Table of Contents
Blue Heaven
Breakfast beneath banana trees and free-roaming roosters — this legendary Bahama Village spot is pure Key West chaos. The banana bread French toast is outrageous, and the lobster Benedict is worth every penny. Get there early; the wait is part of the ritual.
Louie's Backyard
Fine dining on a wooden deck literally hanging over the Atlantic. The seafood is pristine, the cocktails are potent, and watching the sunset from the back bar is a borderline religious experience. Dress up (by Key West standards) and splurge.
Half Shell Raw Bar
An old waterfront fish shack at the Historic Seaport where oysters are shucked fresh and served cheap. The conch fritters are golden and crispy, and the harbor views come free. No pretense, just excellent seafood and cold beer.
Eaton Street Seafood Market
A locals-only counter with the freshest fish in town and zero attitude. Order whatever came in that morning, grilled with a squeeze of lime. The lobster roll is superb, and eating at the plastic tables outside is part of the charm.
DJ's Clam Shack
Cash-only roadside stand serving golden fried clams and lobster rolls that punch way above their weight class. The chowder is thick and briny, and the whole operation is gloriously unpretentious. Don't overthink it, just order.
Conch Republic Seafood
Massive waterfront spot with live music, sunset views, and a solid raw bar. The stone crab claws are cracked fresh, and the conch ceviche is zippy and fresh. It's touristy but actually delivers on the food.
The Stoned Crab
A casual spot on the way to the island serving fresh-cracked stone crabs at fair prices. The mustard sauce is tangy and perfect, and the vibe is no-frills Keys all the way. Stop on the drive down and feast.
Green Parrot Bar
Key West's oldest bar, and still one of its rowdiest. The parachute on the ceiling, the pool table, the live local bands — it's all gloriously sticky-floored and real. Skip the Duval Street nonsense and come here instead.
Sunset Pier
The best seat in town for the nightly sunset celebration, with cocktails and the Gulf spread out before you. Claim a spot at the bar, order a frozen drink, and applaud when the sun dips. Pure, cheesy, Key West magic.
Sunset Tiki Bar
A chill dockside tiki bar where you can watch the boats come in and the sun go down. The drinks are strong and fruity, and the pace is slower than slow. Perfect for that third or fourth drink of the evening.
General Horseplay
A newer addition to the Key West drinking scene with craft cocktails and a vintage lounge vibe. The bartenders know their classics, and there's room for grown-up conversation. A welcome escape from the Duval Street madness.
Willie T's
A Duval Street staple with loud music, cold beer, and serious late-night energy. The upstairs balcony is perfect for people-watching, and the party goes until the small hours. It's messy, it's loud, it's Key West.
Sloppy Joe's
Hemingway's old haunt, now a tourist institution but still worth a stop. Get a beer, take a photo, and pay your respects to the Papa mythology. The live music is solid, and the history is real.
Rick's Bar
A multi-floor Duval complex with a rooftop, a dance floor, and peak bachelorette-party energy. It's chaotic and sweaty and exactly what it promises. Sometimes you just need to lean into the madness.
The Bull
Another Duval Street landmark with multiple bars, a clothing-optional garden bar, and legendary late nights. The rooftop at Garden of Eden is... an experience. Embrace the chaos.
Two Friends Patio Restaurant
An unpretentious Duval spot with solid breakfast and a killer Bloody Mary bar. The karaoke is legendary, and the food is surprisingly good for the location. A local favorite hiding in plain sight.
Harpoon Harry's
Early-morning diner vibes with fishermen and locals crowding the counter for eggs and coffee. It's old-school Key West, with formica tables and no-nonsense service. The perfect hangover cure.
Square Grouper Key West
Cudjoe Key gem with fresh fish and a laid-back vibe that feels like old Florida. The catch of the day is always stellar, and the waterfront deck is pure bliss. Worth the drive for a long lunch.
