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.
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.
Island Dogs Bar
Burgers • Craft Beer
Island Dog welcomes both locals and tourist for a laid back experience, with affordable drink and delicious food. Come and enjoy live music every weekend!
Island Dog welcomes both locals and tourist for a laid back experience, with affordable drink and delicious food. Come and enjoy live music every weekend!
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.
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.
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.
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 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 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.
Little Room Jazz Club
Cocktail Bars • Live Music
Little Room Jazz Club is an intimate jazz venue offering live performances multiple nights each week. Known for its cozy atmosphere, craft cocktails and small plates inspired by American soul food, this club is a go-to spot for jazz lovers and anyone seeking a relaxed, music-filled night in Key West.
Little Room Jazz Club is an intimate jazz venue offering live performances multiple nights each week. Known for its cozy atmosphere, craft cocktails and small plates inspired by American soul food, this club is a go-to spot for jazz lovers and anyone seeking a relaxed, music-filled night in Key West.
Waterfront Brewery
American Restaurants • Burgers
Opened in 2015, the Waterfront Brewery is a working brewery, restaurant, and entertainment center located in the heart of old town overlooking the Key West Historic Seaport and Bight. They’re constantly coming up with new brews, many of which have won awards! The food is as lovingly handcrafted as their beers! Bring your friends for some games, fun, and relaxation while admiring the spectacular view. They aren’t called “Waterfront” for nothing!
Opened in 2015, the Waterfront Brewery is a working brewery, restaurant, and entertainment center located in the heart of old town overlooking the Key West Historic Seaport and Bight. They’re constantly coming up with new brews, many of which have won awards! The food is as lovingly handcrafted as their beers! Bring your friends for some games, fun, and relaxation while admiring the spectacular view. They aren’t called “Waterfront” for nothing!
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.
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.
Hurricane Hole
American Restaurants • Burgers
From the dockside bar and grill, complete marina, wide range of watersports options and upstairs restaurant overlooking the harbor, Hurricane Hole Marina is a treasure waiting to be discovered from sunup to sundown. Known as "The Hole" by locals the complex is a one-stop dining and recreational shop for those wishing to experience the best the Keys has to offer. So, plan to relax, stay awhile, and have fun.
From the dockside bar and grill, complete marina, wide range of watersports options and upstairs restaurant overlooking the harbor, Hurricane Hole Marina is a treasure waiting to be discovered from sunup to sundown. Known as "The Hole" by locals the complex is a one-stop dining and recreational shop for those wishing to experience the best the Keys has to offer. So, plan to relax, stay awhile, and have fun.
General Horseplay
Cocktail Bars • Craft Beer
General Horseplay offers live entertainment and tomfoolery, along with craft cocktails and beer in an old brick house.
General Horseplay offers live entertainment and tomfoolery, along with craft cocktails and beer in an old brick house.
Bearded Lady
Craft Beer • Wine Bars
The Bearded Lady offers a selection of 40 different beers, both domestic and import. They even have local brews on tap! Enjoy good beer right off of Duval Street.
The Bearded Lady offers a selection of 40 different beers, both domestic and import. They even have local brews on tap! Enjoy good beer right off of Duval Street.
The Chart Room
Dive Bars • Happy Hour Bars
If you are looking for a no fluff, no frills bar…this is the place! Off the beaten path, this watering hole embraces the history of Key West and its characters. For nearly 40 years, this small dive bar has been on the grounds of the Pier House Resort. Famous faces like Jimmy Buffett and Capt. Tony have gathered here to laugh, lie and take aim at others. Free popcorn, peanuts and hot dogs await any visitor.
If you are looking for a no fluff, no frills bar…this is the place! Off the beaten path, this watering hole embraces the history of Key West and its characters. For nearly 40 years, this small dive bar has been on the grounds of the Pier House Resort. Famous faces like Jimmy Buffett and Capt. Tony have gathered here to laugh, lie and take aim at others. Free popcorn, peanuts and hot dogs await any visitor.
