Should We Plan a Mediterranean Cruise? (Asking For Myself, At 11pm, With Seventeen Tabs Open)
It's 11:14pm. Jamie is asleep. I am not asleep. I am doing the thing where I open one cruise line's website "just to look," and ninety minutes later I have seventeen tabs open, a spreadsheet I didn't mean to make, and a very strong opinion about balcony cabins on the port side.
This is how it always starts. Not with a decision. With a spiral.
Here's the thing — we've actually done the Mediterranean before. A cruise with friends, years ago, before Reset & Roam was even a phrase I said out loud. We ate our body weight in bread. We got lost in a way that was charming for the first hour and character-building for the second. We came home different, in that quiet way good trips do that to you.
So you'd think going back — again by ship — would be the easy part. It is not the easy part.
Because now I'm the person who plans other people's dream trips for a living, which means I am incapable of just looking at a cruise itinerary and going "sure, that looks nice." I am looking at port days and mentally scoring them for pace. I am asking whether seven ports in seven days is a vacation or an endurance event. I am doing this at 11pm on a Tuesday for a trip that is not booked, not planned, and not even fully agreed upon.
Jamie's official position, when I bring it up over dinner, is "sure, let's do it," delivered with the same enthusiasm he'd use to agree we should probably clean the garage eventually. Supportive. Vague. Not actually helpful.
So here's where we actually are, honestly:
• We know we want to go back.
• We do not know if it should be a cruise or a slower land trip, round two.
• We do not know when — 2027 is spoken for with Alaska, so realistically we're talking 2028.
• We are considering if we do cruise it, wanting fewer ports with more hours in each one, not the itinerary that brags about hitting five countries before breakfast.
That last one is the part that actually matters. Because the question underneath "should we plan a Mediterranean cruise" isn't really about the Mediterranean. It's the same question that's underneath every trip I help plan: are we building a trip that fits how we actually like to travel, or are we building a trip that looks good on paper?
Gentle pace and an exciting trip aren't opposites. Tonight I'm saying it to myself, with seventeen tabs open, trying to believe it applies to my own vacation and not just everyone else's.
I don't have an answer yet. I have a spreadsheet, a sleeping husband, and a trip that's still just an idea we keep circling back to. That's honestly where most good trips start — not with a booking, but with somebody staying up too late, still curious.
If you want to follow along as we actually figure this out — cruise or no cruise, 2028 or someday — that's exactly what the Roam newsletter is for. I'll show my work, tabs and all.
Join the Newsletter if you want to stay informed on our travels, both past and upcoming.
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.
—
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.
—
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.
—
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.
—
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.
—
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
What Alaska Did to My Sense of Time (And Why I Keep Thinking About It) 💛
I ordered reindeer sausage from a café in Alaska because the sign on the door told me to.
Not literally. But it was RIGHT THERE, and I am not the kind of person who walks past reindeer sausage and does nothing about it. That is not how I travel. That is not how I live.
It was amazing, for the record. Slightly smoky, a little sweet. I think about it more than I should.
That moment — seeing something unexpected and just going for it — is kind of the whole story of Alaska for me. I went in knowing it would be beautiful. I did not expect it to be the kind of beautiful that makes you go quiet without meaning to. The kind that makes you put your phone down not because you remembered to, but because you forgot it was there.
I kept waiting for a lull. You know that feeling on a trip where you've done the big thing and now you're just killing time until dinner? I kept bracing for it. It never came.
The wildlife showed up like it had somewhere to be and was just passing through — which, it turns out, it was. The history was layered and surprising and kept making me want to ask more questions. The people we met, both locals and the folks we cruised with, were the kind that make you think why don't I know more people like this at home? And the scenery kept delivering in a way that felt almost unfair. Like Alaska knew exactly what it was doing and had absolutely zero humility about it.
In Juneau, we had one of the best excursions of the whole trip — the kind that hits every note without you being able to explain exactly why afterward. (If you want the full breakdown of our favorite stops, I wrote about those here.) And then, the moment the excursion ended, the sky opened up. Not a sprinkle. A full, dramatic, Alaska-is-done-with-you-now downpour. We made it back to the ship. Others from different excursions weren't so lucky — the storm came in fast and not everyone got back before it got serious.
We stood on deck watching the rain and I thought: we timed that perfectly and it had absolutely nothing to do with us.
That's travel. You plan everything you can and then you stand back and let the weather decide the ending. Alaska is very comfortable making that call for you.
I talk a lot about intentional travel — slower pacing, breathing room, trips that actually feel good instead of just looking good. Alaska didn't require me to try for any of that. It just was that. There was nowhere to rush to. No FOMO. The place itself had this quality where the urgency I carry around at home simply didn't make the trip with me. I've written before about why travel isn't our escape — it's how we maintain our marriage and Alaska was the clearest example of that I've ever had.
I came back slightly more patient. Slightly more willing to look at something without immediately thinking about what comes next. I noticed when it started to fade — that slow exhale that Alaska gives you — which is how I knew it had been real.
I'm in the early stages of putting together a small hosted group cruise to Alaska for 2027 — because I want to bring people there who need exactly what I got. Not the reindeer sausage specifically. (Although truly, do not rule it out.) But that feeling of being somewhere so genuinely big that your regular-life problems shrink down to a manageable size. Where you can't rush the glacier. Where the wildlife is on nobody's schedule but its own.
If you've ever thought Alaska someday — I want to hear from you. Because someday is a lot better when you're not going alone.
Want to be first to know when spots open up? Reset and Roam interest list. I'll reach out personally when we're ready.
I Don’t Plan Trips to Get Away… I Plan Them So Life Feels Better When I Come Back
It Didn’t Start the Way I Thought It Would
I used to think travel was about getting away.
From the stress.
From the noise.
From everything waiting for me at home.
But the truth is…
the best trips I’ve ever taken didn’t help me escape my life.
They helped me come back to it differently.
This Trip Was Different
We just got back from a two-week cruise with friends and family.
And if I’m being honest… I needed it more than I realized.
Life at home had been stacking up.
Work felt heavy.
The house felt loud.
My brain felt full.
So instead of planning something packed and busy,
we did the opposite.
We chose a longer cruise.
More time.
More space.
More room to breathe.
And yes… maybe a few too many port days (lesson learned),
but in between those, there was something I hadn’t had in a while.
Time to just be.
Time to sit with Jamie without rushing off to the next thing.
Time to talk, laugh, wander, or do absolutely nothing.
Time to think without immediately needing to solve anything.
And somewhere in all of that…
I reset.
Just enough to feel like myself again.
How I Plan Now
When I plan trips now, I think about them differently.
Not:
“How much can we fit in?”
But:
“How do I want to feel while I’m there… and when I come back?”
That changes everything.
It means:
Leaving space in the schedule
Choosing walkable, easy locations
Not overloading every single day
Building in time to sit, reflect, and connect
Because the goal isn’t to come home exhausted with great pictures.
It’s to come home lighter.
Finding Our Spot
This might sound simple… but it matters.
We always find “our spot.”
On this cruise, it was a quiet area where we could sit with a drink,
watch the ocean, and just exist for a minute.
No pressure to be doing something.
No agenda.
Just a place where we knew we could land.
Those little anchor spots become part of the reset.
Things I’ve Learned Along the Way
A few things I’ve learned the hard way:
Not every port needs to be an excursion
You don’t have to say yes to everything
Rest is part of the plan, not a break from it
The best conversations don’t happen when you’re rushing
Sometimes the best part of the trip is the part you didn’t plan.
We’re actually planning our Reds weekends the same way now — less packed, more intentional.
What I’d Go Back For
Not just places… but feelings.
I’d go back for:
Slow mornings with nowhere to be
Laughing at dinner without checking the time
That feeling when your shoulders finally drop
Real conversations that don’t get cut short
That’s the part I want again.
What Travel Really Does for Me
I don’t plan trips to get away from my life anymore.
I plan them so I can come back to it better.
More patient.
More present.
Less overwhelmed.
Because travel, for me, isn’t an escape hatch.
It’s a reset button.
And honestly…
It’s become one of the best ways I’ve found
to take care of the life I’ve already built. 💛
If you’ve been feeling that pull too…
I’ve started putting together a few trips (some simple, some a little bigger)
and you can join the interest list here:👉 Join the Reset and Roam Trip List
No pressure, just a way to see what we’re planning.
What Sea Days Are Really Like on a Cruise (And Why We’ve Learned to Love Them) 💛
Most people think the best part of a cruise is the ports.
After a few cruises, we’ve learned something different.
The islands.
The excursions.
The places you’ll explore when the ship docks.
But some of the best parts of a cruise happen on the days when you don’t go anywhere at all.
It’s something we didn’t understand on our first cruise, but now we plan for them.
Sea days.
At first they can feel strange.
No schedule.
No destination to explore.
Just the ship moving steadily across open water.
If you're used to busy vacations, it almost feels like you're supposed to be doing something.
But that’s the moment when the cruise actually begins to work its magic.
Sea days slow everything down.
They’re the perfect reminder that trips don’t have to be packed with plans to be meaningful.
You wake up without rushing anywhere.
Coffee lasts a little longer.
You wander instead of following a plan.
Those are the days when the ship starts to feel less like transportation and more like its own little world.
This trip reminded us of that again.
One afternoon we ended up at a wine tasting that turned into a longer conversation than we expected.
Later that evening we found ourselves back at the piano bar — which quickly became one of our favorite spots on the ship.
There’s something about live music and the rhythm of the ocean that makes the whole room relax a little.
Even the slot tournament was fun in its own ridiculous way.
We didn’t win anything impressive… unless you count finishing somewhere around 178th place.
But somehow that made it even better.
It’s the kind of silly cruise moment you laugh about later.
The highlight of one sea day, though, was dinner at Tamarind.
It’s one of the specialty restaurants on the ship, and we decided to try things we normally wouldn’t order.
Scallops.
Crispy duck.
Pineapple tapioca pudding for dessert.
Everything was incredible.
But what made the evening memorable wasn’t just the food.
It was the pace.
Dinner lasted longer.
The conversation lasted longer.
There was nowhere else we needed to be.
And that’s the real secret of sea days.
They create the same kind of space that makes travel feel like maintenance for real life.
They give you something that’s harder to find in everyday life.
Space.
Space to relax.
Space to talk.
Space to enjoy the moment you’re already in.
Ports are exciting.
But sea days are where the vacation settles in.
Where the rush of getting there fades.
Where you remember that the point of the trip wasn’t just to see new places…
It was to enjoy the time along the way.
And sometimes the best way to do that is simply letting the ocean carry you there.
Travel Isn’t Our Escape — It’s How We Maintain Our Marriage
There was a time when we thought travel was an escape.
A reward after a busy season. Something fun to look forward to when life slowed down.
But somewhere along the way, Jamie and I realized something different.
Travel isn’t our escape anymore.
It’s our maintenance plan.
Life has been busy lately. Really busy.
Work has been intense. Our house has been full. There are schedules, responsibilities, family things, and the quiet emotional weight that comes with trying to support the people you love.
None of those things are bad. In fact, many of them are the things we care about most.
But when life gets full like that, something subtle can happen in a relationship.
You start running side by side instead of actually being together.
You pass each other in the hallway.
You talk about logistics.
You solve problems.
But the space for long conversations, laughter, and noticing each other gets smaller.
That’s where travel comes in for us.
Not as an escape.
As maintenance.
When we travel, the noise of everyday life gets quieter.
There are no laundry baskets waiting.
No dishes in the sink.
No reminders popping up on our phones.
Just time.
Time to talk.
Time to wander.
Time to sit somewhere with coffee and ask each other the kinds of questions we don’t always ask at home.
Sometimes those conversations are light.
Sometimes they’re bigger ones.
Questions like:
Are we doing too much right now?
Is this pace sustainable?
What actually matters most in this season of life?
Travel creates the space for those conversations.
And honestly, those conversations are one of the most valuable parts of the trip.
Right now we’re getting excited for our upcoming cruise.
It’s not about checking destinations off a list. It’s about something much simpler.
A few days to reset.
A few days to remember what it feels like to slow down together.
A few days where we can reconnect without the constant pull of everyday responsibilities.
Over the years we’ve learned something important.
Connection doesn’t maintain itself automatically.
You have to protect it.
For us, travel is one of the ways we do that.
It’s not an escape plan.
It’s our maintenance plan.
And honestly, that realization is part of what has made us start thinking differently about the kinds of trips we want to plan in the future.
Trips that make space for connection.
Trips where people can slow down, laugh together, and remember why they like each other in the first place.
We’re even starting to explore a few ideas like that this year, including a small Reds baseball weekend in Cincinnati.
Nothing complicated. Just a fun, relaxed trip with good people.
If that kind of travel sounds like something you’d enjoy, you can join the newsletter and I’ll share details when they come together.
But whether you ever travel with us or not, I’ll leave you with the question Jamie and I ask ourselves often.
What protects connection in your busiest season?
Because whatever that thing is for you…
It’s probably worth protecting.
💛 If you enjoy thoughtful travel and connection-first trips, join the newsletter here.
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.
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.
💛 If you enjoy thoughtful travel and connection-first trips, join the newsletter here.
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?
💛 If you enjoy thoughtful travel and connection-first trips, join the newsletter here.