If You Could Go Anywhere…

Sometimes the best destination isn't the one you planned.

On Christmas Day, I gave my wife, Gina, tickets to see Def Leppard in Las Vegas. Flights, hotel—everything was already arranged. As we talked about our upcoming trips, my 79-year-old mother-in-law, Janet, smiled and commented that we always seemed to be heading off on another adventure.

"It must be nice," she said, with zero jealousy in her voice—she was genuinely happy for us.

I'd asked her before, but this time I asked again: "If you could go anywhere, see anything, or do anything, what would you choose?"

She didn't hesitate. "I've always wanted to see the Chincoteague Pony Swim."

As a little girl, she'd read Misty of Chincoteague. She'd owned a horse when she was young, and that dream had quietly stayed with her for decades. Before Christmas Day was over, I'd rented a house for a week in Chincoteague, Virginia.

"Don't worry about reservations, directions, or any of the planning," I told her. "I've got it. Just be at our house on departure day."

Crossing the Bay

The drive north was part of the adventure, but something shifted when we crossed the Chesapeake Bay Bridge-Tunnel. The traffic faded, the pace slowed, and it felt like we’d left everyday life behind.

When we crossed onto Chincoteague Island, Janet grew quiet. After a few minutes, she looked out the window and simply said, "It's beautiful."

That's when I knew this wasn't just another vacation.

The next morning at the South Corral on Assateague Island, I expected Janet to spend the time watching horses. Instead, I found myself watching her. She talked with volunteers, struck up conversations with complete strangers, and laughed with people who shared her lifelong love of horses. She wasn't standing on the sidelines—she was fully part of it.

The Pony Swim itself was hot, crowded, and wonderful. By the afternoon, we were exhausted and walking back toward our rental when we met Francine, a local stranger who invited us onto her porch, offered us water, and drove me back to get our car. We'll probably never see Francine again, but she’ll always be part of our Chincoteague story.

One of my favorite photographs from the trip isn't of a pony. It's of Janet pretending to do an oyster shooter while taking a sip of my Bloody Mary—completely out of character, but simply happy enough to play along.

The Real Reason for the Trip

Later that week, Janet told us that as much as she enjoyed seeing the ponies, the conversations she had with people all week meant even more. That stopped me. I thought we'd driven more than 700 miles so she could see the famous Pony Swim. Instead, she’d found something she didn't even know she was missing: connection.

It wasn't until we got home that I fully understood why this trip had become so important to me.

Over the previous year, I lost my stepmother to Alzheimer's. A few months later, my father suffered a devastating stroke—just after telling me he wanted to travel, reconnect with family, and live out his plans. Around that same time, I lost a close friend in an accident at age 63, while he was still looking forward to retirement.

Time had other plans for them.

Those losses changed the way I think about travel. When I look at someone I love who is 79 years old, I don't see a number. I see precious time.

I don't want her tomorrows filled with "I wish I had..." I want them filled with laughter, conversations, pretending to eat an oyster, and making stories.

We drove over 700 miles to see the ponies, yes. But what I really wanted was to give someone I love another week of living—instead of simply letting another week pass by.

Because none of us knows how many tomorrows we have left.