Advice from a Conch: six stand-out bars in Key West.
Everybody knows Key West for boozy Duval Street. Jimmy Buffett's song "Last Mango in Paris" memorialized Capt. Tony's Saloon, and Ernest Hemingway spent many nights at Sloppy Joe's. But there's so much more to the bar scene in the Conch Republic, including some great out-of-the-way spots for live music. Jason Mudgett, director of rooms at Southernmost Beach Resort, and local resident for almost a decade, shared his favorite watering holes where you can also enjoy great music.
Hank's Hair of the Dog Saloon
"This spot is a very young and hip place for locals to hang out. They have great music and the best part is they are dog-friendly. I always get a Mermaid Water. It's gin, lemon, and a little bit of lavender — so delicious. And you don't need to dress up. You are fine in shorts and a T-shirt just relaxing, having one of their crafted cocktails or a beer, and hanging out listening to amazing music."
409 Caroline St, Key West, Florida 33040 — (305) 509-7758 — hankskeywest.com
La Te Da
"This is an old bed and breakfast, but inside there's a bar with nightly music," said Mudgett. "They have a group called Threesome, and they are amazing. It's all live singing, and they do everything from the 50s, 60s, 70s, 80s, 90s, and today. The vocal ranges of these singers will blow you away! I usually order a glass of wine here because of the classic setting. The fun thing about La Te Da is they have a dance area and do anything from Luther Vandross to Tina Turner to K.C. and the Sunshine Band. It is such a great little place to go to."
1125 Duval St, Key West, Florida — (305) 296-6706 — lateda.com/cabaret
Virgilio's
"It's a popular spot for locals," said Mudgett. "It's on the back side of La Trattoria in Old Town right on Duval. They have wonderful live music, but something that's a bit special is on Mondays, they do $7 Martini Mondays. I always order the Razzle Dazzle — it has raspberry vodka, Chambord, and sour mix in it. So perfect after a warm Key West day. They also serve a full menu of La Trattoria's food, but most people are there for the intimate ambiance and fabulous martinis."
524 Duval St, Key West, Florida — (305) 296-1075
Southernmost Beach Cafe
"Obviously, I love Southernmost Beach Cafe. We have a delicious Key Lime Colada made with Captain Morgan Spiced Rum, pineapple, coconut, and topped with Keke Key Lime Liqueur…so good," said Mudgett. "It's right on the beach. There's a great atmosphere in a relaxed setting. They have a concert series and live music with great musicians by the pool daily. They do have games on, so if you want to come and watch the game while you're here, you have a dream spot right on the sand, and it's open to the public."
1405 Duval St, Key West, Florida — (305) 295-6550 — southernmostbeachresort.com
General Horseplay
"I like this spot because it's different. It stays very authentic to Key West by bringing its own vibe. Most of the bars here are either sports bars or what we think of as traditional bars. General Horseplay is unique, from the décor and the way the bartenders dress in their funky outfits to the drink choices. They have a Salted Caramel Martini that I absolutely love. It comes with a little sushi cupcake on the side. They also have an indoor and outdoor bar with live music in both areas. I just love the backyard bar. It has a retro 90s diner feel with little diner chairs and booths. Sometimes you can even spot a cat on the roof of the patio listening to the band. It's a great bar to grab a drink and hang out with friends."
423 Caroline St, Key West, Florida — (305) 741-7599 — generalhorseplay.com
Point 5
"This is the only place on my list without live music, but they do have a DJ and draw a young crowd. It's upstairs from the restaurant Nine One Five, which is so good as well," said Mudgett. "Upstairs, they have an indoor bar, outdoor seating, and a DJ area. The atmosphere is colorful — the music, the personality, and everybody's attitude is so upbeat. It's friendly but relaxed and chill at the same time. And they have an insanely incredible Espresso Martini. I probably go there four times a week just to get that Espresso Martini. They also serve the full menu from the restaurant downstairs — it is one of the best places to eat in Key West, hands-down."
915 Duval St #5, Key West, Florida
Story by Carrie Honaker.
Originally published in Beach Happy Magazine, Issue 12 — Spring 2023.
