32 COUNTRIES ● 5 CONTINENTS ● ONE LIFETIME

Trips that separate
“We wish we had" from
"We’re so glad we did."

We're Erin and Matt, working through a list of places
we'd regret never seeing. Someday is now.

EXPLORE OUR ADVENTURES

THE STORY BEHIND THE NAME

What, Exactly, is a
Lifetime Pity?

China, 2005. Newly married, early 20s, and way out of our comfort zone on our first guided tour. When the bus pulled up to the Great Wall, I looked out the window at what seemed like a million stairs going straight up a mountain.

Our guide Michael stood at the front and said something we've never forgotten: "You don't have to climb. But this is a lifetime pity…You will regret your whole life not being on the Great Wall.“

A lifetime pity. The phrase hit us both. This wasn't just about the Great Wall. This was about every place we'd ever dreamed of seeing. Every experience we might look back on and think, “We wish we had...”

That's what we've called them ever since. And here's the thing: your list never gets shorter. You cross one off, you add three more. It's this beautiful, never-ending thing.

Straight from the Camera

I tell you what happened. Matt shows you what it looked like.

He shoots it and leaves it alone. No filters, no cranking a sunset until it looks like a screensaver.
Some of these go back 25 years on his first Minolta X-700 35mm camera, long the before the digital era.

WHAT'S NEXT

Currently
Crossing Off

Not every trip is a far-flung adventure. Some are just places that have lived rent-free in our heads for years. Here's what we're chipping away at.

✓
Finnish Lapland - Reindeer, Husky sled rides, and winter magic
✓ Feb 2026
✓
Medinas of Morocco - Rabat, Chefchaouen, Fes, Ait Ben Haddou, and Marrakech
✓ Apr 2026
✓
Basque Region, Spain - Filling our bellies through the Pyrénées to San Sebastián
✓ July 2026
✓
Faroe Islands - Exploring grass-roofed villages, dramatic sea cliffs, and cascading waterfalls
✓ September 2026
Vietnam - Bustling streets, glowing lanterns, misty mountains, and tiered rice fields
📍 February 2027
Crossed Off
Up Next