First Flight Island Restaurant & Brewery is a new american restaurant in Old Town, Key West.
Editorially verified August 21, 2026 by Lewis Vaughan, TableJourney editor. Source.
Signature dishes: Fresh local fish, House-brewed beer
Must 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.
Address: 301 Whitehead Street, Key West, FL 33040
Frita's Cuban Burger Cafe keeps a Key West lunch under $15 with Havana-style fritas, tacos and yuca fries on a bright patio just off Southard Street.
Signature: Traditional frita, Yuca fries
Order: The traditional frita with its crown of fried potato strings
Tip: Owner Marcia Weaver built the recipe on trips to Cuba; the churros and Cuban coffee finish the meal properly.
5 Brothers Grocery has pressed Cuban mixes and poured con leche at Southard and Grinnell in Key West since 1978, a family corner store with a bench crew.
Signature: Cuban mix, Bollos
Order: Cuban mix pressed hot, plus a bag of bollos
Tip: The Bench Crew of regulars holds court outside each morning; come before the 06:30 rush clears the pastry case.
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.
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.
Garbo's Grill cooks Korean BBQ tacos from an Airstream in the Hank's saloon courtyard in Key West, twice featured on Diners Drive-Ins and Dives.
Signature: Korean BBQ tacos, Cayo fish tacos
Order: Korean BBQ tacos with a side of island fries
Tip: Order at the truck window and grab a beer from Hank's bar behind you; the picnic tables share the same yard.
Frita's Cuban Burger Cafe keeps a Key West lunch under $15 with Havana-style fritas, tacos and yuca fries on a bright patio just off Southard Street.
Signature: Traditional frita, Yuca fries
Order: The traditional frita with its crown of fried potato strings
Tip: Owner Marcia Weaver built the recipe on trips to Cuba; the churros and Cuban coffee finish the meal properly.
Sandy's Cafe is the laundromat lunch counter of Key West, pressing Cuban mixes and pouring con leche at a White Street walk-up window from 05:00 daily.
Signature: Cuban mix, Cafe con leche
Order: Cuban mix with a large cafe con leche
Tip: Order at the window, eat on the stools facing the street; the buchi shot is the fastest caffeine on the island.
5 Brothers Grocery has pressed Cuban mixes and poured con leche at Southard and Grinnell in Key West since 1978, a family corner store with a bench crew.
Signature: Cuban mix, Bollos
Order: Cuban mix pressed hot, plus a bag of bollos
Tip: The Bench Crew of regulars holds court outside each morning; come before the 06:30 rush clears the pastry case.
