After the initial excitement of the sabbatical and figuring out our destinations, the dream had to get real: booking flights.
Planning travel can quickly get you into red strings attached to push pins across news clippings territory if you aren’t careful. “Wait maybe we want a 10 hour layover in Istanbul!?” Here’s how to stay sane:
- Preference one-way trips and build your flights from the start of the trip to the end.
- Have no loyalty, book what works.
- Know where you can be flexible and what you have to have.
One way all the way
At first, we considered two sets of round-trip flights. One from Seattle to Pennsylvania, another from New York to somewhere in Europe, probably Brussels. Then we’d figure out one-way flights to get around Europe.
We quickly realized that wasn’t going to work. Most airlines didn’t offer much of a discount for round-trip travel. Plus, we’d likely need an extra flight in Europe just to get back to our starting point to fly home.
So, we switched our strategy entirely to one-way flights.
Since Automattic is fully remote, we have a lot of digital nomads. Someone at work suggested we try Kiwi.com’s Nomad option to plan one-way flights. The tool is pretty amazing … in theory. However, it clearly didn’t factor in kid travel. It suggested routes with over 16 hours of flying and two transfers to get to Rome. No thank you.
My go-to flight pricing tool is Skyscanner. I like the interface and the filtering options. Like all airline searches, the prices returned are for the lowest fare, which rarely works for us. Even though the prices aren’t what we are going to pay, they do present an apples to apples comparison of flights.
Convenience vs. Cost
We need to be able to pre-select our seats. Most airlines let families do this even on “saver” fares, but not always.
This brings up a consistent trade-off: convenience versus cost. The cheapest way to get to Rome from the East Coast, for example, was a Norse Atlantic Airways flight from New York.
But it left at 12:30 AM. We just couldn’t imagine getting Tom and Jerry through the airport at that hour. We’d also be fighting New York rush-hour traffic to get to the airport.
Flying at more convenient times often means more expensive flights. That’s a trade-off we’re used to making.
But sometimes, you bite the bullet. Our flight from Naples to Brussels leaves at 6:30 in the morning. We’ll be at the airport around 4:30 AM. It’s our cheapest flight by far though, and it means we didn’t have to take a train back to Rome, and probably stay overnight, just to get an affordable flight. Less transfers, more better.
So we are setting an alarm for 4:00 AM one day. Here’s how we’re going to handle that First we are staying less than a kilometer from the airport. We will be able to walk there. Wait, you are expecting a four year old to want to walk at 4:00 AM!
The Airbnb we are staying in has a projector. We are planning to curl up together on the couch and have a movie night. Hopefully everyone can fall asleep early. If not, we’ll find something sweet for breakfast. Sugar isn’t a sustainable motivator, but it can do the trick.
And we are heading to Janika’s sister-in-law. She is picking us up at the airport. No public transit, just a loving auntie. If everything goes to shit, at least we will be at her house by 11:00 AM.
This initial flight strategy laid the groundwork for our entire trip. The next post will get into the nitty-gritty of how we booked six flights from six different airports on four different airlines.
Tom and Jerry are not our boys real names. For some reason Tom got to watch Tom & Jerry in first grade, and he loves it. And for those that know me and are wondering, “Who’s Janika” I’m changing all the names.