We Planned a Reds Road Trip. Milwaukee and Chicago Had Other Plans.

So remember when I told you Jamie, Lance, and I were road-tripping to see the Reds?

Yeah. About that.

We ended up in Milwaukee and Chicago, which is either a wrong turn or the best decision we've made all year, depending on how you look at it (I'm going with the second one).

Here's what actually happened.

The Hotel Room That Ruined Me For All Other Hotel Rooms

We stayed at the Hilton Garden Inn Milwaukee Downtown, which was lovely and fine and everything a hotel should be. But it's the second stop, Chicago's Hotel Zachary, that I need you to sit down for.

Our room looked directly out at the Wrigley Field Marquee. Not "if you lean out the window and squint." Directly. Out. At. It. Jamie caught me just standing at the window for a solid five minutes like I'd never seen a light-up sign before. I had not seen one like this before.

The view from our room at Hotel Zachary: Wrigley Field’s marquee, a sea of Cubs fans, and the exact moment I understood why people book this room on purpose.

SafeHouse: Milwaukee's Worst-Kept Secret Speakeasy

If you know, you know. If you don't: there's a password. There's a whole bit. Lance took it far too seriously and I will not be elaborating further because half the fun is not knowing what you're walking into.

What I will say is that it's exactly the kind of slightly-absurd, very-fun stop that makes a trip feel like an adventure instead of an itinerary. Ten out of ten. Bring a sense of humor.

The Bar Shuttle Wristband Incident

The Milwaukee Brat House has a shuttle that runs on a wristband system, and somewhere between brat number two and wristband logistics, this became one of my favorite unplanned parts of the entire trip. I'm not going to explain it well in one paragraph. It deserves its own post. It's getting one.

Murals, Bloody Marys, and a Bronze Fonz

Black Cat Alley is a full outdoor mural walk that I did not expect to love as much as I did — genuinely one of those "okay, Milwaukee, you're cooler than I gave you credit for" moments.

We spent way too long following painted koi fish down an alley like they’d lead us somewhere. They did not. Worth it anyway.

The Milwaukee Public Market gave us a Bloody Mary that came with what I can only describe as a full garnish buffet balanced on top of the glass. There's also a bronze statue of the Fonz on the Riverwalk, which — yes, we took the picture, no, I'm not sorry.

The Game Itself (Both Of Them)

Brewers at American Family Field, then Cubs at Wrigley a few days later — a 23-3 win for the Cubs over the Padres, in front of a crowd that stayed loud for all 27 outs. Two completely different stadium personalities, two completely different energy levels, and somehow both exactly what I needed.

So...

What I can do right now: if you want to see Milwaukee and or Chicago, I can book the exact hotels we stayed in — same Hilton Garden Inn, same Hotel Zachary marquee view if it's available — no group required.

Email me at tracy@harmonyhorizon360.com and I'll get you set up.

If enough of you want to do this together down the road, exactly as we did it? That's where the group trip lives. For now: go see it and tell me how it goes.

Related Posts:

See where it started: Taking Our ND Son to Milwaukee — Here’s How We’re Planning It Differently — Harmony Horizon 360 Travel

See other Baseball City Trips: Cincinnati Reds Game Day Trip: Brunch, Breweries, and a Loss We're Still Processing — Harmony Horizon 360 Travel

What a Sea Day on a Caribbean Cruise Actually Looks Like (When You Stop Trying to Fill It) 💛

I used to think sea days were the days you just got through.

Like, okay, no port today, guess I'll find something to do. Wander the ship. Eat too much. Wonder why I'm not relaxing when I paid actual money to be here relaxing.

It took me embarrassingly long to figure out that I was doing sea days completely wrong.

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Here's what nobody tells you before your first cruise: sea days are not the filler between the good stuff.

Sea days are the good stuff.

Or at least, they can be. Once you stop trying to schedule them like a port day with no port.

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The moment I finally got it

We were somewhere in the Caribbean — I want to say it was day three — and I had a loose plan. Maybe the pool. Maybe a class. Maybe that thing on deck I kept walking past.

I did none of those things.

I found a chair on a quiet part of the deck, got a drink, and just... stayed there. For a long time. Long enough that Jamie came looking for me. Long enough that I watched the water change colors as the light shifted. Long enough to have an actual thought that wasn't connected to a to-do list.

That was the day I understood what sea days were actually for.

They're not for doing. They're for coming back to yourself.

What a sea day actually looks like for us now

We don't plan sea days the same way we plan port days. That's the whole secret, and it sounds obvious when I say it out loud, but it genuinely took a couple of cruises to land there.

Here's what a good sea day looks like in real life — not the brochure version:

A slow morning. No alarm. Room service coffee or a walk to the buffet depending on how ambitious we feel. We don't make this decision in advance. That's the point.

Some version of movement, but only if we want it. Sometimes that's the gym. Sometimes it's walking a few laps around the deck and calling it done. Sometimes it's neither and that's fine too.

A chunk of time with nothing scheduled. This is the part people fight. We are conditioned to fill empty time. Resist it. The empty time is where the good stuff happens — the real conversations, the napping that actually restores you, the moment you look up from your book and realize you feel genuinely calm.

One thing that sounds fun, not one thing that sounds productive. Trivia. A cooking demo. The pool. A movie. Something that has no purpose other than enjoyment. This is harder than it sounds for people who run on output.

Dinner with no rush. Sea day dinners are some of my favorites. Nobody is tired from walking ten thousand steps through a port. Nobody is sunburned and dehydrated and pretending they're fine. Everyone just shows up and enjoys the meal.

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What I stopped doing on sea days

Filling every hour because I felt guilty about "wasting" the day.

Making a list of ship amenities to hit like I was checking off a port itinerary.

Worrying about whether I was relaxing correctly. (Yes, I did this. No, it did not help.)

Comparing my sea day to anyone else's sea day. Some people want to be at the pool with a frozen drink by 9am. Some people want to read for six hours. Both are correct.

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The thing about sea days and real life

At some point during our last sea day I caught myself looking around for something to do. That low hum of shouldn't I be somewhere? Checking something?

And then it hit me — I hadn't felt that in hours.

My body had gotten so quiet it didn't know what to do with itself. And for one very confused second, that felt alarming.

And then I laughed. Because that feeling — that weird, unfamiliar stillness — that's what rest actually feels like when you've been running on empty long enough to forget the difference.

That's the whole Reset & Roam thing in one day, honestly. Travel isn't always about going somewhere. Sometimes it's about finally stopping long enough to arrive where you already are.

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If you've been on a cruise and found yourself restless on sea days, try something on your next one. Make one plan. Just one. And let the rest of the day happen.

You might be surprised what shows up when you stop trying to fill the space.

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Thinking about experiencing this for yourself on a group cruise? I'm in the early planning stages of a hosted group sailing and would love to have you along. →  Join the interest list