New American$$$duval-streetDaily 17:00-23:00
Nine One Five serves an eclectic fusion menu from the porch of an 1850s Victorian on upper Duval in Key West, backed by a deep wine list and late seatings.
Signature: Bacon-wrapped dates, Cedar plank salmon
Order: Bacon-wrapped dates from the porch menu
Tip: Ask for a veranda table at sunset; the upstairs Point Five bar pours the same wine list without the wait downstairs.
French$$$white-streetDaily 17:00-21:00
Cafe Sole has cooked French-Caribbean dinners in a Key West backstreet since 1995, John and Judy Correa's kitchen of hogfish and portobello mushroom soup.
Signature: Hogfish, Portobello mushroom soup
Order: Hogfish from the local catch, then the duck a l'orange
Tip: The Correas close for the whole of September each year and reopen in October, so plan shoulder-season visits around it.
Cuban$$old-townMon-Thu 11:00-21:00; Fri-Sun 11:00-22:00
El Meson de Pepe plates ropa vieja and lechon asado beside Mallory Square in Key West, run by the Diaz family with salsa bands playing at sunset.
Signature: Ropa vieja, Lechon asado
Order: Ropa vieja with black beans and plantains
Tip: Time dinner around the Sunset Celebration next door; the patio band starts as the crowds gather on Mallory Square.
Seafood$$historic-seaportDaily 11:30-21:30
Conch Republic Seafood Company fills the old Singleton fish house on Key West's seaport with peel-and-eat pink shrimp, conch chowder and a long raw bar.
Signature: Key West pink shrimp, Conch chowder
Order: Peel-and-eat Key West pink shrimp
Tip: The original Singleton ice-plant floor and sign are still in place; sit at the harbour rail for the shrimp-dock view.
Seafood$$historic-seaportDaily 11:00-22:00
Half Shell Raw Bar shucks oysters and cures conch ceviche in a licence-plate-lined shed on Key West's Margaret Street docks, open to the harbour breeze.
Signature: Conch ceviche, Broiled garlic oysters
Order: Conch ceviche and a dozen on the half shell
Tip: Happy hour brings discounted oysters; the open-air room on the water is first-come, so aim for off-peak afternoons.
Seafood$$stock-islandDaily 11:00-22:00
Hogfish Bar & Grill sits on Stock Island's Safe Harbor docks outside Key West, frying its namesake fish onto Cuban bread beside the working shrimp fleet.
Signature: Killer Hogfish sandwich, Grouper reuben
Order: The hogfish sandwich with Swiss and mushrooms on Cuban bread
Tip: It is a 10-minute drive from Old Town on the Stock Island marina; go at lunch to watch the boats unload the catch.