Best Locals Hangout: For a taste of a local hangout that is far removed from Old Town, follow the signs to the Hogfish Bar and Grill, located in Safe Harbor on Stock Island. This open-air, casual restaurant is a diamond-in-the-rough with a lunch menu chock-full of seafood sandwiches (think fish tacos, shrimp Po' Boys, lobster rolls, and their signature "Killer" Hogfish). When dinner rolls around, order the crab cake-stuffed shrimp or the lobster pot pie, and don't forget about the fried green tomatoes! They also serve up a pretty mean breakfast, including items like the hogfish Benedict, shrimp and grits, and warm buttermilk pancakes. It's a perfect alternative if the wait at Blue Heaven is unreasonable, and you can't beat the setting.
Best People Watching: While many parts of Key West have seen modern changes, Schooner Wharf maintains that "old Key West" atmosphere - from the salvage wreckage decor, to the interesting characters that linger around the waterfront. It is also the home of the largest fleet of working schooners on the East Coast, and for two years the bar was actually located on the Schooner Diamante before moving to its current location. The restaurant has seen a number of returning customers, including a couple from Long Island who have been regulars for 17 years. As "Schooner legend" goes, they once found a pearl in an oyster that they were eating and promptly ordered another dozen.
Best Island Escape: Escape to this private island for elegant toes-in-the-sand dining and panoramic Gulf views. After a quick ride on the ferry across the Key West Harbor to Sunset Key, settle in at Latitudes for dinner and a show--the stunning sunset. With sailboats gliding past, you'll feel like a VIP, as well-trained servers bring bring lobster stuffed crab cake, savory lobster bisque and pickled Key West Pink Shrimp to your table--and those are just the appetizers. Latitudes rounds out the seasonal menu with tantalizing selections like pan-roasted rosemary cobia, Wagyu beef skirt steak and seafood pasta. Make sure you save room for dessert. You'll want to relax on this slice of paradise as long as possible. Try the beignets--light puffs of doughy goodness so delicious you may not want to share. Have your camera ready as the sun drops from the heavens--you'll be hard-pressed to find a better perch. Reservations are required, so arrive a few minutes early for the ferry.
Best Toes in the Sand Experience: You don't have to be staying at the Southernmost Hotel to enjoy the ocean view and atmosphere at the Southernmost Beach Cafe. Stroll in from the sand and have a seat in this ultra-casual, open-air restaurant that offers a wide selection of sandwiches, salads, and starters. Try the crispy, tropical chicken salad, the mango pulled pork sandwich, the daily ceviche, or build-your-own burger. Arrive at the restaurant early (just after sunset) and enjoy a breakfast of strawberry, walnut, banana, or chocolate chip hot cakes with Vermont maple syrup, croissant sandwiches, fruit and yogurt, or the freshly-baked quiche of the day.
Best Unkept Secret: An upscale Caribbean-American restaurant, Louie's Backyard has been a go-to spot for al fresco dining since 1971. Their island specialties include conch fritters spiced up with a hot pepper jelly or a unique version of shrimp and grits made with Key West pinks, mushrooms and bacon. Finish with a slice of refreshing Key lime pie with a twist--a gingersnap crust. Upstairs--called the Upperdeck--is a touch more casual with a wine bar and elegant small plates. Sample roasted clams or flaming Ouzo shrimp while enjoying panoramic views of the Atlantic. Their back deck--called the Afterdeck--is perfect for a happy hour cocktail or after-dinner drink by the water before a night on the town. Make reservations well in advance, and time your meal to coincide with the colorful sunset.
Best Chicken Spotting: In Key West, this restaurant needs little introduction. Enter a private courtyard to find roaming chickens, lounging cats soaking in the sun, and live music lingering in the air. Grab a seat outdoors under the shaded canopy or indoors in the "tree house" or dining room. Southern and Caribbean fare is served for breakfast, lunch, and dinner, but breakfast is always jam-packed. Expect jerk chicken sandwiches and shrimp melts for lunch, pork tenderloin and snapper in citrus sauce for dinner, and at breakfast, the lobster Benedict is the way to go. Parking is extremely limited, so to be courteous to the neighbors walking or bike riding is encouraged.
Best History Lesson: From the outside, Pepe's doesn't look like much, and this restaurant doesn't claim to be anything it's not - which may be why it's been open for more than 100 years. The outdoor patio is the equivalent to an old friend's backyard. Breakfast consists of good-old-fashioned Chock Full O' Nuts coffee, homemade sweetbreads, fresh orange juice, chipped beef on toast, and traditional omelets. As the oldest eatery in the Keys (a Cuban fisherman opened it in 1909), Pepe's is worth a visit for the history alone. For lunch, try one of Pepe's grilled burgers, homemade chili, or a fish sandwich. Dinners revolve around steak items and the evening specials. Monday night is meatloaf, Tuesday is seafood night and each Thursday a traditional Thanksgiving dinner is served. Thick cuts pork chops served with buttery mashed potatoes and steaks smothered in sauteed mushrooms are always popular and available.
Best Live Music: Many of Duval Street's pubs are hole-in-the walls devoid of any natural light, but the Tuna is tucked away on Charles Street, leaving plenty of room for a sprawling outdoor area with a large performance stage and several outdoor tiki-style bars. Live music kicks off every night, with two shows on the weekends (check their online schedule). The restaurant and raw bar remains open until 10pm, but the fun continues after the kitchen closes. The menu has all your Key West favorites: conch fritters, peel and eat shrimp, fish sandwiches, burgers, a raw bar, and of course, tuna melts and smoked tuna dip. Grab a seat at the bar or find a spot in the shade under the giant tree, order yourself a bottle of their Smokin' Tuna Ale (or one of their killer margaritas), and enjoy the show.
Best Eating with Your Fingers: Just like the classic waterfront joints of Key West past, the Half Shell Raw Bar serves the freshest seafood in a casual atmosphere. You can actually watch your dinner being unloaded from the boats at the docks, while looking out over the Historic Seaport. The Shrimp Po' Boy sandwich and the conch ceviche are two of their timeless menu options. Grab a picnic table by the water or head for the funky bar, which was featured on the cover of Kenny Chesney's single "When I See This Bar." No white linen dining here, expect paper plates and plastic utensils, but when you're digging into piles of peel n' eat shrimp, oysters, clams and stone crabs, does it really matter?
Best Sunset Views: For upscale dining with a stellar view of the sunset, head to Hot Tin Roof at Ocean Key Resort and Spa located just off Mallory Square. You can dine alfresco on their patio with the sounds of Jimmy Buffett classics wafting up from the band on Sunset Pier, as boats ply the aquamarine waters in the harbor. The Pan-Latin menu offers small and large plates, so you can design your own meal, whether shared tapas-style or traditional entrees. Dishes like the Key lime fish ceviche, paella and caramelized grouper capitalize on the fresh local seafood. Finish with their delicious Key lime pie in a cashew graham cracker crust. You'll love the dusting of cinnamon in the shape of a palm tree on the plate. The understated elegance makes this a perfect spot for romantic couples. Note that the requested attire is resort casual. Average dinner prices range from $10 for small plates to $35 for entrees.