Dining Out and Nightlife
Intimate restaurants with island decor feature traditional Key West cuisine — fresh-caught fish, roast pork with yellow rice and black beans, lobster, snapper, stone crabs, grouper — all topped off with a big slice of Key lime pie. And don't forget to try a Cuban sandwich for lunch, and get “conched out” on conch, whether in chowder, salad, or fritters.
Abbondanza Italian Restaurant: Generous portions of reasonably priced Italian cuisine, served in a bright family atmosphere. (1208 Simonton Street, 305-292-1199)
Conch Republic Seafood Company: Dine alfresco on succulent seafood, prepared Caribbean style, in a former sponge-inspection warehouse on the wharf, overlooking the Key West Historic Seaport. (631 Greene Street, www.conchrepublicseafood.com)
Kelly's Caribbean Bar, Grill and Brewery: This micro-brewery, housed in the former offices of Pan American Airways, serves up a varied menu, accompanied by its own beers. (301 Whitehead Street, 305-293-8484)
Lobo's Mixed Grill: One of the best lunch eateries in Key West and one of the best family values, serving conch chili and thirty different types of wraps, each a unique culinary creation. (5 Key Lime Square, 305-296-5303)
Mangoes Restaurant: This restaurant serves a blend of Caribbean and Mediterranean food, plus brick-oven pizzas, in five different dining areas — in dining rooms upstairs and down, on a balcony overlooking the action on Duval Street, in a tropical garden, and on an outdoor patio. (700 Duval Street, 305-292-4606)
Pepe's Café: The town's oldest restaurant and its funkiest, dating from 1909, serving three meals a day, including gourmet coffees, great burgers, pork chops, and steaks. (806 Caroline Street, 305-294-7192)
Unlike the rest of the Keys, Key West hops at night due to its rather bohemian atmosphere. The festivities begin with the nightly sunset celebration at Mallory Square. Though it began as a spontaneous celebration and an excuse to drink beer and smoke pot in public back in hippie days, today it's a choreographed tourist affair, but fun, nonetheless. Singers, dancers, jugglers, and magicians in colorful costumes are all part of the scene.
JUST FOR PARENTS
Step onto the 43-foot yacht Dreamchaser for a gourmet dinner for two to six of lobster tail or steak prepared by your own private chef. You'll receive a welcome rum punch or cold beer and conch fritter and shrimp appetizers, and strawberry shortcake for dessert, for $82 per person as you sail into the sunset. (305-292-8667)
Sample some culture by attending a play, concert, or dance performance at the Tennessee Williams Fine Arts Center from November to May. You can also tour this modern Bauhaus-inspired theater during the off season (305-296-1520, www.tennesseewilliamstheatre.com). There's also the Waterfront Playhouse (305-294-5015) and the Red Barn Theater, which stages new plays by local playwrights (305-296-9911).
Bars of every description make up the bulk of Key West nightlife. Most stand along the upper end of Duval Street and offer a gregarious mix of locals and tourists dancing to live rock or country music. One of the most popular among tourists is Sloppy Joe's on Duval Street, normally packed to the walls. Hemingway drank here in the 1930s. And, of course, there's the Margaritaville Café, owned by Florida singer and songwriter Jimmy Buffet.

