Frequently Asked Questions

A behind-the-scenes look at how we’re making this family adventure work.

But won’t Daxton be too young to remember anything?

We get this question a lot—and it’s a really fair one. At 3 years old, Daxton probably won’t remember the details of every place we go, and even Evelyn, at 7, might retain only pieces of the year. But for us, this trip isn’t only about what they remember—it’s about what we build together while we’re living it.

This year is about being present as a family. It’s about deepening our bond, creating space for Evelyn and Daxton to grow closer as siblings, and giving all four of us time away from the pressures of work, school, and routines to just be together. These shared experiences—trying new foods, navigating unfamiliar places, laughing through misadventures—will shape who we are as a family, even if the kids don’t recall every stop.

And to be honest, it’s about us too. Elisa and I love travel. It’s something that fills us with energy, wonder, and joy. It’s okay to do something adventurous for our own growth, as long as we bring our kids along in ways that keep them safe, connected, and engaged. Their joy deepens ours.

It’s a big question, and one we take seriously. First, we want to acknowledge our immense privilege in being able to do this at all. It’s not cheap. But there are several things that have made it possible for us.

One major factor is that Elisa is continuing to work virtually for Treasure Trunk Theater. Her incredible team is holding things down in Brooklyn, and that stability gives us financial continuity even while we’re on the road. We’re also renting out our apartment for the year, which helps offset living costs while we’re away.

And then there’s the magic of credit card points. We spent over a decade unintentionally racking up rewards, and now we’re cashing them in—big time. Many of our hotel stays, especially through Hyatt, are booked entirely on points. We’ve become strategic about budgeting and cutting back in areas like long-term savings and childcare to prioritize this experience. Is it expensive? Yes. But it’s also the kind of experience we may never be able to do again, and we’re making intentional choices to prioritize it now.

We’re doing a little of both—and very intentionally so. After talking with other traveling families, we heard over and over that if you treat this like a year-long vacation, you’ll burn out fast. It’s too much movement, too little rest.

So we’re building a rhythm into our year that we call “running arounds and sit-downs.” The running arounds are our active travel stretches—moving quickly from place to place, seeing the sights, staying in hotels, and soaking up new places. The sit-downs are our breathers—2 to 4 weeks in one location, usually in an Airbnb, where we can cook meals, do laundry, let the kids have structure, and catch our breath.

This allows us to go deep in some places, while still exploring broadly. It also gives the kids a sense of rhythm and predictability, which we think is going to be key to keeping everyone grounded on the road.

We started by dreaming big—what are the places we’ve always wanted to see but never had the time or the distance to justify? Asia topped the list. We’d been to Vietnam once for a close friend’s wedding and absolutely fell in love, and ever since, we’ve wanted to go back. But from New York, it’s just… really far.

We also looked at safety, ease of travel with kids, and the seasonal climate in each location. We’re trying to avoid extreme heat or rainy seasons by hitting places in either prime or shoulder seasons. That kind of logistical thinking shaped a lot of our route.

Lastly, cost of living played a role. Places like Southeast Asia are far more affordable than Europe or North America, so that helped us stretch our budget further. We tried to choose locations that offer cultural richness, nature, food, and a sense of adventure—while also giving us a diverse look at the world.

Planning this trip has been its own full-time job. While some families take a “show up and figure it out” approach, that’s not us—especially not with young kids in tow.

We’ve leaned heavily on ChatGPT (seriously—it’s been great for brainstorming and checking logistics), plus lots of Googling and reading blogs. We found Reddit and travel forums incredibly helpful for figuring out how to use points strategically, and we’ve gotten invaluable advice from friends who’ve done similar trips.

We also want to give a shoutout to Rachel Lipson, who helped guide our thinking around travel hacking and using Hyatt points effectively. On the ground, Google Maps reviews tend to be more reliable than TripAdvisor these days, though we’ve learned to read reviews through the lens of our own preferences. (We like bougie coffee. A $7 latte might be a one-star experience for someone else—but for us, it’s heaven.)

The key has been doing deep research, asking lots of questions, and recognizing that no one source is perfect. You have to triangulate your own truth.

We’re packing surprisingly light for a year abroad.

Here’s what we’re bringing:

  • 3 Briggs & Riley international carry-on suitcases (durable, compact, and built to last)

  • 2 travel backpacks that meet carry-on requirements (one from Aer and one from Elisa’s brand)

  • Evelyn’s smaller backpack, which will double as our day bag when we explore cities

  • A YoYo travel stroller, upgraded for this trip after our last one survived 8+ years

That’s it. We’re aiming for flexibility and ease of movement—and we’ll re-evaluate along the way if we need to shed or swap gear.

Yes—we had quite the checklist. We worked closely with a travel health clinic in NYC, along with our pediatrician, to identify the vaccines recommended for the countries we’re visiting. That included things like hepatitis, typhoid, and other region-specific immunizations.

We also filled prescriptions for medications like malaria pills, even if we might not need them everywhere. The goal is to be prepared, not paranoid. We explored getting some vaccinations while abroad, but with young kids, we decided it was best to take care of everything before departure, under the guidance of our trusted doctors.

U.S. insurance doesn’t cover extended global travel, so we had to get separate travel medical insurance for our family. After a lot of research, we settled on a reputable provider (link coming soon) that offers global emergency coverage, reimbursement for health expenses, and even emergency evacuation if needed.

It costs us about $3,500 for the year, but it covers all four of us for millions of dollars in potential coverage. Each country has its own healthcare system, and costs can vary wildly—from a $12 emergency room visit in London to something far more expensive in a less-resourced setting. This gives us peace of mind.

Since Daxton is only 3, we’re less focused on formal education for him. That said, we plan to keep him engaged with reading, play, exploration, and whatever Evelyn’s learning—he’ll absorb a lot just by being alongside her.

For Evelyn, we’ve officially registered her as a homeschooled student through NYC’s Department of Education. We met with her principal and teachers, who were incredibly supportive and gave us guidance on what to prioritize—especially math and writing. We’ll be using a combination of online tools, worksheets, and self-guided learning.

One thing we’re really excited about is having Evelyn read about the countries we’re visiting before we arrive. She’ll have her own Kindle, and we’ll use books and history as a bridge to real-world experience. We’re aiming for a rhythm where we have structured “school time” a few days each week—often while Elisa is working remotely.

Yes, absolutely.

We love to travel, but we love New York City even more. Brooklyn is our home. It’s where Elisa’s business is based, where our kids go to school, and where we’ve built a community we care deeply about. Mike’s professional network and legal credentials are all rooted here, too.

This is a pause—not a relocation. We’ll be back in summer 2026, ready to reintegrate into the life we’re so grateful to return to.

Mike doesn’t know—and that’s the point.

After 15 years leading a nonprofit focused on youth and racial justice, stepping away was a huge decision. But this year is a chance to ask the big questions: What kind of work feels meaningful now? What skills still matter? What kind of life do we want to build next?

There’s a list of possible futures—nonprofit leadership, public service, law, philanthropy—but for now, Mike’s focusing on the present. On being with the kids. On reflecting. And on letting the next path reveal itself through lived experience.

Treasure Trunk is in great hands. Elisa has built an incredible team, and she’s continuing to work remotely to help lead and support the business from abroad. The goal for this year is consistency—making sure the programming remains joyful, inclusive, and magical for the kids of Brooklyn.

There are some exciting ideas for the future, including possible expansion, but for now, Elisa’s focus is on staying grounded in the mission while being present with our family.

Daxton’s reaction was exactly what you’d expect from a 3-year-old who loves transportation:

“Airplanes?”

When we said yes—many—he was thrilled. He asks about them regularly.

Evelyn’s response was more layered. She has deep friendships, loves school, and is emotionally rooted in our Brooklyn community. When we first told her, she cried. She was afraid she’d fall behind, that she wouldn’t be with her classmates. But after a lot of love and a gentle explanation (shoutout to Elisa, master of talking with kids), she got it. She wiped her tears and said, “Oh! I’m very excited!”

Since then, she’s been all in—especially when it comes to Japan. She’s already planning to write a book about her time there.

Surprisingly… Mike.

He’s usually the lawyer-brain, spreadsheet-loving planner, while Elisa is the spontaneous, artistic free spirit. But during a run in late 2024, Mike had two realizations: it was time to step away from the nonprofit he’d led for 15 years, and if we were ever going to travel the world as a family, now was the moment.

He came home, pitched the idea (sweaty and wild-eyed), and Elisa—ever the grounded one—told him to go take a shower. But over time, it clicked. During a family trip to Sicily soon after, we both felt it: There’s no better time. And if not now… when?

No more than we are in New York.

We’re staying informed, planning smart, and being thoughtful about where we go. There are some regions we’ve always dreamed of visiting that we’re skipping—for now—due to instability or conflict. We’ve also built flexibility into our itinerary so we can adjust if needed.

Traveling with kids means you’re always alert. But it doesn’t mean you stop living. We’re not taking reckless risks—but we’re also not going to let fear dictate our story. We’ll stay together, stay aware, and stay open.