For entrepreneurs, “vacation” is a loaded word.
It usually means one of two things: either you unplug and your business momentum stalls, or you stay plugged in and never actually rest.
I just got back from a three-week trip to Italy with my family, and I’m here to tell you there’s a third way. This wasn’t a vacation. This was a life integration experiment.
We didn’t just see the sights; we lived, worked, and explored in a way that proves you don’t have to hit the brakes on your life to build your business.
Here’s the truth: the goal isn’t work-life balance. It’s work-life integration.
Here’s how my trip went.
Table of Contents
Boundless Life
We didn’t just book an Airbnb or a hotel and hope for the best. We were strategic. We found a program called Boundless.life designed specifically for families like mine.
Boundless.life builds special communities for families in beautiful places around the world. They provide ready-to-live-in homes, shared work spaces, and hands-on learning programs for kids. Their goal is to help families with similar interests connect with each other so they can live, work, and travel together while experiencing the local culture of each place they visit.
We stayed in Pistoia, a little town in Tuscany that became our home base.
Here’s how this program they eliminate the friction:
- A co-working space for me to stay productive.
- A pop-up school for my son to learn and connect.
- A pre-arranged home, taking all the logistical headaches off the table.
Bottom line: this structure gave us the freedom to immerse ourselves in the culture and connect with a community of other families doing the exact same thing. No stress, all upside.
Gallery
Here are more photos I took on this trip.
Core Memories
So, what does that kind of freedom get you? Moments that hit different.
It’s not about checking boxes off a tourist list; it’s about core memories.
These are my top three most memorable moments from the trip:
- Venice Gondola. Yeah, it’s a cliché, but seeing the city from the water with my dad, who was visiting from Lithuania for the first time, was next-level. Some things are famous for a reason. That’s a core memory.
- Pistoia at Night. This is where you find the authentic energy. We had long, two-hour family dinners every night, surrounded by locals, not tourists. The food was insane, but the real takeaway was feeling the pulse of a real Italian town after dark.
- The Swiss Alps. We took a side trip to Switzerland. Standing there and seeing the sheer scale and beauty of the Alps for the first time… it just resets your perspective on what’s possible.
Try Italy
My biggest piece of advice for anyone thinking of doing something similar? Go small.
Forget the chaotic tourist centers of Rome or Milan.
The magic is in the smaller towns where you can actually connect with the community and feel the rhythm of daily life.
That’s where you’ll find the best food, the most genuine people, and the experiences that actually stick with you.
Ditch the checklist and find the connection.
Conclusion
This trip was never about escaping work. It was about proving that an epic life and a thriving business can—and should—coexist.
The supportive, growth-oriented community we found in Italy is the exact kind of environment I work to build for every entrepreneur I coach.