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Relay: Sail Inn, Sail On

Wed, 10/26/2022 - 18:40

The Sail Inn in Montauk’s fishing village was my home in the winter of 1997-’98, and so it was with a bit of wistful mirth that I saw that the owner George Galway is retiring and the place is or will be closing shortly, awaiting a new operator.

My father leased the Sail Inn from Mr. Galway for about a decade in the last century, and in doing so, drove himself to an early death for ignoring Rule #1 of bar ownership: You can’t be the best customer in your own saloon.

Still, I always supported my father’s midlife decision to bail out on the corporate life and move to Montauk. Here was a man who lost both his parents, his wife, and one of his sisters during a particularly bad stretch in my family history — and never recovered from the trauma of those people dying within a few years of each other in the late 1970s and early 1980s. 

That his children had lost their grandparents, their mother, and their aunt never registered with the old man, who had a bit of a narcissistic side to go along with the alcoholic angry-sad man routine.

Bars are full of people like my late father, who referred to himself as a “social alcoholic,” and who spent his bar life seeking the kind of solace in loneliness that only a flatly weird and off-the-drag bar like the Sail Inn could provide — at once homey, comfortable, and insular. 

My father was a lot of things but a “dad” was not one of them. He was a father, he was the “old man,” he was “pops,” and he was occasionally “Kenny” — but the whole “dad” part of parenting was never his thing.

I always hoped it would be. I arrived at the Sail Inn in late August of 1997 with some hopes of getting closer to the old man. He’d been running the motel for several years by that point and was well on his way to drinking himself to death.

I was living UpIsland in Long Beach and had worked the previous couple of years at a music magazine in Manhattan, after nearly getting murdered by a shiv-wielding maniac in Brooklyn in 1995.

That was a life-changing event that took place while my father and I weren’t speaking, but he did show up at the hospital after the mugging, and we again tried to make a go of a proper father-son relationship.

After a couple years at the music magazine I was restless and sick of the city. I had always wanted to hike around the entire perimeter of Long Island, so I quit the job abruptly, strapped on a backpack, walked out the door of the oceanfront apartment, and headed east along the beach.

Six nights later I was on the beach in East Hampton unable to find a place to camp safe from The Law. I hiked in twilight awhile before I spied a large and seemingly open space between the beach and homes. I scurried into this area as darkness fell, set up camp out of sight of the beach, and conked out almost immediately.

I woke to the sound of a lawn mower and peered out in the dewy morning from my sandy nook. A Latino guy was trimming the nearby grass.

Except it wasn’t just any grass, as I later learned. It was a putting green at the Maidstone Club. I had apparently and inadvertently camped out in an adjacent sand trap.

The guy gave me a look that said, “I don’t even want to know,” and got back to cutting the grass. I quickly gathered up my gear and proceeded with the journey. Next stop: The Sail Inn.

Hours later I arrived at Kirk Park in Montauk and called for a Pink Tuna cab to take me to the old man’s place. The motel was sold out for Labor Day weekend and the bar was hopping with activity and laughs. I pitched my tent and joined in.

It was my 30th birthday.

The late Kathy Surrey was behind the taps, and when I told her where I’d camped the night before, she burst out laughing and said I’d pitched tent at one of the most exclusive country clubs in the world. “They shoot people for doing stuff like that,” Kathy said before telling the whole bar about my outlaw camping adventure — I gracefully accepted grudging props from the gathered locals.

A couple days later I was preparing the next leg of the hike, which would take me to Montauk Point, when my father uttered some fateful words: “I could use your help around here. Think you could stick around a little longer?”

How could I say no? I stuck around and got into the swing of things, the daily ritual of coffee and the morning news above the bar on TV followed seamlessly by the first beer of the day. I’d help when it was time to tote up a keg from the basement, I trimmed the Montauk daisies, did some general repairs, and worked as a “chamberlad,” cleaning rooms for guests.

I had a room upstairs and a trickle of freelance writing work that winter, too, but it was a downward financial spiral for both father and son, with booze as the backdrop.

That winter at the Sail Inn did provide a fleeting sense of security, of grounding, of being at home, of at last being a son who had a dad. I got to know the old man a little better over those bleak winter months, and he’d break my heart just a little bit more every night when he’d fall asleep at the bar with a Dewar’s in front of him.

He always warned me to not get caught up in the romance of Montauk — it had been his downfall — but how could I not?

One day I worked the taps and marveled at how I’d come to know everyone at the bar — by their nicknames only. There was Sarge, the late handyman, who was always handy with a scraggly roach in the breezeway, and there was Victor the Norwegian, Slow Bob, Ritchie the Bum, T-Bone, Coon, Flip-Flop, Sid the Squid, and the legendary Joey Flapjaws.

Not long after — it seems like an eternity — I was back in the city in the spring of 2002, six months removed from 9/11, and again feeling restless and sick of the city. One day I scoured the East Hampton Star help-wanted section and secured an interview at the Montauk Point Lighthouse.

My father had left Montauk by then, after losing his house, his boat, and his health. He drove me to the interview but warned me against moving to Montauk. It was too late for that.

I found a seasonal place near the docks, and, thanks to those Sail Inn connections, bullshitted my way into a job on the Marlin V. I went on to spend four seasons in Montauk, wrote a novel about it, worked deck on party boats, did some commercial lobstering, and became a generally abrasive if not-unfriendly presence in the bars. 

For better and worse, none of that would have happened were it not for the old man.


Tom Gogola is a reporter at The Star.


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