From What-If to Takeoff: A Pre-Trip Timeline

small wooden analog clock in the shape of a camera with the word "travel" next to the clock face, on a shelf
Photo by Kevin Schmid on Unsplash

Back in early 2022, we got it into our heads to embark on some serious travel.

I grew up overseas in Zambia and Botswana and traveled a decent amount when I was young. Kristen, who grew up in Seattle, had traveled a little outside the US but not beyond Western Europe.

In 2019 we took our son, Flynn, to Italy with us, and he got a kick out of it. 

Post-Italy, we could see ourselves doing a lot more traveling together.

Shortly before Covid hit, we’d also started talking about where we wanted to live longer term. There’s a lot we’d loved about living in Northampton, MA (including dear friends), but things we’d missed too. They were things that larger cities tend to offer, including less homogeneity.

Although the pandemic had put the brakes on any real planning, thoughts about where we wanted to live next continued to swirl.

In late 2021 and early 2022, that swirl of possibility condensed into something real, and big. 

Here’s how that process unfolded—slowly at first, then all of a sudden.

The December Dinner Date

The seeds of our family adventure were planted in early December 2021. Kristen and I had gone out for a dinner date. It was still the height of Covid, so we sat outside in a plastic bubble with a space heater and ate steak and drank wine.

Halfway through dinner, I broached an idea I’d been turning over in my head the previous few months. We could sell our house and take a year to travel overseas, spending anywhere from one to three months in a country, then moving on once our visas had expired.

Kristen patiently heard me out as I talked through what that trip might look like. She was a little skeptical, but receptive.

We went home, and for the next six weeks or so, the holiday season took over our focus. The travel idea, meanwhile, quietly germinated.

Saturday Turnaround to Sunday Planning

One Saturday morning in mid-January 2022, I brought up the trip idea again. This time, though, Kristen was more skeptical. 

When I reminded her that we’d likely only be able to stay in a single country for no more than three months, she expressed disappointment. (She’d either forgotten this detail, or I’d inadequately communicated it during our bubble date.) She’d been excited about the possibility of staying in one place for longer rather than hopping around.

Her enthusiasm for the trip seemed pretty much deflated. That’s the end of that plan, I thought, and we went about the rest of our Saturday. 

But as the early evening rolled around, it became clear that Kristen had been turning over the idea in her head.

“Hey,” she said. “Maybe it’d actually be pretty cool to stay in one place for a few months, then experience somewhere else.”

My ears perked up. “Yeah?”

She’d done a full 180. She was interested. A little psyched, even.

The next morning, we were both in full-on brainstorming mode. I got up and started sketching out a potential trip in a Google doc. We spent most of the day chatting and capturing ideas.

The seed had sprouted, and it was growing fast.

Spring Had Come: Gearing Up for Our Biggest Adventure

Over the next six months, we talked, researched, and slowly figured out what it would take to embark on a massive trip like this.

There was a whole lot to figure out, from how school would work, to whether or not we’d keep our house, to what would happen to our cats while we were gone.

I won’t go into a ton of detail on how those months transpired—that’s what the rest of this blog is for. 😉

But by late February we’d pretty much decided we were going to do this! In mid-March I gave four months’ notice at my job, in April we readied our house for sale, and in May we sold it. We spent the next two and a half months planning, sharing the news, and saying preparatory goodbyes.

By mid-July Kristen had left her job of 15 years. In late July, we closed on the house, packed our belongings between my parents’ basement and a storage unit, then spent two and a half weeks with family and friends before taking off for Buenos Aires, Argentina, in mid-August.

It’s mid-March as I hit “publish” on this post, and in the time that’s passed we’ve accumulated a boatload of memories and experiences.

Stick around, because there’s lots more to come.

16 Comments

  1. Nick

    Great start Ray! I look forward to the next installment!

    • Ray

      Thanks, Nick! It’s coming this Thursday!

  2. Robyn Johnson

    Thanks R asy much for the backstory for the yearlong adventure you all are now in. It was a brave and wonder full step into the known. ♥️ reading your blog.

    • Ray

      Thanks for following along. 🙂 <3

  3. Chris Hare

    I love this! The bubble date was cracking me up.

    • Ray

      As I sit here in 100-degree Chiang Mai, Thailand, the mere idea of a bubble dinner is making me sweat.

  4. This is Frank, a fellow life traveler. And this beginning is so well introduced, that I can’t wait to hear more. Thanks for letting the rest of the world in on your tres adventure!!!

    • Ray

      We’re glad you’ve joined us for the ride!

  5. Peanut

    Keep those cards and letters (posts) coming!

    • Ray

      Blogging doesn’t get us off the hook, eh? 😉

  6. Jenny

    I love learning about the first seed of Tres Adventurous- date night in a Covid bubble tent!

    • Ray

      I need to figure out how to make future retellings more dramatic. (I think we broke a wine glass too?)

  7. Can’t wait to hear more about your travels, Ray! I have so much respect that you guys had the courage to do this!

    • Ray

      Hey, thanks! We humbly appreciate it.

  8. Kathleen Winkworth

    Delighted you have started this blog, Ray. I had wondered how the seeds first got planted. Look forward to reading more of your adventures.

Comments are closed