American$$duval-streetMon-Thu 10:00-02:00; Fri-Sat 10:00-04:00; Sun 10:00-02:00
Willie T's papers its Duval Street porch in signed dollar bills and pours mojitos over live music from 11:00 to 01:30, with a full Key West seafood menu.
Signature: Mojitos, Fresh seafood plates
Order: A fresh-mint mojito and whatever fish is on the board
Tip: Add your own signed dollar to the tens of thousands on the walls; the kitchen serves lunch through late night.
Mediterranean$$new-townDaily 07:30-00:00
Kennedy Cafe cooks to midnight in New Town and delivers until 23:30, the late Mediterranean kitchen that feeds Key West's hospitality shift workers.
Signature: Uzbek pita breads, Falafel
Order: Falafel on the house-baked Uzbek pita
Tip: It is a locals' strip-mall room away from Old Town with free parking, and one of the few island kitchens open past 23:00.
Mediterranean$$white-streetDaily 11:00-22:00
Oasis Mediterranean Cuisine hand-folds Turkic manti and khachapuri in a garden room on White Street, Key West's Central Asian outlier worth the detour.
Signature: Manti, Chicken shawarma bowl
Order: Manti dumplings, then the chicken shawarma bowl
Tip: The lush back garden is the seat to take; the somsa pastries and baklava travel well for a beach picnic.
New American$$old-townDaily 11:00-22:00
First Flight serves chef-driven plates and house beer in the 1927 building where Pan Am sold its first tickets, under a Key West garden tree canopy.
Signature: Fresh local fish, House-brewed beer
Order: The local catch with a Main Squeeze citrus wheat ale
Tip: Ask for the Tree-Top deck or the Crash Bar, whose counter is a riveted aluminium airplane wing.
Seafood$$historic-seaportDaily 07:00-21:00
B.O.'s Fish Wagon is Key West's driftwood shack at Caroline and William, frying grouper sandwiches and cracked conch under a roof of netting and plates.
Signature: Grouper sandwich, Conch fritters
Order: Fried grouper sandwich with key lime sauce
Tip: It is open-air and cash-friendly chaos; go at off-hours because the shack smells like fried fish for good reason.
Seafood$$duval-streetDaily 11:00-16:00, 17:00-21:00
DJ's Clam Shack butters warm lobster rolls from a Duval Street counter in Key West, a Diners Drive-Ins and Dives stop with steamed clams and fritters.
Signature: Maine lobster roll, Conch fritters
Order: The warm buttered Maine lobster roll
Tip: Seating is a handful of sidewalk stools, so time it outside the Duval Street lunch rush.