On an end-of-season afternoon, one of those days when the sun feels blazing hot, The Dock at Crayton Cove’s brick courtyard is full of people. A steady stream of ladies in flowy blouses and families with hair still tousled from the beach add their names to the list for a table. “Believe it or not, this is a slow day,” the hostess tells me during a momentary lull. At golden hour, waits can swell to two hours. Regulars and tourists alike wait for prime waterfront seats to watch the boats bobbing in Naples Bay. Ceiling fans spin languidly under lacquered wood ceilings, pushing the warm, salty breeze through the open-air dining room. Fat fillets of grouper bathed in Key lime butter and cocktails beaded with condensation are in constant rotation. Where walls exist, they’re hung with vintage photos showing people in disco-era micro shorts cracking open beers and cheering as teams race canoes across the bay.
the dock crayton 50 years cove old party photo
Courtesy The Dock at Crayton Cove
The Dock is a living relic of a vanishing Naples. Opened in 1976, when the street outside the restaurant was an unpaved path of crushed shells, it became an immediate sensation and a defining part of the city’s social scene. Longtime Neapolitans talk about those early decades with almost mythic reverence—the parties, the people, the water and the wood.
In 2019, founder Vin DePasquale retired after more than 40 years. He sold the restaurant to longtime friend Doug Traina and his son, Dan Groom-Traina. The exchange came with a promise that the new stewards would uphold the restaurant’s legacy while guiding its next chapter. “The Dock is a feeling. It’s a timeless place that has real culture and history,” Dan says. “If you were given four blank walls and an unlimited budget, you couldn’t replicate that.”
Though it’s now an institution, The Dock started as a side project. In the early ’70s, Vin, Kenney Schryver and Chuck Bruce partnered to develop the preexisting Cove Inn into condominiums and open a private members’ club on Crayton Cove. Vin proposed turning an adjacent, flat-roof office building into a casual, alfresco seafood restaurant.
Photography by Brian Tietz
Photography by Brian Tietz
Photography by Brian Tietz
Photography by Brian Tietz
They built the restaurant plank by plank, enlisting boatbuilders from the marina to seal the centerpiece bar with waterproof resin. Smudge pots borrowed from nearby farms warmed the room so it could set. Naples artist Jerry Vallez painted the exterior in a faux-wood finish and built bar lamps from liquor bottles. Flattened, painted tomato crates became the first tables, and a patch of grass along the sandy shore was treated as a makeshift patio, with cypress stumps to support cocktails and fringed Cinzano umbrellas.
The Dock opened on a Friday in February to a line of 200 people. “We were months behind with opening,” says Tom Jennings, the original general manager, who later founded The Bay House in North Naples. “Everybody knew something was happening there. It built up the enthusiasm.”
Handwritten chalkboard menus listed oysters, clams, shrimp, conch, a corned beef sandwich and the signature New England-style Dock chowder. The kitchen wasn’t operational, so employees would haul the food over from the club next door.
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Photography by Brian Tietz
the dock crayton 50 years cove dining room and bar
The Dock has been a gathering place for Neapolitans and visitors since 1976. Its wood-paneled walls stand as testaments to the area’s rich history: Weathered ores and photos nod to the birthplace of The Great Dock Canoe Race.
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Photography by Brian Tietz
the dock crayton 50 years cove outdoor dining room
The Dock quickly became known for its laid-back party culture. “We were a bunch of 20- and 30-year-olds who were best friends and made sure the locals had a good time,” says Deedee Brown, who worked at the restaurant from 1976 until 2019. That spirit spilled into everything. From its earliest days, bartenders turned shifts into stand-up comedy shows. Festivities marked nearly every holiday from Halloween to an annual Dickens-themed Christmas dinner. In the slow season, they brought in steel drum bands and pushed the tables aside to make a dance floor. After the first Naples St. Patrick’s Day Parade in 1976, the event founders held a spontaneous sing-along that filled The Dock past capacity.
No idea was too outrageous, and one in particular took on a life of its own: The Great Dock Canoe Race. First held in 1977, it charted a course between The Dock and the Riverwalk, a restaurant Vin and Kenney had opened at their new development, Tin City. The race—which ended in 2019 and has been revived in a new iteration at Baker Park with new organizers—drew as many as 10,000 spectators at its peak.
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Courtesy The Dock at Crayton Cove
the dock crayton 50 years cove vin pasquale
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Courtesy The Dock at Crayton Cove
the dock crayton 50 years cove old canoe race photos
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Courtesy The Dock at Crayton Cove
the dock crayton 50 years cove old canoe race photos
From his perch at the bar, Vin watched a new Naples arrive. The completion of I-75 and Southwest Florida International Airport delivered a steady stream of retiring corporate executives, while new gated golf communities and beachfront high-rises rose to house them. Vin quietly polished the restaurant’s edges to match his evolving clientele, but kept the unpretentious, dockside vibe. He expanded the menu, adding modern plates with tropical flair to the battery of fried seafood. A new bloody mary bar at brunch was as close to a viral moment as you could have in a pre-social media ’90s, with all kinds of garnishes, from half a dozen types of stuffed olives to pickled okra and shellfish. “We were constantly moving forward, updating the uniforms, the dinnerware, the seating,” Deedee says.
With its waterfront views and open-air dining room unchanged, The Dock continued to thrive even as other iconic restaurants of the era, like Truffles and St. George and the Dragon, closed. Over the years, Vin rebuffed offers from buyers interested in the increasingly valuable property along Crayton Cove, protective of both the restaurant and what it represented. When Doug and Dan approached him in 2019, Vin, who was in his mid-70s, recognized the restaurant would eventually need new stewardship. “I’m still not ready … because this is a passionate business for me with longtime relationships,” Vin told Gulfshore Life at the time of the sale. “But Doug has a similar passion to keep this restaurant exactly as it is … The vision we had was the same.”
Not long after the sale, the new owners faced their first major test when Hurricane Ian tore through Southwest Florida in 2022. The Dock had weathered major storms—Irma ripped off part of the roof in 2017—but Ian gutted it, flooding the restaurant with more than 4 feet of water. Renovations were already underway to transform the sunbaked patio, with a new thatched hut. The hurricane raised the stakes, turning an aesthetic update into a rescue mission for old Naples history. Over two months, Dan and Doug restored the restaurant, careful to maintain its character. “They’ve done things we couldn’t even dream of,” Tom says of the renewed space that debuted in late 2022. “It feels like the same place.”
Photography by Brian Tietz
Photography by Brian Tietz
Photography by Brian Tietz
Photography by Brian Tietz
That sentiment echoes among locals and visitors. Naples is exploding with new restaurants and luxury developments. As the city changes, The Dock takes on new importance. It stands not just as a restaurant, but as an embodiment of the community’s enduring soul. With its weathered wood, it’s one of the few places where traces of old Naples still feel tangible. “It brings up all these memories,” says Peter Tierney, the restaurateur behind toes-in-the-sand The Turtle Club and The Syren Oyster & Cocktail Bar. He understands the pressure of owning a choice waterfront slice of the city’s tight real estate market. “They could have done anything with that property, and they chose to do the right thing,” he says.
Vin, a defining figure in Naples hospitality and the driving force behind The Dock’s first four decades, passed away in March, shortly after the restaurant’s 50th anniversary. His imprint still lingers inside the restaurant in the photos on the wall and the stories passed down by regulars who now bring their children and grandchildren to The Dock year after year. “The Dock has always been about community,” Dan says. “We’ve always looked at [our role] as being the caretakers for the next 50 years.”