Here's mine.


The Judi Ann

A 30-foot Pearson Wanderer. Named after my mother. My parents bought her when I was young and she was the backdrop to most of my childhood — Montauk, Block Island, Fire Island, weekends on the hook, learning to read wind and tide before I knew how to read a map. She smelled like teak oil and salt. She made the ocean feel like home.

My sister stepped aboard my current boat recently for the first time and said it reminded her of the Judi Ann. I didn't say anything. I just nodded.

Some things you don't need to explain.


The K2

A 13-foot Boston Whaler fixer-upper. The family bought her as a project — beat up, cheap, full of potential. We named her K2 after the mountain, because I've always loved the mountains as much as the sea, and because she was "Keith's Too."

K2 is the second-hardest mountain in the world to summit. More dangerous than Everest. A higher death rate. We named a beat-up Boston Whaler after it.

That probably tells you something about how I was raised.


The Plan B

COVID. The marriage was still intact, or something that looked like it. We bought a boat together — me and my wife — because the world had shut down and we needed something to do and somewhere to be. Her mother helped finance it.

We named it Plan B.

There's another layer to that name worth knowing. Plan B is also a parenting methodology — a specific approach to raising kids on the autism spectrum. Collaborative problem-solving rather than imposing solutions. Meeting the child where they are instead of where you want them to be. Two of our four kids have autism. Plan B wasn't just the name of a boat. It was the name of how we were trying to parent.

I thought the name was ironic at the time. In retrospect it was a diagnosis.

When the divorce came through, the Plan B was sold to pay back what we owed. That felt right. You can't keep a boat named Plan B when you're trying to build something.


The Nomad

Not mine. A friend's boat, in Santa Cruz. I was between everything — between coasts, between relationships, between versions of myself — and a friend let me live aboard while I figured out what came next. I was looking for a boat to buy in California. The deal I thought I had fell through.

I didn't name the Nomad. But I lived on her for a while, and the name fit. That was the drifting chapter. That was the between.


The Lost and Found

Her previous name was Sarah Abby III. She was built in 1984. A Mason 43 — the exact boat my wife and I dreamed about buying together when we were in our late twenties, before the kids, before Grenada, before any of it. We never got her then.

I found her in Rock Hall, Maryland. My parents pulled money from their savings for the down payment. I flew in to see her, walked the deck, put my hands on the wheel, and knew.

When I wrote the letter to her previous owner — a man named David — I tried to explain the name. "The Lost & Found is marking a journey of my own wandering near and far: professionally, romantically and in world travels as a surfer and entrepreneur. Here, on the Sarah Abby III, I truly feel I've found what I've been looking for."

I've wanted a Mason 43 since my twenties. I'm 45 now. The timing is not lost on me.

They also tell me she was the boat used in the filming of Romancing the Stone. I cannot confirm this. But I choose to believe it. It fits.


Judi Ann. K2. Plan B. Nomad. Lost and Found.

Named after my mother. Named after a mountain. Named after a backup plan that wasn't. Named after drifting. Named after finally finding.

That's the autobiography. Five boats, one life.

The morning always comes. And so does the next vessel.