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. ✨
What Our Alaska Cruise Taught Me About Slowing Down
I will always remember my first trip to Alaska, and I hope it’s the first of many.
What stays with me most isn’t a single excursion or a checklist moment. It’s the memory of sitting on a lower deck, wrapped in stillness, watching mountains and water slide past as if time itself had decided to be gentle for once. Sometimes we watched for whales. Sometimes we waited a long time and saw nothing at all. And somehow, that waiting was part of the beauty.
There was no rush to fill the space.
That rhythm carried through the entire trip. We were laid back in a way that felt natural, not forced. There was a lot of connection. With each other. With family who came along. With new friends we met somewhere between sea days and shared meals. Conversations unfolded slowly, the way they do when no one is checking the clock.
Even the ports felt different. Unhurried. We wandered more than we planned. We didn’t feel the need to “do it all.” Some of my favorite moments came from stopping into small shops and talking with the people who worked there, asking what it’s like to live and work in these places we were only passing through. Their stories added texture to the trip, grounding it in real life instead of postcard perfection.
Looking back, I realize Alaska didn’t just slow me down while I was there. It changed how I travel now.
I notice myself choosing fewer plans. Leaving room to sit, to watch, to wait. I care less about squeezing in everything and more about how a place feels while I’m in it, and how I feel when I leave. That trip taught me that not every beautiful moment announces itself loudly. Some of them drift by quietly, asking only that you stay long enough to notice.
The best souvenirs are the habits we bring home.
Reds Road Trip: From New York to DC
Baseball has always been more than a game for us.
It’s a reason to travel, a way to mark time, and a thread that keeps pulling us back together, no matter where the Reds happen to be playing.
This summer, that thread took us on a simple road trip: New York City to Washington, DC. Two cities we already knew. Two ballparks. A few days carved out just to follow our team and enjoy being together along the way.
No big agenda. No pressure to see everything.
Just baseball and the road between.
Cheering on the Reds at Citi Field — the first stop on a simple road trip from New York to DC. Baseball, familiar cities, and time together.
🗽 New York City | Citi Field
Our first stop was New York, where the Reds were playing the Mets at Citi Field.
Walking into the stadium, the energy hit immediately. Mets fans everywhere, the buzz of game night in the air, and us in our Reds gear, proudly outnumbered but completely unbothered.
Citi Field feels big and modern, but what stood out most was the sense of history woven throughout the park. The Jackie Robinson Rotunda sets the tone before you even see the field.
View from the stands at Citi Field during Reds vs. Mets — a packed stadium, summer sky, and the energy of game night in New York City.
After the game, we wandered, grabbed food, and let the city carry us for a bit.
Washington, DC | Nationals Park
From New York, we headed south to Washington, DC.
Nationals Park sits along the Anacostia River and carries a calmer, more reflective energy.
Walking toward Nationals Park on game day — fans filling the streets and the energy building before first pitch.
Inside the park, we took our time noticing the murals, history, and the Presidents Race.
Outside the stadium, we slowed down even more, walking monuments and enjoying familiar streets.
🚗 Why This Road Trip Stuck With Us
It wasn’t about chasing highlights or packing the days full. It was about choosing one shared interest and letting it shape the trip.
Two cities. Two ballparks. A few nights away.
That was enough.
Reflection:
If you planned a one- or two-night getaway around something you love, where would it take you?