What We Learned from Seven Weeks Traveling in Italy

With Practical Tips for Your Own Adventures

Thomas here.

Seven weeks in Italy with our family last summer was more than just a vacation—it was an enriching experience that deepened our connections, expanded our perspective, and taught us invaluable lessons about travel and family.

Travel has a way of elevating the simple moments—watching the sunset with loved ones, sharing a meal, or exploring unfamiliar streets—and turning them into cherished memories. As we begin planning this year’s adventures, I’ve been reflecting on what made last summer so special and how those insights can be applied to any trip.

Whether you’re planning a weekend getaway or a month-long escape, these takeaways will help you create richer, more seamless travel experiences.

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1. Plan More Downtime Than You Think You Need

We all know how tempting it is to pack a trip with endless activities. After all, when you’re investing so much in a vacation, it feels counterintuitive to schedule "empty" time. But too much can quickly lead to burnout, and that can undo the magic of the journey.

What We Learned

Six weeks into our trip, near the southern tip of Italy, we hit a wall. The temperatures were sweltering, one of our kids had a bee sting that turned into an infection, and we were running on fumes. For the first time, I felt ready to go home—a feeling I hadn’t anticipated on such an incredible trip.

Looking back, the problem wasn’t the destination or the activities we had planned; it was the pace. Days packed with sightseeing and experiences left no time to recharge or handle life’s inevitable interruptions. We found ourselves falling behind on work, feeling anxious, and, worst of all, unable to enjoy the moment.

Downtime isn’t just a luxury—it’s a necessity. It’s the space where you recover your energy, reconnect with the people you’re traveling with, and adjust to the unexpected. Without it, even the best-planned itinerary can feel overwhelming.

Practical Tips

• Split your days into AM and PM blocks. Alternate between high-energy activities and downtime. For example, explore a historic site in the morning and spend the afternoon by the pool or catching up on work. This approach allows you to recharge without feeling like you’ve “lost” a day.

• Use the 24-hour downtime rule. If you need more rest, combine a PM downtime with the following AM to create a full day’s worth of recovery time. It’s perfect for catching up without sacrificing a calendar day entirely.

• Build in extra planning time. No matter how much you prepare beforehand, you’ll need to adjust your itinerary as you go. A few hours of downtime for reworking plans can save you from chaos later.

• Space out your guests. If you’re hosting family or friends during a longer trip, don’t schedule them back-to-back. Allow time to recharge between visits, so you’re fully present for each group.

• Expect the unexpected. Life doesn’t stop just because you’re traveling. By planning for downtime, you’ll be better equipped to handle the surprises—whether it’s a minor medical issue, a missed reservation, or simply a day when everyone needs a break.