The Cain family
Every trip, a new chapter.
The people, places and little moments that make up our story.
Follow our journey
2017 · The first big trip
A month. A rented van. Just the five of us.
We took a month off, rented a van, and headed west with the boys. Yosemite, Yellowstone, the Grand Canyon—and the kind of time together we wanted more of.
People called it a once-in-a-lifetime trip. We weren’t quite ready to agree.
2019 · A new member of the family
More than a way to get there.
With my parents joining our next western trip, we needed more room. So we bought a 1999 conversion van, fixed it up, and made it ours.
The Monster Van has carried a lot more than luggage. The miles, the smells, the memories—it all comes with us.
2019 · This time, bring Mom and Dad
“Once in a lifetime.” Again.
Another month out west, this time with my parents along for the ride. It meant we could share the places we loved with them—and find a few new favorites together.
Moab was one of theirs. I still remember Mom taking in the Colorado River view from Red Cliffs Lodge.
Fall 2020 · One conversation changed the school year
The road became our classroom.
Our friends Jonny and Chiara Carroll were headed to Maine. With COVID making the school year so uncertain, they suggested we homeschool and come along. We decided to give it a year.
That fall brought lobstering with Captain Clive in Maine, then Boston, New York, Philadelphia and Washington, DC. History lessons became places we could walk through together.
Winter 2021 · School first. Then the beach.
Winter looked a little different.
We spent the winter in Key West. School in the morning; the pool or the beach in the afternoon.
There were lessons at the table, afternoons outside, and plenty of reasons to think we might want to do this again.
June 2021 · A bucket-list trip, together
Taking Grandpa to the Grand Canyon.
Some trips are about a place. This one was about getting Granny and Papa there with us.
We loaded the Monster Van and headed west: four national parks, family stops, matching shirts, and a Grand Canyon visit we’re glad we didn’t keep putting off.
2021–2022 · We decided to do it again
One school year became two.
We loved that first year enough to give roadschooling another one. The Northeast called us back in the fall, and we spent the winter in San Diego.
After San Diego, my parents flew out to meet us in Phoenix. They rode home with us, with Utah and a few more stops along the way.
July 2022 · North with Chris and Pam
A little Pure Michigan.
Chris and Pam joined our family for a week in northern Michigan. We made Bellaire our base and headed out for lake days, fishing, cherry picking and Sleeping Bear Dunes.
And yes, after all those Tim Allen commercials, Michigan really did live up to the invitation.
Summer 2023 · Out west with Chris and Pam
Out west in 2023.
We took Chris and Pam, my in-laws, out west with us. In Page, Arizona, we explored slot canyons. Our photos also take us back to Moab and Yosemite.
Summer 2024 · The Home Alone house · A Twins game
On the road in 2024.
Another road trip out west. My mom and dad were with us for the Home Alone house and a Minnesota Twins game. Our photos continue through Montana, Wyoming, Colorado and the Kansas City area.
Summer 2025 · A little farther from home
Our family, across the Atlantic.
In 2025, we took the family to Europe. A different kind of trip, with the same five of us collecting the moments along the way.
Summer 2026 · Still making room for another trip
More time together. More road ahead.
This summer, my parents came out west with us again. Another chapter with the boys and their grandparents sharing the trip.
We’ve been blessed to see so much together. These are the big trips, but it’s the people—and all the little things in between—that make them ours.
There’s more along the way











