Planes, Trains and Auto-reply

Published on: May 12, 2016

Traveling with kids on a plane? Train? Boat? Bicycle? No problem: Downtown Dad shares the many travel-with-kids tricks he’s picked up over the years, starting with giving each child several engaging responsibilities throughout the journey.

By Downtown Dad


Way back in 1997, I read Paul Terhorst’s 1988 almost-timeless-classic Cashing in on the American Dream: How to Retire at 35, which is as much a guide for dealing with families as it is a precursor for Tim Ferris’s 2007 Generation Y mantra, The 4-Hour Workweek, and all the family-friendly financial paradigms it too contains.

One concept Terhorst described was ensuring he, his wife, and daughter did not duplicate tasks and avoiding everyone having to remember the same data.

This separation of duties is not only more efficient and less confusing for all; it is significantly less noisy.

For example, whenever they arrived in a new town, he would wait with his daughter and their luggage while his wife visited several hotels to check prices. The concept being that a tired family on foot with luggage would be more likely to accept higher room rates for smaller rooms, once in the lobby. Whereas, a smartly walking lady requesting prices for a future visit would be more likely to receive offers of package deals, upgrades and promotions.

I have sworn by this technique all over ASEAN and you would be surprised what great last-minute deals one of you can get, if the rest of your party wait out of sight in the carpark or down the street a little out of earshot.

My wife and I now always split the transport and accommodation duties according to language priority, and whoever is not on that is on child supervision duty only.

So only one person at the ticket window, check-in desk, and ALWAYS only one person speaking to the waiting staff in restaurants, especially if neither of us speak the local language. This separation of duties is not only more efficient and less confusing for all; it is significantly less noisy.

Assigned duties for the kids

Expanding on this principle, our five-year-old son is now in charge of passports and tickets. This came about when baby number three was born and my wife would be holding her, while eldest son was helping me with carry-on luggage.

If children are briefed on the schedule beforehand and assigned specific tasks, the journey can be surprisingly low maintenance.

We simply did not have enough hands, so son number two would walk in front of us to the gate with five passports and boarding passes, hand them to the airline staff, wait for them to be counted back to him, and then we would count the seat rows down the aisle.

He is immensely proud of this responsibility, as is his older brother who is tasked with ad hoc bottle-feeding their little sister and carrying Daddy’s violin case through countless airports.

There really is nothing better than watching your children interact like adults when dealing with foreign customs, immigration, and transport personnel.

In 2005, on my first ever visit to Disneyland, my business partner and I walked around the Orlando venue like fish out of water vowing to only return to Disney if we were each with our own children. Within the following three years we both became fathers, Disney fans and joyous parents traveling with children.

While many people fear travel with children for various reasons, including hassle, health, and hinderance, if children are briefed on the schedule beforehand and assigned specific tasks, the journey can be surprisingly low maintenance. It should also be fun for everyone.

A dedicated travel bag for each child

Each of our children has a dedicated travel bag containing a small tin toy box to only be played when in transit and never opened at home. These boxes are kept stocked with the smallest, quaint and most interesting toys I can find when traveling overseas alone.

For example, miniature wooden train sets only six centimeters long and perfect for airline tray tables. Miniature harmonicas to play while we wait for road transport (remove these before boarding any plane as your fellow passengers will not appreciate improv bluegrass, no matter how short the flight). We have also discovered miniature airplanes made of thin balsa wood parts that come unassembled in a standard matchbox. These are all great for keeping tiny hands busy and tongues firmly stuck out the side of their mouths in deep concentration.

Systems, systems, systems

If traveling on water, we maintain the buddy system so everyone is paired with an able swimmer in case of an emergency. This goes for luggage too, so everyone knows well in advance who is responsible for each item of carry-on.

This was invaluable preparation for us last year when our boat to Koh Samet malfunctioned and all passengers were required to climb over to a substitute boat, in the middle of the sea!!!!! Luckily we all had light backpacks and the boats were firmly tied together.

He is immensely proud of this responsibility.

Nevertheless, when I was standing between two vessels with my three-month-old daughter in a front harness and helping my mother-in-law, our boys did a great job of passing handbags and impersonating any one of Harrison Ford’s characters.

Travel with bicycles was difficult with training wheels, although now we are all on two wheels and as usual with us, there is a system. Mummy or eldest son in front, everyone else in the middle and Daddy is the caboose. This allows me to speed up to the front if anyone needs help and to make sure no one gets left behind.

As much as we love long-distance train travel, this has largely been limited to mass-transit city subways in different countries, although not without fun. Once everyone has their tickets or tokens, then trusty second son is caboose and responsible for inserting Mummy or Daddy’s ticket if their hands are full.


As for AUTO-REPLY, I have never used it when traveling for business or pleasure. I just don’t think there is any point in telling people you are unavailable when they may only have to wait a couple of hours until you find a local SIM card or WiFi.

Anyway, if your work and family life are intertwined, then chances are that whoever is trying to contact you knows you travel through drop-out zones and a change of task is just as good as a holiday.


Photo courtesy of author.

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