From a basic pasta basilico (linguine with basil, tomatoes, garlic, and olive oil) and filet mignon to fish dishes and grilled bison strip steaks, Rooftop Cafe (308 Front St., 305/294-2042, 9:30 a.m.–10 p.m. daily, main courses from $18) has plenty on its menu to be proud of, but it is the rooftop deck, thick with foliage and boasting great views of the city, that draws the crowds in. Even the indoor seating area, with its wraparound windows and island-style ceiling fans, feels like an outdoor dining room.

There are few places in the thick of Duval Street’s tourist zone willing to claim that “Hemingway never liked this place,” but Bagatelle (115 Duval St., 305/296-6609, 11:30 a.m.–11:30 p.m. daily, main courses from $14) has plenty of history without drawing a tenuous line to the author’s adventures in Key West. The building in which it’s housed dates back to the 1880s, but the menu—with its combination of fresh seafood, tropical produce, French panache, and Southern flair—manages to trace the outlines of Key West’s culinary traditions.

There may be no other place in town that serves up a portobello and avocado egg roll like Bagatelle’s, but even the simple modifications of classic dishes—sweet curry chicken, honey-fried lobster tail—are refreshingly decadent and thoroughly interesting.

The first tickets sold for Pan-American Airways were sold out of the Key West building that currently houses Kelly’s Caribbean Bar Grill & Brewery (301 Whitehead St., 305/293-7897, noon–9:30 p.m. Sun.–Thurs., noon–10 p.m. Fri.–Sat., main courses from $14), and this fact is hard to escape from the minute you step onto the porch. One can almost imagine one of those 1920s seaplane pilots feasting on a bowl of conch chowder or one of Kelly’s eight-ounce pork chops with andouille and cornbread stuffing. Fresh fish is prepared here in several different ways, but one of the best options is to get a filet encrusted with macadamias and banana rum butter.