Rams Head Southernmost
Burgers • Caribbean
Rams Head was founded in Annapolis, Maryland and has been family owned and operated since 1989. With roots in Key West, Rams Head is proud to be part of the local community and is committed to providing the best in Food, Fun, and Beer.
Tin Cup Chalice Bar & Chill
American Restaurants • Caribbean
Whether you’re in the mood for a classic rum runner or our signature frozen concoction, it’s always 5 o’clock at Tin Cup Chalice Bar & Chill. This poolside paradise serves up a spectacular array of tasty tropical beverages and bites throughout the day and well into the night. Located on the Margaritaville Beach House grounds.
Tipsy Rooster Liquor Store & Bar
Cocktail Bars
Drink Now….Its cocktail time all the time in Key West! Enjoy specialty cocktails made with house-infused liquors and a pizza while relaxing in the sand. Or you can stop by the liquor store and buy the perfect ingredients to make your own Key West cocktail.
Mary Ellen's Bar & Restaurant
American Restaurants • Cocktail Bars
Mary Ellen's Bar & Restaurant is nestled on Appelrouth Lane, right off of the famous Duval Street. They are known for beer and cocktails, as well as the cheesiest grilled cheese sandwiches and an extensive beer can collection.
22&Co
Cocktail Bars
22&Co in old town Key West features fresh cocktails, fun bartenders, tutus, flamingos, and unicorns. Need we say more?
The Roost
Cocktail Bars • Wine Bars
The Roost is your friendly neighborhood liquor store and bar with classic craft cocktails, fine wine, and small bites located just steps from Duval Street in Old Town Key West. They offer something for everyone such as delicious small plates of smoked salmon, caviar service, and more… along with an extensive liquor store!
General Horseplay
Cocktail Bars • Craft Beer
General Horseplay offers live entertainment and tomfoolery, along with craft cocktails and beer in an old brick house.
Four Marlins
Breakfast • Brunch
Enjoy a culinary adventure with regional flair at Four Marlins. Savor ocean to table highlighting the freshest, locally sourced seafood and produce. Enjoy an extensive selection of the finest rums, specialty cocktails, ice-cold draft beer, and a thoughtfully selected wine list.
Salty Oyster
American Restaurants • Cocktail Bars
From Key West pinks by the dock to a Mango Overboard in your private cabana, Salty Oyster Dockside Bar & Grill offers fresh fare and tasty drinks in a comfortable atmosphere, just steps from the pool.
Conch Republic Seafood Company
American Restaurants • Burgers
Experience true dock-to-dish dining as you enjoy the incredible views of the Historic Seaport inside our fully open air restaurant! Often, you’ll see our very own fleet of boats unloading their catches of fresh fish, stone crab and Caribbean Lobster!
Dante's Pool Bar & Restaurant
Cocktail Bars • Happy Hour Bars
Dante's an Aquaholics Paradise! A crystal clear swimming pool warmed by its cascading waterfall, friendly servers bringing you ice cold tropical libations and tasty treats as you sun, swim, dance and party. Try our mouth-watering delights, Stone crabs, lobster, oysters and always the freshest local fish, transformed into tacos, po’ boys and platters. Join us for sporting events on 17 TV’s, sunset dinners and the keys most dangerous Happy Hour! It's all about the people, both local and visitor, and their love of two things; the water and a good party!
Sunset Pier
Cocktail Bars • Outdoor Seating
Adjacent to Mallory Square along the boardwalk you will find the Sunset Pier. Enjoy breathtaking views of the world famous sunset while indulging in Caribbean delights from their tiki-bar. Nightly music and dancing surround you as you perch atop one of their waterfront bar stools. Sip on a tropical beverage as your watch the sunset into the horizon making it the perfect ending to a marvelous day.
Louie's Upper Deck
American Restaurants • Caribbean Restaurants
Magical panoramic views of the Atlantic Ocean await you at the Upper Deck at Louie’s. Fine wines by the glass or bottle are served as a perfect compliment to the small plates of focaccia, carpaccio, oven-fresh gourmet pizzas and more. Open 5-10pm, Tuesday through Saturday. A local and visitor favorite for over 25 years.
The Rum Bar
Cocktail Bars
Situated in the home of the late Raul Vaquez, a cigar selector and rum-runner of the early 1920’s, the Rum Bar has the largest selection of rums on the island. Spectacular cocktails, not just rum, await you as you sit quietly on the porch watching the passerby’s on Duval Street. Located on the first floor of the Speakeasy Inn, this laid back spot is a must see on your visit.
Berlin's Martini and Cigar Bar
Cocktail Bars • Tapas
A perfect conclusion to any evening would be a visit to Berln’s Martini and Cigar Bar. Relax in their oversize classic furnishings while peering out into the Key West Harbor. Their signature martinis and dessert wine complement an array of cigars. Choose from their selection of rare smokes or bring your own to sample. There is no other place on the island like this.
Point5 Lounge at nine one five
Cocktail Bars • Lounges
The upstairs from nine one five, POINT5, offers delectable hors d’oeuvres, original cocktails, and a full selection of wine. After dinner, POINT5 becomes an upbeat dance party. There’s plenty of fun to be had under the Victorian columns, filament lights, and awesome food.
Grand Café
American Restaurants • Cocktail Bars
Featuring one of the finest wine lists in Key West, the Grand Cafe is reminiscent of café dining in Europe. Situated in an old Victorian home, the Grand Café offers a full wrap-around porch for those lazier days with a great view of Duval Street perfect to people watch. Guests can enjoy a full selection of wine, martinis, beer and, of course, delectable seafood and fine meats.
