A Single Dad, Two Kids, and One Messy, Beautiful Journey

I’m Jeff — a single dad and small business owner (yep, I hand-paint and sell wooden earrings that i make). I’ve changed more diapers in gas station bathrooms — and on those questionable baby-hanging stations — than I’d like to count. Over the years of traveling solo with my kids, I’ve picked up plenty of single parent travel tips, but the biggest lesson? Learning to laugh through the chaos.

This blog? It’s where I share what it’s really like to take on single parent travel — the honest, hilarious, and often chaotic version. The weird roadside attractions, the detours powered by bad directions and worse snacks, and the moments where everything goes off the rails… but still ends up kind of perfect.

I log around 40,000 miles a year for work, which means I’m constantly on the road — a lifestyle that makes me something of an expert in single parent travel. So when it’s time for a break with the kids, what do we do? You guessed it — we hit the road again.

Over the years, travel has become more than just a getaway — it’s been a way to reconnect with my kids, reset after hard stretches, and remind ourselves that joy still fits in the carry-on.

So if you’re a single parent looking for travel ideas, encouragement, or just proof that other people screw up the GPS too — Apple Maps has a personal vendetta, I swear — you’re in the right place.

Seriously — welcome to the chaos. Let’s figure this out together.

Why We’re Here

Life changes — and so do we. After years on the road as a full-time vendor, working festivals, comic cons, and pop-ups across the country, I’ve experienced unforgettable moments and met amazing people. But lately, I’ve felt the need to slow down and shift gears.

I’m stepping into something new: part-time travel advisor, part-time vendor, and full-time dad trying to figure it all out. I want a life that gives me more time with my kids, more space to show up for the people I love, and maybe — just maybe — a chance to start dating again (somewhere besides a comic con booth).

This blog is part of that transition. A place to share the journey — the wins, the pivots, and the questions I’m still working through.

If you’re in the middle of figuring things out — trying something new, shifting gears, or just trying to make life work — you’re not alone. I’m learning as I go — probably the hard way.

What You’ll Find Here

We’re not influencers. We’re not luxury travelers. We don’t even own matching luggage. But we are real. Here’s what you’ll see on this blog:

• Family travel tips from a single parent’s POV
• Honest stories about parenting on the go
• Budget-friendly road trip ideas with kids
• Festival recaps from behind the vendor booth
• The messy stuff that makes the memories matter

Whether you’re co-parenting, solo parenting, or just trying to survive a three-hour drive without someone crying (it’s usually me), there’s a seat for you at our table. You’ll find family travel advice, honest stories, and plenty of single parent travel tips to help make your next trip easier.

Making It Count

This isn’t about having the perfect vacation.

It’s about making time — even when life’s messy. It’s about connecting when it feels easier to just hand over the tablet. It’s about choosing the trip over the trap of routine, even if the hotel pool smells like regret.

Because these are the moments we’ll remember — the messy, unforgettable ones that turn into inside jokes or unexpected joy.

And because Winkler, Party of Three isn’t just our name — it’s our invitation to make every journey feel like a celebration. We’re more than just a family team; we’re the kind of crew that makes fun out of whatever’s in front of us — whether it’s a forest fire in Oregon, a rest stop, or a rainy day in a tiny motel room in Midland, TX.

One trip, one detour, one miracle at a time.

Join the Ride

If you’re a single parent figuring out how to make travel work, someone looking for travel advice, or just a parent trying to make the most of the precious little time you get with your kids — welcome. We’re building a single parent travel community that gets it.

Share your stories with us. Have a road trip win, a hilarious fail, or a meltdown that turned into a memory? Drop a comment or send a message.

I don’t have all the answers. I’m figuring this out right alongside you. This blog isn’t just about sharing what works. It’s about asking questions, trying things, and learning as we go. I’d love to hear what travel looks like for you.

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