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A Pirate’s Guide To Fire Island

Nine restaurant-pubs in 24 hours

Alas, ’tis come to me attention a great many land dwellers here on the mainland aren’t aware of a special adventure lying just beyond the Great South Bay, an exotic voyage too epic to imagine, a secret too good to keep. Oh, dear landlubbers, ye are surely, surely missing out.

For beyond the waves—a mere 20- to 30-minute ferry ride from Bay Shore, Patchogue or Sayville, fellow scallywags—awaits a treasure trove of magical wonders: Fire Island. Say it loud.


The 32-mile isle stretches through vast wilderness and nearly two dozen seaside communities. All but about four miles is federally protected National Seashore—featuring some of the most gorgeous, pristine beaches in the world. This oceanic paradise is home to about 500 inhabitants year-round, yet hundreds of thousands flock here during the summer months.

’Tis a magical land, dear pillage-marauders. ’Tis a magical land, indeed—full of secrets and legends—and restaurants, taverns and bars galore. Cars aren’t allowed.

During the day Fire Island is a family- and couples-friendly oasis. During the evening, it transforms into an amusement park. Known among locals as the “anti-Hamptons,” Fire Island is surely the Las Vegas of Long Island, minus the gambling.

The heavenly Any Fresher You Would Be Wet Tuna at Surf’s Out in Kismet.

Me cousin Rocky met me at the pier at Ocean Beach, one of the roughly dozen ports accessible from what FI natives dub “The Mainland” (aka the rest of the world). We wasted no time.

First stop: Matthew’s Seafood House, known for its extremely fresh fish. The restaurant offers dockside dining outside, with plenty of tables and a mammoth bar alongside a dance floor inside. Matthew’s menu is loaded—featuring everything from BBQ Baby Back Ribs and Chicken Parmesan to N.Y. Strip Steak, Fisherman’s Stew, Alaskan King Crab Legs and crabmeat-stuffed Maine Lobsters. It’s been family run and operated since 1974.

I was quickly smitten by its friendly staff, arsenal of music, eclectic menu and stocked bar. Every watering hole dotting Fire Island features a specialty drink—Matthew’s is 64 oz.-frozen fishbowl margaritas.

Though two minutes before the restaurant’s kitchen shutdown, our bartender, Jimmy, convinced the cooks to take one final late-night order, suggesting the gorgeous, bountiful Starters Hot Combination ($19): a heaping platter of fresh seafood brimming with juicy, steaming Baked Clams, Fried Calamari, Crab Cakes and Shrimp Scampi. Yes, oh yes, we had struck gold—and rum.

In preparation of a land assault, we squeezed lemons onto the girth, squelching the thirst of the fried squid’s outer, crusty shell and softening its meaty sinews with the sweet lifeblood. One by one we forked through the weighty mass, reverting to bare hands periodically—wrestling those mighty tentacles into the submission that is the 20,000 leagues of my gut.

Utilizing the mollusks as bivalve shovels, we hoisted ’em up and scooped ’em out with our powerful tongues, then swallowing them thar Baked Clams’ precious cargo, one by one. They went down smooth, welcoming. Their thick breaded top made for a rich, fluid chew, hearty yet mushy.

Those Crab Cakes were truly gifts from the depths, dear exoskeletal-crustacean hounds. Their toasted exterior effortlessly gave way to a soft, moist, warm interior. Forking, sending them on one-way voyages to the inner sanctum of me digestive system, I grabbed another them thar slippery arthropods—thick and moist and fleshy, saturated in a lemon-butter sauce that proved key for the remnants of the crabblers. So good.

Another sip of me rum, another lick of me tongue, another chomp of me chompers, another swallow on down.
“Thar she blows!” bellowed me stomach. “Sailor’s delight!”

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