Key West Bars Near Mallory Square

Sunset Pier

Cocktail BarsOutdoor 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.
Berlin's Martini and Cigar Bar

Cocktail BarsTapas

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.
Key West First Legal Rum Distillery

Distilleries

Tastings, Souvenirs, Tours and more! Rated in USA Today's Ten Best! Come taste history at the Key West First Legal Rum Distillery. Hand made, bottled and labeled proudly in Key West, FL! Come in and enjoy a FREE tasting! Their Legal rum represents the true essence of the 1920’s in Key West... when rum was the drink just like it is today. They have something for the whole family including homemade soda tastings for the kids!
Island Dogs Bar

Craft BeerWine Bars

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!
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 BarsWine 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!
Sunset Tiki Bar

American RestaurantsHappy Hour Bars

Known as where the boardwalk ends and the sunset begins, the Sunset Tiki Bar and Grille is the ultimate hidden gem! Located on the harbor the Sunset Tiki bar is open 7 days a week from 10am-10pm. Savor one of the best views of sunset while listening to live tropical music every evening. Stroll on back to the docks of the Galleon Resort and bask in the great views on the deck or by the pool and enjoy not only one but two happy hours daily.
Little Room Jazz Club

Jazz ClubsLive 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 Chart Room

Dive BarsHappy 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.
Bearded Lady

Craft BeerWine 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.
Flying Monkeys Saloon

Frozen Cocktails

An outside bar, located at the historical Fogarty House, Flying Monkey’s Saloon is a popular spot for locals. One of the only open air bars located right on Duval Street, it is a great place to people watch. Flying Monkeys also offers a variety of frozen drinks for that warm sunny day. Open all day, happy hour nightly.
Mary Ellen's Bar & Restaurant

American RestaurantsCocktail 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.
Willie T's

Happy Hour Bars

Live music fills the air daily at Willie T’s. Popular for its outdoor setting on Duval Street, this bar is well known for it’s famous mojitos. The ceilings and walls are adorned with dollar bills from patrons past. Stop on through, they serve up happy hour daily from 4pm-7pm.
Point5 Lounge at nine one five

Cocktail BarsLounges

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.
Smokin' Tuna Saloon

American RestaurantsSeafood Restaurants

The Smokin’ Tuna Saloon is the best place for good food and music. Offering a raw bar, a generous selection of starters, sandwiches, dinners, sides, and a full bar, this saloon is ideal to sit back, have a drink and listen to a broad variety of live music. As a regular venue for the Key West Songwriters’ Festival, you will never hear a bad tune here. Tucked away on a quiet lane just steps from Duval.
Waterfront Brewery

American RestaurantsBurgers

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!
Wine-O

Wine Bars

A unique and sophisticated wine shop nuzzled in the chaos of Duval Street featuring over 200 bottles from around the world! With an atmosphere of elegance, fine wine and chocolate. Offering a wide assortment of the ever-famous Godiva chocolate, which can be expertly paired with ample wine choices. Enjoy a bottle in our sleek, sophisticated lounge setting, or take it to go, or stay a while and try our by-the-glass list!
Shots and Giggles

Craft BeerWine Bars

Shots and Giggles is a local's favorite bar in Key West, FL. Nestled next to Tattoos & Scars Saloon right off of Greene St., Shots and Giggles is known for its relaxed atmosphere, cold drinks, and always having the game on any of their 5 TVs.
Fat Tuesday

Frozen CocktailsHappy Hour Bars

Straight from Bourbon Street in New Orleans and dropped in the middle of Duval Street comes Fat Tuesday Key West. WARNING: Don’t be a victim of a brain freeze while slurping on one of its famous frozen daiquiris on a hot summer day. Have your own private party as you dance to their house DJ nightly. Fat Tuesday offers happy hour Monday–Friday from 4-7pm. Open everyday from 10am.
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.
Heroes Bar & Liberty Lounge

Craft BeerWine Bars

Heroes Bar & Liberty Lounge is a pub and craft cocktail lounge in the heart of the historic district of Old Town in Key West, FL. All veterans, active duty military members and first responders receive a 20% heroes discount!
Don's Place

Happy Hour Bars

Don’s Place, a ‘locals’ bar for tourists. Located at the corner of Truman and Grinnell Streets, it is an inside air-conditioned bar with an outside tiki bar. Play a game of pool or darts inside or challenge someone in a game of corn hole, ping pong or foosball at the outside tiki-bar while watching your favorite game on the tube. Need to take some liquor home? Its drive up window makes it very convenient. Don’s is the first and last bar you hit off of Duval Street.
Salty Oyster

American RestaurantsCocktail 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.
Aqua Nightclub

Happy Hour BarsLounges

Reality is a drag! Are you looking for the best music, lights, sounds and DJ’s in town? Aqua Nightclub is the premier gay nightspot in Key West. Its friendly staff welcomes all patrons– as well as gays, lesbians, young and old. The club is home to the Aquanettes, who perform drag shows nightly. Happy hour is daily from 3pm to 8pm. Must be over 21 to enter.
Old Town Tavern & Beer Garden

Craft BeerWine Bars

The lively bar where you can mingle with the locals. Air conditioned, smoke free, indoor high tables or cozy benches? Outdoors in the Beer Garden against the rail to watch the comings and goings of Duval Street or at a garden table? They are also pet friendly!