Planning A First Family Trip

It’s become something of an annual tradition now, Every spring we try to set aside a solid week for a great vacation. The guidelines are pretty straight forward: We fly someplace that both of us haven’t been before that’s not just warm, but a little exotic.

It’s been a pretty solid streak of great vacations, last year it was Greece, and before that Portugal. Now with a 4-month old baby accompanying us, it’s added an extra element for consideration in planning this years trip.

We’ve settled on Hawaii, well Maui in Particular.
It’s modern, has all the facilities we may need and even more we probably haven’t thought we’d need. I haven’t been there before (nor has Charles 🙂 ), it’s tropical, it’s warm, there’s surfing (which must be tackled), volcanoes, culture, history, much ocean…. and the list goes on.

Seems odd to say it now, but one of the biggest factors in destination selection of this first exploratory escape has been, can we get there on a direct flight? Maui is a direct flight from Calgary, though at ~7 hrs, near the upper end of of the flight durations we were willing to tackle.

I’ve never really valued direct flights, being an airline status pursuer, flight segments (e.g. layovers) has been something that actually pays off. But now we’re seeking to get this first flight out of the way and over with as quickly as possible. We’re hoping for baby best on that flight, but prepping [mentally] for some challenges. I’m really hoping we’re not those parents with the inconsolable  screaming child that dominates the in-flight entertainment and is a fair match for all but the best noise cancelling headphones. We’ve all been there 🙁

We’ve been lucky to have had some great trips and I don’t mean to brag, but my wife and I are pretty decent vacation planners. Now as we set about planning this trip, the tectonic shift in what we consider important on a great vacation hasn’t been lost on us. In addition to planning day trips, hikes, pool/beach days,  and defining our dining hit list we’re also tackling unknowns like:

  • Where can we heat up bottles?
  • Where to buy Diapers around the hotel? Where’s the costco?
  • What brand of UPF rated clothing is the best? What UPF do we need?
  • Baby swing rentals?
  • Best place to sit on the plane with a baby
  • Hotels with kitchens?
  • How much infant formula can I bring through airport security? Can it be liquid?
  • How to tackle infant jet lag?
  • Do babies like convertibles? (joking of course)

If nothing else, this will be a learning experience for all of us. But I’m pretty confident that in additional to that, Maui will be an epic trip. Now back to more pressing things, like getting my terribly Canadian winter paled body beach ready.


A right brain Project Engineer by day, developing iOS apps by night.