Tuesday · June 30, 2026 · Milos, Greece 🏝️
Homesickness While Traveling: What I Miss About Home in Midlife
A postcard from Milos. Come sit closer while I tell you what I have been missing.
Hey you, it's me. How are you?
If this were a real postcard, the front would be that impossible blue water, and the back would be far too small for everything I need to tell you. So pour your coffee and sit with me a minute.
We made it to the island of Milos, and oh, this place. Milos has a way of slowing you all the way down. My nervous system exhaled the minute we landed. Some places you visit. Some places settle your soul. Milos did that for me.
But I have to be honest with you, because that is what we do. When we first got here, I was homesick. I missed my spouse. My bed. My dogs. My own private bathroom, do not laugh. And the overthinking crept right in. Can I really walk thirty one days across Spain? Can I be gone from home that long? What is life doing back there while I am over here?
So come sit closer while I tell you what I have been missing, and how I have been getting through it. Just between us.
We landed on day one and hit the ground running. The smallest airport I have ever seen in my life. We dropped our bags and went straight to the cutest little restaurant for lunch, because I was starving.
One. My kitchen.
I have this quiet fear of not having enough to eat, of missing a meal. I do not know where it comes from. But drop me somewhere unfamiliar and it shows up and taps me on the shoulder. My own kitchen always felt like proof there would be enough.
Two. A clean restroom.
I never knew how much I took unlimited, clean restrooms for granted until I did not have them. I have had some health issues, that is a long story for another note, my friend, but let me just say I have a bladder the size of a toddler. Restrooms here are few and far between, and I have spent this whole trip scanning for the next one. But I have pushed through. The island is so beautiful it makes up for every struggle.
Three. Flat ground.
We have averaged twenty thousand steps on a slow day, and the stairs never end. Up and down, everywhere you turn. I coach so many women and men who tell me the same thing. "I'll take that trip when I retire. I'll go next year." Sweet friend, please do not wait. Europe is worth every step. Our bodies do not always give us unlimited tomorrows. If there is somewhere your heart longs to see, start making a plan. It does not have to be extravagant. It just has to begin.
Four. A real rest day.
The kind where I wake up without the energy to put on makeup, and I let that be okay. Even prepared, some mornings the tank is just empty.
I realized I didn't need to recreate home. I just needed to carry pieces of it with me. Regular FaceTime calls. Quiet moments inside local churches. Putting my phone down. Letting some memories stay off camera. Journaling the highs and lows before bed. Those simple habits have reminded me that peace is something we practice, not something we pack.
I keep thinking about my book, Silent to Spoken, and what it really means to pause. Turns out I am living the lesson now, not just writing it.
Home isn't only a place. Sometimes it's also the person you're becoming.
Ask yourself three questions:
- What do I miss most right now?
- Is there a small way I can honor that need today?
- What is one gift this place is giving me that I could not receive at home?
I still have several weeks of this journey left. The Camino will be the longest I have ever been away from home. Maybe that's what this season is really teaching me. Home isn't something I'm leaving behind. It's something I'm carrying with me. Every mile reminds me that God is just as present here as He is in my own backyard.
I'm waiting on your note~
What do you miss most about home when you travel? And what is one small way you have learned to carry pieces of it with you? Come sit closer and tell me.
Write Jenn a Note ↓Until the next postcard…
Just stay sweet out there.
I love you,
~ Jenn
P.S. I am sharing my trip in real time over on my Instagram @justjennboard. Come find the Milos edition and discover the island with me.
A Few Questions I Get Asked
The honest answers.
What causes homesickness while traveling in midlife?
For me it is the ordinary comforts I did not realize were anchoring me. My spouse. My kitchen. My own bathroom. My dogs at my feet. In midlife, home becomes less about a place and more about the routines that make my nervous system feel safe.
How do you deal with homesickness on a long trip?
I stopped trying to recreate home and started carrying pieces of it. Regular FaceTime calls. Quiet moments inside local churches. Journaling the highs and lows before bed. Peace is something we practice, not something we pack.
Is it worth traveling to Europe in midlife even with health issues?
Yes, with margin and honesty. Every step is worth it, but our bodies do not always give us unlimited tomorrows. If your heart longs to go, start making a plan. It does not have to be extravagant. It just has to begin.
What is Milos like?
Milos has a way of slowing you all the way down. My nervous system exhaled the minute we landed. Some places you visit. Some places settle your soul. Milos did that for me.
Write Jenn a Note Back
She reads every one.