20 Questions You Should Ask Traveling Dads

IMPRESS YOUR GUESTS WITH DAD FAVORITES (BEYOND A BBQ GRILL)

Impress your Airbnb guests with Dad favorites like the Z Grill and beyond

Have You Wondered

“What makes a traveling dad happy?”

It’s entirely possible that you’ve never wondered, “What makes a traveling dad happy?” to increase bookings. It’s easy for hosts to focus on marketing to the mamas, because they’re the parents so often booking the stay…but, have you considered that when dad is in the house, he’s often the one putting out the fires and backing the reviews?

As Father’s Day approaches, we celebrate the fathers who show up every day for our families. How can we show up for them? HOW CAN WE CAPTURE THEIR ATTENTION?

As hosts, your job is to serve every guest. Yes, a lot of dads love to barbecue, so equip your rental with a stellar grill (like the Z Grill pellet smoker featured above)…But there’s so much more to these men, and you should be putting weight on an experience they’ll rave about. So, I wanted to ask dads a few questions about fatherhood adventures, travel preferences and favorites. Turns out, I live and work with one.

If you’ve been following The Olive Jar, you’ve met Jeff, but probably don’t know it. He’s usually behind the camera or in his edit bay, producing all that juicy media content for our STR clients.

Jeff is father to our two beautiful girls, Sicily and Eva. We’ve been married for 16 years, parents for almost 10 of those. We’re getting old, y’all, so here comes a game of 20 questions covering the past, present and future.

If you serve traveling families, let these questions spark your own research on the traveling dads you host. Knowing their passions and preferences will inform the way you show up for traveling dads and their families every day.

Without further ado, meet Jeff AND OUR LITTLE FAMILY UNIT

20 QUESTIONS FOR DADS:

EXPLORE THE PAST, PRESENT AND FUTURE


MEMORIES: WHEN WE WERE YOUNG

Q1: When you were a kid, what did you want to be when you grew up?

A marine biologist. Who didn’t right?! I think it’s mainly because I liked dolphins…and exploring the unknown.

Q2: Before we had our first kid, what was your biggest question about fatherhood?

How in the world will I be able to raise a kid? Will I be good at it? I think other people have it together, and I’m going to be the failure as a dad. I quickly learned no one really knows what they’re doing. I can read a book, but it wasn’t until I was in it, that I began to grow into this new side of me.

Q3: When we were pregnant with our second, what was your next biggest question about fatherhood?

Same questions, ha! Times two. Now how do I be at two places at once? Like will I neglect one kiddo because I’m focused on the other? It was man-on-man coverage (to use a football term), but soon figured out I don’t have to be in two places at once. I take solo time with each of them, intentional to give them each their own special adventures. That one-on-one quality time is powerful. Somehow, it makes us stronger as a family unit.

Q4: What drove you crazy in the early days? What drove you to be a better dad?

I look back at pandemic times…Eva had just turned 1 year old the week before shut down, and Sicily was 5. Tt was definitely maddening to feel trapped in our house. The constant proximity was too much. We took tons of walks in a quiet part of our neighborhood. That change of scenery was a reset to reconnect every time. It got tougher when there were massive forest fires above us in Angeles Forest. The smoke was so thick we were actually forced to remain inside. We had to tape up the cracks between the doors and windows of our old craftsman home, and close off our fireplace. Being stuck like that definitely forced me to dig deep, reflect on how I had be more patient. If I couldn’t do that, I wasn’t going to make it as the dad they needed most. In practice, that looked like taking time early in the morning to journal and meditate. Then at night connecting with my wife and, honestly, taking a brain break a good show or movie.

Q5: What’s a travel memory with our girls in their youngest years that you still think about today?

I think for both girls, it was hiking with them on my back in a hand-me-down backpack carrier. The thing wasn’t in great shape, it squeaked—and girls seemed to get heavier and heavier as I got older and older. On every hike, both girls (when around 2 or 3 years old) would always pass out minutes into the journey. And their little head would just bob back-and-forth as I trudged up a mountain-side. Then as hikers would pass, they’d smile, commenting how cute our little lady was. Those hikes were worth the heavy lifting, wouldn’t have been the same without the girls.


PRESENT DAY TRAVEL:

Sicily IS 9 YEARS OLD, Eva is 5, AND WE’RE IN OUR 40’S


Q6: What does a perfect weekend away look like with our kids? (Is perfect even real?)

It is difficult for sure! We were told a long time ago that with kids, just call it a “trip,” not a vacation. That isn’t to say we can’t have fun but it’s setting our expectations of what we can accomplish. That said, a weekend away with a pool and some sort of adventure (hiking, bikes, etc) is all it takes. Now that our girls are older, we can venture out for more challenging hikes, climb to higher heights.

Q7: We love hiking, Sicily loves hiking, Eva has a love-hate relationship with hiking. What’s your trick to keep Eva going on the trail?

Mainly it’s just letting her be her. Let her take the pace she needs and not have expectations of what the hike “should” look like. And of course being willing to pick her up when she can’t take it anymore. “Uppy daddy!”

Q8: What kind of excursions do you like taking Sicily on?

We all bring our bikes when we drive to Yosemite or out to Sedona, but it’s great quality time when it’s just her and me. She’ll call out “woo hoo!” at a fun bump or turn, just like she did when she first started riding. I love that she gets to explore new places we couldn’t reach by just hiking, too.

Q9: What helps makes family meals most memorable on vacation?

Whether it’s in a vacation rental or at a restaurant, it’s playing games together. We love “Heads Up” for Kids on the iPhone or “Spot-It” card game. We try to bring small things that can keep us all engaged.

Q10: Describe the perfect vacation nap.

Hammock in the shade or a plush leather recliner in a quiet room in the back of the house—that’s the best. Something secluded (where the kids can’t reach me, ha) that takes me to another place. Oh, and, a baseball cap pulled over my eyes, always.

Q11: Your favorite road trip playlists include bands and artists like…

Johnny Cash, Willie Nelson, or John Denver. There’s an earnestness and longing in their music that feels so right for seeking adventure.

Q12: Your camera is always rolling. What moments do you rewatch the most?

Pizza. J/k. I love seeing my kids laugh. So whether it’s on an adventure or a simple dinner out, I love scrolling through my photos (or catching Apple pop-up an old memory) to re-find our family simply laughing together. Hearing my wife and kids giggle, or just seeing their smiling faces, brings a big smile to mine.

 

VACATION RENTAL PREFERENCES: DAD FAVORITES

Q13: What do you look forward to most staying in a vacation rental?

The surprise layers of design and amenities make me feel seen and understood. I look forward to an explore guide that sets us up for a successful trip—not a big book of do’s and don’ts. For sure I’ve done my own planning, but when I find a little gem in the guidebook that I haven’t found anywhere else, that gets me excited.

Q14: What are the top family activities and amenities we don’t have at home, but you 100% look for in a vacation rental?

Water features—I love a good hot tub or pool. It’s almost always #1 on our list when looking for a place to stay; a dedicated room for board games and video games is always a fun surprise; and even though we do have vinyl records at home, I love to come into a space and discover their own unique collection.

Q15: In our house, you make us the best breakfasts. What’s one chef’s kitchen tool or appliance you would love to see in the next STR we book?

Thanks, I’m flattered, ha. A crepe pan would be amazing. Maybe a waffle maker. But if we’re talking basics too, I always need a great non-stick skillet for the best scrambled eggs.

Q16: How can vacation rental hosts better serve Dads?

On-site babysitting!? But for real, local babysitter recs. Beyond that, it always comes back to a perfect place to relax—like a hammock or cozy arm chair I can sink into…while I drink an old fashioned and read Hemingway.

Q17: You do a lot of the heavy lifting in the check out process, and it can be chaos with kids. How can hosts make that easier for you?

Less is more. I get that there is always a ton to do for the cleaners, but whatever makes the experience simple and clear, that’s worth its weight in check-out guides.

THE FUTURE: WHAT’S SO BRIGHT?

Q18: What’s next on your big dream family travel bucket list? (I’m taking notes)

Would love to finally get the girls to Italy or New Zealand, but within the country, it’s an Airstream trek around the country for a month.

Q19: What do you want to be when you grow up? As in, a retired old man.

Rally car racer! Have no idea how to do it, but put me in a blue WRX with a stick shift, and I’ll figure it out.

Q20: What do you hope our kids remember most about our family adventures?

That no matter where we are, what matters most are the experiences we create and the people we get to create them with.


MEET “Olive Jar JEFF”

Okay so you’re finally seeing his face in this blog post—but like I said, he works so hard behind the camera (and in post). Tap below for a glimpse of Blue Skies, a luxury vacation rental in Oceanside, California you should book. It’s just one of many properties Jeff has captured in motion. I’m so proud to have Jeff as an Olive Jar partner, serving hosts together every day!

HOW ARE YOU SHOWING UP FOR DADS?

The questions I posed were customized for the traveling dad I want to know better. Hope there were a handful that peaked your curiosity. What are some questions you’d like to know about the traveling dads you’re hosting? We’ll help you find the answers.