Travel, Travel Planning Tracy Woods Travel, Travel Planning Tracy Woods

How We’re Choosing Our Next Reds Road Trip (And What We’re Doing Differently This Time)

There’s something about planning a trip that starts long before anything is booked.

It usually begins with a feeling.

For us right now…
it’s simple:

We need something to look forward to.

Not a big, complicated vacation.
Not something that takes weeks to recover from.

Just a trip that feels easy…
fun…
and a little like us again.

We’ve done a few Reds trips now — different cities, different stadiums, and different versions of how we travel. Some of our favorites have been the ones where we slowed down enough to actually take it in, like when we spent time exploring the city beyond just the game.

We haven’t planned everything yet.

We haven’t mapped every stop or booked every detail.

But we have decided something more important:

how we want the trip to feel.

Walkable.

Simple.

Walkable. Simple. Room to wander.


That’s become one of the biggest priorities for us, especially after realizing how much more we enjoy trips where everything is close and easy to explore on foot.

Time to sit somewhere with a drink and just take it all in.

A game in the middle of it all…
not the only thing.

That’s the shift for us.

We used to plan around the game.

Now we’re planning around the experience…
and letting the game be part of it.

We’re starting with the basics.

Looking at schedules.
Picking a city that makes sense.
Finding a place we can stay where we don’t have to drive everywhere.

Because we’ve learned…
how a trip flows matters more than how much you fit into it.

There’s something else we’re doing differently too.

We’re not trying to get it perfect before we go.

We’re letting some of it stay open.

Because some of our favorite moments on past trips…
weren’t planned at all.

They were the in-between moments.

The walk to nowhere in particular.
The random conversation.
The place we almost didn’t stop.

So this trip?

It’s still coming together.

We’ll choose the game.
We’ll lock in the stay.
We’ll sketch out a loose plan.

But we’re leaving space.

For fun.
For connection.
For whatever the trip turns into once we’re actually there.

And honestly… that’s part of what I love most about this.

The planning isn’t just logistics.

It’s a reminder that we get to choose how we spend our time.

That we can build something to look forward to…
even in the middle of regular life.

If you’re thinking about taking a trip this year…
especially something simple like a weekend away…

you don’t have to have it all figured out.

Start with how you want it to feel.

Then build from there.

💛

What We’re Prioritizing This Time

  • Walkable location

  • One anchor event (the game)

  • Open time built in

  • Simple plans over packed schedules

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Travel Planning, Gentle Travel Tracy Woods Travel Planning, Gentle Travel Tracy Woods

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. ✨ 

💛 If you enjoy thoughtful travel and connection-first trips, join the newsletter here.

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