Let me tell you something about getting to Flynn’s. You can’t just show up. There’s no pulling into a parking lot, grabbing a spot, and shuffling in on foot. No, to get to Flynn’s you either captain your own boat (Frank!) into their 50-slip marina, or you buy a ferry ticket and let someone else do the work. Either way, the journey is part of the deal — and honestly, it sets the tone for everything that follows.
Fire Island itself has no cars. No roads, really. Just side streets, some beach cruisers, and a whole lot of people who have figured out that life runs a little better at three miles an hour. Flynn’s fits right into that philosophy.
The Full Story
Flynn’s has been at this since 1937, which in beach bar years is basically the Jurassic period. John “Pop” Flynn and his wife Katherine started the whole thing with a handful of cash and a building they called the Casino. Three generations of Flynns later, the place is still family-run, still on the water, and still pulling people off boats and ferries every summer weekend like it’s got some kind of gravitational pull. If you’re fortunate like we were, you might run into Luke Flynn, who was running the floor the night the Bum visited and made us feel like part of the family. It tells you all you need to know: 86 years in and the person managing your night still has the last name on the sign.
The setup is sprawling. There’s an indoor dining room with exposed wood ceilings, nautical odds and ends, and a hand-painted mural of Fire Island’s coastline running the length of the wall — the kind of detail that tells you this place takes itself seriously in the right ways. Then you step outside, and that’s where Flynn’s really earns its stripes. A wide open deck faces Great South Bay, with the requisite white plastic tables and chairs packed in tight, string lights overhead, and boats bobbing in the slips just below the railing. The sunset views across the bay are flat-out ridiculous. Northwest-facing, wide open, nothing in the way. Come on a clear evening and you’ll be staring at an orange sky that makes you want to order another round just to have an excuse to keep watching.
The bar situation has a few chapters. There’s the main indoor bar — warm wood, proper barstools, a surf rescue boat hanging from the ceiling above the dance floor (the “37” on its hull is not subtle). Then there’s the outdoor bar right on the deck, which is prime real estate if you want to see and be seen. Order the Rocket Fuel: part rum, part Piña Colada, all bad decisions. It shouldn’t work. It absolutely does. Entire nights — and a fair amount of self-respect — have disappeared into that drink.
The food is a full menu — seafood, burgers, flatbreads, a proper ahi tuna poke bowl, and other items that looked amazing. The food’s better than a boat-only bar has any right to be. Just be sure to save plenty of room for that extra Rocket Fuel (that you absolutely do not need).
Insider Tips
Flynn’s is cash-only at the bar. This is Fire Island’s official policy on the modern era, apparently, so stop at the ATM before you get on the ferry. Also: happy hour runs Monday through Friday, 5–8pm, with $7 drinks and discounted eats. It is, in the Bum’s professional opinion, the single best reason to take an afternoon off work.
Beach Bar Bum’s Prime Seat
Grab one of the outdoor deck tables along the water-facing rail, as far west as you can get. You’ll have boats on one side, bay on the other, and enough room to spread out without being directly on top of the speakers. If the deck tables are full, either of the outdoor bars are a perfectly acceptable Plan B.
