time in Italy — and how we’re partnering with Boundless Life, a company that helps families like ours live abroad seamlessly, with housing, schooling, and community all set up.

From what we learned in France to why Italy feels like the perfect fit, this episode dives into what it really takes to build a new life overseas — with a little less chaos and a lot more intention. 🇮🇹✈️

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