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To Hawaii: The Final Family Trip

Remembering how we always used to do this.

Petra Shepard
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VOLCANOS, Hawaii- This is it. The end of an era and a phase of life. The final big family trip.
At least while we’re still intact as a nuclear unit.

As you know, I’ve traveled the world with my wife and two girls for many years. When my first daughter was a baby we backpacked through the Dominican Republic, South America, Central America, and Mexico for a couple of years. It was just like normal travel, only with a baby. As far as travel is concerned, kids are just another piece of luggage at that point. Another piece of luggage that sometimes pukes on you and other passengers on minibuses. However, they travel well and go wherever you take them.Now, my thirteen year old is taking this lifestyle that I’ve shown her and is making it her own. She will be attending Hersey Montessori in Middle-of-nowhere, Ohio for high school. It’s a boarding school. It’s on a farm.So much for giving her access to the world by moving to the center of global culture in NYC:

I moved my family to NYC on the Fourth of July, 2019 — to the cultural center of the world. My kids go to a premium Montessori / alternative school on the Upper East Side, they hang out in Central Park every school day, they are regulars at the Met, the Museum of Natural History, and the Guggenheim, the zip all over the city exploring things that most other kids only read about in books or watch on a screen, they are set up for more opportunities per square meter than pretty much anywhere else in the world.

This is to say that I kept my end of the bargain.

However, I paid a wager that my oldest daughter doesn’t really place much value in. She isn’t impressed with the bright lights of Manhattan or the almost infinite array of international cuisine in Astoria or going to places almost daily that most people travel across the world to visit. She shrugs at the potential opportunities that come from being at the place where so many creative products are made. As far as she’s concerned, she’d be better off on a farm in ultra-rural Ohio.

I will always remember those family travels. When my second daughter came around my work was a little different. I was writing for big media, the work was sometimes intense, and I needed bases of operation to operate from. This actually fit in well with having a family. We’d make extended stops in places like Kinmen, Peneng, Johor Bahru, Sofia, Rhodes, and Prague. I would travel out from there along the spokes of the wheel and my wife would hold down the fort and concentrate on her Montessori studies.

I feel fortunate that I vlogged often during that time. Initially, it was an exercise to practice with the cameras. I was just seriously getting into filmmaking then and I needed a little training. I figured that if you can film live, uncontrolled scenarios in foreign countries as well as yourself with a camera on fully manual settings with manual focus without a flippy screen or monitor then you can film anything. That logic largely proved to be correct.

The collateral benefit of this was that I often used my wife and kids as subjects, so now I have a record to always look back on that is more in-depth, real, and nostalgic than anything I could have written or photograph. I just made these little first person narrative films about my family traveling in Asia, Oceania, and Europe and essentially memory capsuled a time of our life.

Kids are a good bellwether for the passing of time. The bigger they get the less time you have left … both with them and on this planet.

I’m halfway to Honolulu and my seven-year-old daughter is sitting next to me on the plane. She snuggles next to me and holds onto my hand. I know that in not so long she’s not going to want to hold my hand anymore. Each time it happens I know that it could be the last time.

Maybe that was the last time?



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Filed under: Hawaii, Travel Diary, Travel With Family

About the Author:

I am the founder and editor of Vagabond Journey. I’ve been traveling the world since 1999, through 91 countries. I am the author of the book, Ghost Cities of China and have written for The Guardian, Forbes, Bloomberg, The Diplomat, the South China Morning Post, and other publications. has written 3723 posts on Vagabond Journey. Contact the author.

Support VBJ’s writing on this blog:

VBJ is currently in: New York City

6 comments… add one

Leave a Comment

  • Rob June 12, 2023, 8:56 am

    It looks like you are enjoying the ‘now’, that’s a good thing! Because life is short and it does change… Aloha!

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    • VBJ June 19, 2023, 1:07 pm

      Thank you, Rob! Yes, it does change and I guess the trick is just to stay on top of the waves wherever they lead.

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  • Aroryborealis June 12, 2023, 11:24 am

    Isnt it funny being a parent? you try to do everything possible to provide the most for your kids and at some point you learn that inevitably it wasnt it. thats OK… theres no manual for us either and its totally worth them figuring out what they dont like just as mush as what they do. you grew up in ultra rural WNY where we had field parties and went to the woods to do illicit teenager things leaving you to long for the rest of the world and dare I say big cities “because they offer so much more”. Learning to let go and let them be them is tough sometimes but we all learn and grow from it.

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    • VBJ June 20, 2023, 11:38 am

      That’s all very true, Ror. They’re almost programed to want the opposite for themselves as what we set up for them. I guess that’s just part of them discovering themselves. But so funny that where we grew up the only thing we wanted was go to to NYC. We really took what we had in ultra rural WNY for granted. It took me a long time before I realized that not everyone could just jump on a bike and ride wherever they wanted, have parties in the fields, or bang chicks down by the canal. We had freedom and space to explore. You don’t have that in NYC. Maybe that’s part of why she’s pulled to a farm out in Ohio?

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  • Jack June 13, 2023, 4:05 am

    Without telling anyone, my 19 year old son grabbed a bag and hopped a plane to Canada to explore things. Mixed emotions for sure. Still processing it as I write this. It is what it is. Kids…..kids of the Vagabond.

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    • VBJ June 20, 2023, 11:34 am

      I suppose we reap what we sow. You raise a vagabond and they will leave you in the dust the first chance they get. It’s really kind of a shock when you realize that you’re the one being left. I’m the leaver … what’s going on here?

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