Hampton Style - June 27, 2008 - The Boys of the Endless Summer

If you'd like to spot an original Montauk landmark in his natural habitat, just after dawn pull into what locals call the "dirt lot"-a tucked-away parking space that abuts one of the wave breaks along the surfing mecca that is Ditch Plains-and there at the end will be a solitary, white-haired man watching the ocean. Standing on a dusty outcrop, eyes keenly scanning out past the shore for real waves and signs of potential ones, will be riding legend and retired pro-surfer Tony Caramanico, the lone surf sentry.

Amid the diehard surfing fraternity of salt-washed Montauk, Caramanico is a legendary force of nature. A title-winning surfer across five decades (his first win was in 1969), Tony resurged as a nose-riding master in the early '90s after longboarding regained popularity, and is now an esteemed surfing teacher, artist and board designer. He serves as an elder statesman for the Montauk surfing veterans, as well as Zen master to a new school of up-and-comers. Caramanico is a cultural rarity-not only did he manage to revive a pro-surfing career in his 40s, he also never had to shelve his passion for traveling and the sport to hold down a day job; he merely shifted focus so that surfing has sustained him his whole life.

"I was sponsored as a kid, rode in teams and competitions, but there was no money in it then. No pro-surfers. You did it for a board, maybe a bit of merchandise they'd throw you; you had to be smart and reinvent if you wanted to keep going. I owned my first surf shop at 20. Now sponsors throw money at kids from the time they're in the water, just in case they're exceptional; most of them are washed up by the time they're 21. There's a girl from Montauk who has a $50,000-plus sponsorship deal; she's 12. I was just a kid who wanted to ride waves. The excitement never wore out and I turn 58 next week," says Caramanico.

"Surfing has always drawn artistic and creative people, and out here, the Hamptons and Montauk, has always been a gathering place for artists. Surfers are from the same cut, they're adventurers, and they seek out beautiful places like this," he says.

Despite the raw edges of Ditch Plains, it is beautiful as dawn breaks on the beach one joltingly early summer morning when I joined Tony at the surfing break known as "trailer park." The swiftly rising sun filtered rays over a neat row of namesake trailers up on the bluff and along the jutting Montauk cliff face. This is what people refer to as "up with the birds" (half an hour before dawn), or as they call it in Bali, Caramanico tells me, "first chicken." When it comes to dawn patrol among the grass-roots surfers of Montauk, Tony is first chicken.

In his surfing hoodie, colored Vans and silver porn-star mustache, Tony is an eye-catcher on the sand. Think Sam Elliott mixed with the Ancient Mariner. He is sprightly, with a younger man's physicality. Surfing has kept him limber, curious and enthusiastic; a life spent in the sun and salt water has not worn this man. Even at this ungodly hour, Caramanico is twitching with energy. Following a wild electrical storm the night before, the surf this morning is flatter than he'd hoped, but it shows promise, so he heads home, up the hill to the rickety hamlet that is Montauk's original main village, to collect his boards.

Just after 6:30 a.m., two of Montauk's resident band of brothers roll into the parking lot. One is local surfer and musician Jimmy Buffett. Not easy to miss in his subtle new ride, a forest service-green Scooby-Doo van, Buffett pulls in grinning as a handful of comrades gather to gawk at the ultimate in solar-paneled, vegetable oil-fueled eco-cruising. Buffett maintains an enigmatic smile, unpacking his boards while sightseeing friends tour the van's carpeted, cream interior. "How much is Crisco a gallon?" and "Do you smell French fries when you're driving?" are just a few of the inquiries thrown his way.