These Vagabond Shoes
Wednesday, April 2, 2025
We are sitting on a bench in Madison Square Park in the Flatiron District. Buildings encircle this urban oasis, framed by a blue New York sky. It is our last day in the city, and we have been walking all morning. Small dogs in fancy coats trot by us with their owners. The din of the city is somehow a comfort, like ocean surf. The temperature hovers around 30 degrees Fahrenheit, yet I feel warm in the sunlight, layered as I am in cold weather gear. Lisa sits beside me, taking it all in.
“Would you ever think of moving here permanently?” I ask. It’s a common question we pose when we travel.
“Oh, yeah,” she says without any hesitation. “I’ve always been a city girl.” Her face glows in the chilly air.
When we retired four years ago in our mid-50s, it seemed as if we had life by the tail. We sold the house and moved aboard our 43’ ocean-going trawler, set on exploring the world at a sedate six miles an hour. I’ve always loved the water, and getting this chance to cast off the bowlines was a lifelong dream. We built a home in Arizona in a 55+ retirement community as a mere precaution, a refuge from the soggy Pacific Northwest winters. Snowbirds, or maybe seagulls, might have better described us.
But a family tragedy dashed those plans. Crushed and grief-stricken, we sold the boat and stayed put in Arizona these past three years. We made friends and enjoyed the newness and comforts of a planned community that sprouted from nothing in the desert. Mostly, we worked on finding meaning in an unthinkable loss.
Over the past few months, Lisa and I started brainstorming ideas to escape the heat of these brutal Arizona summers. As someone who spent his entire life a half mile from the beach, I had no idea how scorching the desert during the height of summer could be.
These talks felt like a good sign. We were coming through it, maybe even out of it. Like Odysseus, we have traveled far. We have suffered. We have buried an oar in this place so far from the sea.
As we vetted possibilities, we knew we wanted challenge and variety, not vacation-style leisure. We needed a break from this predictable, curated life that attracts many to retirement communities.
But neither of us wanted the usual travel of flights and hotels and always being on the go. We could live out of a suitcase for a few weeks, but all summer? No. We did that during a family vacation to Europe. Forty-three stops in sixty days, including an attempt to see Paris in a weekend. Ugh. Never again.
As we pored over maps and searched travel sites, New York City kept popping up. I lived there for a year in the 1990s when Lisa and I first started dating. Neither of us could think of another U.S. city that had as much to offer a pair of healthy retirees with ample time on their hands. It would also mean a return to our very beginnings.
So, during an unseasonably warm Arizona January, we dug through our closets for winter clothes and flew to Manhattan. We walked all over the city, through Chelsea, Greenwich Village, Midtown, the Upper West and Upper East Sides, and Harlem. I heard stories that New York had changed for the worse, but in my eyes, the city was even more beautiful and clean than when I left it in 1995.
By the end of the week, we knew we had found our summer destination. We rented a furnished apartment on the Upper East Side from mid-May through mid-October. The brownstone is a half block from Central Park and not far from the five-story walk-up I rented many years ago.
We’ll have all the time we need to explore the city at our leisure, not as tourists, but as starry-eyed transplants. I’ll take writing classes. Lisa will paint. We’ll join a gym. We’ll walk the dogs twice a day through Central Park. I’ll make friends with the docents at the Met, a place I stumbled through in a daze during my only visit, but now I can study methodically.
Figuring out how to live in New York City — where to shop for groceries and how to get around on the subways — is the type of travel that, in time, will change us forever. Paris, to me now, is an irritating blur. After five months of daily life, New York will be woven into our DNA. We will always have it.
Yes, it’s a costly trip. New York is one of the most expensive cities in the world, and we splurged on a deluxe apartment. We wanted the best possible experience for this new mode of immersive travel, which might be something we repeat each summer.
“I can’t believe we rented an apartment,” Lisa says, touching my gloved hand.
“We’re doing this,” I agree.
What is this stirring I feel in my chest? Is it hope? This must be what sunrise feels to the hiker lost deep in the woods. We resume our walk, looking around as if we own the place.
