We aren’t starting our “Ultimate Bucket List” plan from zero. Before we committed to the “10 Countries, 10 Years” challenge, we took a few test runs. Tulum and Puerto Rico were our proving grounds. They weren’t perfect, but they taught us exactly how to handle the logistics of a family of 5.

Puerto Rico: Flexibility is Currency

Puerto Rico was our first family trip involving flights—and man, was I spoiled! I found tickets using Google Explore for under $100 per person. They were so cheap that we decided to bring my mom along for extra adult support. As it turned out, we didn’t really need the extra hands (don’t worry, Mom—we still loved having you there for the memories!).

• The Lesson: Local living is an adventure, not a burden. We stayed in a neighborhood and explored off the beaten path.
• The Win: We discovered that the best memories weren’t the “top 10” attractions, but dancing in the rain on our Airbnb deck.
• The Takeaway: Don’t be afraid to explore beyond the resort gates!

Tulum: Mastering the Logistics

Our first trip to Tulum was where I started honing my real travel-planning skills. I realized that for a family of 5, this wasn’t something I could go into “willy-nilly.” I spent hours combing through blogs, tracking flight trends on Google Explore, and carefully scrutinizing Airbnb listings for the perfect fit.

• The Lesson: You cannot do it all. With three kids, a rigid itinerary is a recipe for a meltdown.
• The Win: We learned to schedule one “big” activity in the morning (like the ruins or a cenote) and leave the entire afternoon open. If we were up for more—YAY! If not, we had plenty of time for relaxing by the pool.
• The Takeaway: It’s better to do one thing well than to do five things while stressed.

What I Carry Forward

Both trips taught me the most important lesson of all: The kids won’t remember the hotel lobby or the flight delays.They will remember the time we all rode four-wheelers down a dirt road to the beach, the time we chased pigeons in the street, and playing with local kids at the park on New Years Eve.

My youngest is graduating high school in just a little over a decade, and I realize the clock is ticking on our “together” years. I’m not just trying to survive the decade; I’m trying to make it count. We are ready for the next 10 years because we know that even when things go wrong, we have each other.

What was the first trip you ever took with your family? Was it a disaster, a dream, or a little bit of both? Let me know in the comments!