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 to 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?
While many parts of Key West have seen modern changes, Schooner Wharf maintains that "old Key West" atmosphere--from the salvaged wreckage to the interesting characters that linger around the waterfront. First-timers to the restaurant should dive right in and try the fresh mahi-mahi or snapper melt with a house mango sauce topped with sauteed onions and mushrooms. Settle into the open-air bar and listen to the daily live music, while you people watch. Animal lovers can bring their dogs--or their parrots--to hang out. Specialty drinks such as Schooner Lemonade, Rumrunners and Mango Daiquiris are featured during the bar's three happy hours. Keep an eye on their calendar of events! Schooner Wharf has theme-night events throughout the year.
The historic seaport offers the quintessential Key West experience: boats bobbing at the docks, fishing and diving boats heading in for the day, and schooners setting out to catch the sun slowly slipping across the sky. The upscale Commodore restaurant has a menu that features both fresh seafood and select cuts of beef. Start off with the crab and avocado cocktail before moving on to the pan-seared grouper with lobster cream sauce. The surf-and-turf is a classic, and the prime rib is a favorite with the regulars. Their Belgium chocolate mousse swirled with raspberry is the perfect ending for any meal. The extensive wine list makes it easy to pair a glass with your entree or opt for one of their specialty martinis.
For a taste of a true local's joint just five minutes away from Old Town, follow the signs to the Hogfish Bar and Grill, located in Safe Harbor Marina on Stock Island. Try anything that's made with their namesake specialty like the "Killer" Hogfish Sandwich, which is smothered in Swiss cheese, onions and mushrooms on a fresh Cuban roll. The Hogfish Fingers or Fried Hogfish Tacos are also favorites or dig into a plate of "Peel 'n' Eat" Key West pink shrimp. All dishes call for an ice cold beer. This open-air, casual restaurant is a diamond-in-the-rough with live entertainment and a popular happy hour. The owners try to maintain that Old Key West vibe, and views of Key West's last working waterfront are a bonus.
Waterfront dining in Key West often comes with a steep price. Not so at the Southernmost Beach Cafe. Here you'll find reasonable deals on casual local fare for breakfast and lunch. You don't have to be staying at the Southernmost Hotel to enjoy the views of the Atlantic. You can stroll in from the sand and have a seat in this open-air restaurant that offers a wide selection of breakfast items, sandwiches, salads and starters. Start your morning with Key West Benedict--poached eggs atop an English muffin and asparagus spears, topped with locally caught Key West pink shrimp and hollandaise. At lunch, opt for tacos packed with the fish of the day or a Reuben Cuban sandwich stuffed with pulled pork, corned beef, Swiss, pickle and mustard. Dinner is a bit more formal (average the entree price is $25) with dishes like the macadamia crusted local grouper with mango salsa. Finish with their homemade Key lime pie with a crisp Oreo cookie crust.
As the sister restaurant of famed Blue Heaven, Salute! On the Beach applies the same high standards to Caribbean-Italian fare. This charming cafe on Higgs Beach, between White Street Pier and Casa Marina, has a laid-back atmosphere with ocean views. Stop by in flip flops and tees for a light lunch, featuring gazpacho, Caprese salad and fresh yellowtail sandwiches. Or make reservations for dinner where the menu is filled with appetizers like sautéed sea scallops with ciabatta crostini and entrees like Salute house-made pasta with Mussels, white wine and butter. They also have several vegetarian options. Mojitos and other tropical cocktails are well-prepared and invite guests to linger. Don't pass up the homemade chocolate chip ice cream sandwiches. As a plus for pet-lovers, they can bring Fido along (although he isn't allowed on the beach itself).
With island roots that date back to 1947, A&B Lobster House is an institution in Key West. This upscale restaurant features rich classics like Lobster Bisque laced with cognac, Lobster Thermidor or Sunset Surf and Turf with filet mignon. For something on the lighter sight, their savory Bouillabaisse simmers with jumbo shrimp, clams, mussels and the local catch in a saffron fennel broth. With fantastic views of the Key West Bight, their wrap-around balcony is perfect for that romantic evening. Head to Berlin's, their cigar and cocktail bar, for your nightcap of fine cognacs, dessert wines and specialty martinis. Their elegant white tablecloth dining experience does come with a rather hefty price tag (entrée prices range from $25 to $68), but that makes A&B perfect for that special occasion.
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 lobster stuffed crab cake, savory lobster bisque and pickled Key West Pink Shrimp to your table--and those are just the appetizers. Latitudes round 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.
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.
An upscale Caribbean-American restaurant, Louie's Backyard offers island specialties like conch fritters spiced up with 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.