2 american spots in Historic Seaport, editor-picked by TableJourney. All of Historic Seaport's food · All american in Key West.
Pepe's Cafe ★ 4.4
806 Caroline Street, Key West, FL 33040
Pepe's Cafe has fed Key West since 1909 and calls itself the oldest eating house in the Keys, shucking oysters and baking bread on Caroline Street daily.
Tip: The 2026 Bubba awards gave Pepe's best mojito and best margarita on the island; happy hour runs 16:00 to 18:00.
Harpoon Harry's ★ 4.4
832 Caroline Street, Key West, FL 33040
Harpoon Harry's calls itself Key West's last true diner, flipping key lime French toast and blue plate specials on Caroline Street from 06:30 every day.
Tip: It is cash only with bike racks out front; the nightly blue plate special is the best value dinner near the seaport.