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.
Irish Kevin’s
Live Music
This is the place for great friends and ice cold Guinness! From intimate business deals and family celebrations, Irish Kevin’s is a rustic second home to all its guests. With a high standard of hospitality and knowledgeable servers, it’s easy to kick-back, relax, and enjoy the delicious authentic Irish cuisine and the incredible set of live entertainment each night.
Sloppy Joes
Craft Beer • Live Music
As one of Key West’s most iconic locations and the favorite watering hole of Ernest Hemingway, Sloppy Joe’s boasts visitors from all over the world who come to enjoy their favorite beverage, true Key West atmosphere, and high quality cuisine. There’s always a party in the main bar and Joe’s Tap Room sports a large variety of crafted and specialty beers. Live musical entertainment begins at 12 in the afternoon and rocks until 2:00 a.m.!
Two Friends Patio Restaurant
Breakfast • Live Music
For over 40 years, this family-owned historic landmark has been serving the finest local seafood for lunch and dinner, while offering a sumptuous breakfast beginning at 8 a.m. From conch fritters to the best island steaks and ribs, Two Friends Patio offers true Key West flavor. Conveniently between the famous Mallory Square and Front Street. it features premiere outdoor dining experiences, the best Happy Hour and Karaoke shows.
General Horseplay
Cocktail Bars • Craft Beer
General Horseplay offers live entertainment and tomfoolery, along with craft cocktails and beer in an old brick house.
Hogfish Bar and Grill
American Restaurants • Caribbean
A true locals’ spot overlooking Safe Harbor on Stock Island, is the Hogfish Bar and Grill. Don’t leave without tasting their signature Killer Hogfish Sandwich or Fried Hogfish Benedict. Or how about a Po' Boy or Lobster BLT? Burgers, Tacos, Fish & Chips and decadent soups and chowders. Bring you catch. They will cook that too! Live Music on the weekends make the Hogfish an island gem.
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.
Schooner Wharf Bar
Happy Hour Bars • Live Music
Coined the "Last Little Piece of Old Key West, " it is located in the heart of the Historic Seaport on the water. The Schooner Wharf offers you and your dog a great place to drink, eat and watch the beautiful tall ships come and go. Charles Kuralut called the Schooner Wharf, This must be the center of the universe.” Once you visit, you know why.
Little Room Jazz Club
Jazz Clubs • Live Music
The Little Room Jazz Club is situated on the quieter side of Duval Street. Featuring live music nightly from some of the world’s best blue and jazz musicians around. This cozy club opens at 4pm daily, they serve a large selection of craft beer and wine.
The Bull and Whistle Bar
Happy Hour Bars • Live Music
The Bull and Whistle is two bars in one. Large crowds gather around the central bar to watch the live music on the Bull’s small performance stage, while the Whistle plays host to the sport lovers. Shoot a game of pool, play darts or people watch while sitting on one of the many stools that line its famous balcony. Venture on to the third floor if you are daring. It plays host to Key West’s only clothing-optional bar, aptly named Garden of Eden.
The Green Parrot
Dive Bars • Live Music
The Green Parrot is a true Key West icon and the ideal place to just let loose with your friends and be yourself. Every night, the great music, original beverages, and groups of local regulars combine with Key West visitors to make for a place of misadventures, excitement, and pure fun. From hurricane parties, to divorce celebrations, to pet birthdays, the true Key West spirit of the Green Parrot never changes and welcomes everyone with open arms.
Rick’s Entertainment Complex
Dive Bars • Happy Hour Bars
Rick’s Entertainment Complex has the perfect combination of everything Key West… dance clubs, VIP bars, adult entertainment, premium drink bars, balcony bars sporting incredible views of Duval, and live rock n’ roll entertainment. With eight different bars its a place to taste a little bit of everything, a variety of music venues, and many party zones all under the same roof.
Captain Tony’s Saloon
Dive Bars • Happy Hour Bars
The original Sloppy Joe’s Bar, this historical saloon has been loved for decades by locals and visitors alike, as well as iconic figures like Tennessee Williams, Truman Capote, and, of course, Ernest Hemingway. Capt. Tony was an avid fisherman, rumrunner, casino manager, and even the mayor of Key West, who built the saloon with the intention of offering ice cold drinks to his fellow Key Westers—a tradition that everyone still loves to participate in!
Hog’s Breath Saloon
American Restaurants • Happy Hour Bars
For 25 years, the Hog’s Breath Saloon has served cold drinks, delicious food and live music in their outdoor tropical setting and in the rustic, cool interior of the bar! “Hog’s breath is better than no breath at all!” Enjoy the cool, air -conditioned interior or have a drink outside! Check out their three live webcams or purchase one of their famous t-shirts in the mercantile store!
