Lost & Found: Dan De Filippo on his Memoir 'Montauk Dayz: A Surf-Infused Retro Adventure'

Dan De Filippo thought he’d lost the manuscript of his new book, Montauk Dayz, for good.

Decades ago, as a 21-year-old adrenaline junkie with a knack for language, he set out to write his take on the American novel — an adventure in the tradition of Kerouac, Hemingway, and Wolfe. And there was no shortage of subject matter — Dan had lived hard and fast.

He met Ken Kesey and lived on the beach beneath the stars. He hitchhiked the country and saw America with his own eyes. He surfed the seas of either coast, sparking a lifelong love affair with the water.

“I had a million different jobs, surfed a million different waves,” he said of his youth. “It was a purely in-the-moment kind of existence.”

It was time, he felt, to put pen to paper, to just go for it.

And so he went.

He poured it all out in Diary of a Homeless Valet, a rip-roaring manuscript 500 pages long, chock full of sex, drugs, and strange tales of love and rebellion one scorching summer in Montauk, seen through the wide eyes of a philosopher-poet fresh out of high school.

Then he lost it.

Years passed. Dan got older.

He went to college and worked odd jobs across the country before reverting to writing, his first love. He cut his teeth at The Montauk Pioneer and joined Dan’s Papers where he became an award-winning journalist.

Then one day he turned the key in his busted Honda CRX, aimed it west. He put his foot to the pedal and drove for days and nights until the country stopped, until all that lay before him was the Pacific and its gushing waves of cyan.

He settled down in Los Angeles and wrote for The Argonaut. He chanced on a production assistant job in Hollywood after meeting a surfer in the water.

From then on, he climbed the entertainment ladder. He worked a job at the William Morris Agency for years and learned the industry’s ins and outs. He’s 49 now, owns a production company. He writes feature-length scripts and he’s won three Emmys.

‘Whatever happened to the book you were writing?’ Dan remembers his sister asking one day,  just before the pandemic.

‘It’s gone,’ he responded.

‘No it’s not,’ she replied. ‘I have a copy in my safety deposit box next to Grandma’s jewelry.’

Dan’s sister gave him the copy. Over COVID, he isolated himself — on the water, of course — and, from the deck of his sailboat anchored near his Point Lookout home, he read it through.

He rolled his eyes. He’d even yell.

But there was something there — he knew it — something buried beneath that young writer’s clutter.  So he cut and cut as waves brushed against the hull.

As he edited himself, he marveled at that boy who always was a north star, admired that spirit of adventure he’s tried to honor all his life — the child, as ever, the father of the man.

“Back then, it was ‘sleep on the beach and have a surfboard,” he recalled. “Now, it’s sleep in the house and have a mortgage. But the general tenets I was exploring back then, I’ve incorporated into the life I live now.”

So, while he had to nix the flowery language, the youthful-isms of the Diary of a Homeless Valet prose, the sentiment remained just about untouched.

He changed the title and the result, Montauk Dayz: A Surf-Infused Retro Adventure, is distinctly American, an exploration of The Dream, or something like it.

“It’s that spirit of living in this country and going for it,” Dan said of his memoir’s throughline.

He recognizes — quoting a reviewer — that the book is “like cracking open a time capsule with a poetic fist” or, plainly, an exercise of contemporary American history in the ilk of On the Road. Though set in the late ‘40s, Kerouac published the novel in ‘57 and even then it was received as something of an elegy.

Montauk Dayz is a remembrance of the 1990s, a time when he said hitchhikers could hitchhike and people could be free — not phone and Zoom and whither away.

But Dan acknowledges collective memory’s rosy-hue. He understands that nostalgia may have no real referential and the truth it venerates, be it post-war freedom in the late ’40s or pre-9/11 liberty, may well be myth.

The ramblers – Kerouac, Hemingway, and Dan De Filippo – always were the outcasts. They never were the norm.

“There’s only that small pocket of people who will do it,” he said.  “When they’re able to share those experiences with the people who don’t, the reader is doing it vicariously through them.”

“It’s like a sharing of this kind of gypsy knowledge.”

De Filippo’s debut book, Montauk Dayz, will be released June 18, 2025 by Pipeline Publishing Factory. Available on Amazon, the paperback retails for $22.99 and the Kindle version costs $9.99. Follow @montauk_dayz for more.