How I Plan Trips Without Overplanning Them ✈️

Travel planning used to feel like a performance. I thought being “prepared” meant having every hour accounted for, every option researched, every moment optimized. And honestly, it stole a lot of joy. I was so focused on doing it right that I forgot to let myself actually look forward to the trip. 

These days, planning looks different. Softer. More human. 

This week was a perfect example. Jamie and I spent a few evenings tossing around ideas — maybe a quick night away somewhere close, maybe a cozy couples hot‑tub room, maybe a weekend trip a little farther out. Nothing urgent. Nothing forced. Just exploring possibilities the way you’d wander through a store without needing to buy anything 🛍️. 

And the next day we’ll sit down and book our excursions and flights for our April cruise. Even that feels lighter than it used to. Instead of treating it like a task to check off, it feels like a small moment of anticipation ✨. A reminder that something good is coming. 

Where Overplanning Used to Steal Joy 😣 

For years, I believed the only way to avoid stress was to plan everything. But the truth was the opposite. The more I tried to control every detail, the more pressure I put on myself — and the less present I was once the trip actually started. 

I’d get so wrapped up in the schedule that I’d miss the moment right in front of me. 

The Boundary I Build Into Every Trip Now 🚧 

Now, I give myself one simple boundary: 

If a plan starts feeling like a rule, I loosen it. 

That’s it. 

 If something feels heavy, I step back. 

 If something feels rushed, I slow down. 

 If something feels like an obligation, I let it go. 

It’s the gentlest boundary I’ve ever set, and somehow the most effective. 

Leaving Space for Things to Unfold 🌙 

One of my favorite parts of travel now is the space I leave open on purpose. Not empty time — open time. 

Like the night Jamie and I wandered into a tiny café on a whim because the lights looked warm and the music sounded good. That moment wasn’t on any itinerary. It wasn’t researched or bookmarked or saved on a list. It just happened because we weren’t rushing to the next thing. 

That’s the kind of magic I want more of. 

Planning Without Turning It Into a Job 🧘‍♀️ 

Planning can support joy without suffocating it. It can give you a sense of direction without boxing you in. It can help you feel prepared without demanding perfection. 

And sometimes the lightest planning moments are the sweetest — like scrolling through hotel rooms and laughing together at the ones with hilariously dramatic décor. (Why do so many places have neon lights behind the bed now? Who decided that was the vibe 😂) 

Travel doesn’t have to be serious to be meaningful. 

It just has to feel like you. 

You’re allowed to leave room for magic. ✨