Key West's Iconic Dive Bars & Watering Holes

Key West’s storied past and history are best told and experienced through its legendary dive bars and watering holes. Each with its own story and unique atmosphere, these establishments are not just places to drink; they are institutions that embody the island’s spirit. In addition to great drinks, all of these venues offer live music and something unique that brings the spirit of Key West alive. Here are four must-visit spots that take us on a journey through time and a true taste of Key West: Schooner Wharf Bar: A Last Little Piece of Old Key West, Captain Tony’s Saloon: A Key West Legend, The Green Parrot: A Key West Institution Since 1890, and Sloppy Joe’s: A Key West Tradition.

Schooner Wharf Bar: A Last Little Piece of Old Key West

Location: 202 William St, Key West, FL 33040
Website: Schooner Wharf Bar

Nestled in the historic seaport, Schooner Wharf Bar captures the maritime spirit that has long defined Key West. Celebrated as “A Last Little Piece of Old Key West,” this bar is more than just a drinking spot; it’s a community hub where stories of the sea are shared over cold drinks and fresh catches. Known for attracting colorful characters, both human and animal, Schooner Wharf embodies the laid-back, old-time Key West vibe. Whether it’s the resident parrots greeting guests with their squawks, the local fishermen swapping tales of their latest catch, or visitors from afar sharing their tales. Schooner Wharf Bar is a place where memories are made and friendships are forged in this open-air, laid-back setting. The eclectic mix of people you meet here will keep you coming back time and time again.

Did you know? Schooner Wharf Bar opens as early as 8 AM and offers two happy hours daily: 8 AM – 12 PM and 5 PM – 7 PM, perfect for early risers and sunset seekers alike. The bar is also known for its nightly magic shows, which add a touch of amazement and newfound energy to the atmosphere. Live music is a staple here, providing a lively soundtrack to your day from noon to late at night. The bar features a variety of local musicians and special guest performers, ensuring there’s always great entertainment to enjoy throughout the day and evening.

Captain Tony’s Saloon: A Key West Legend

Location: 428 Greene St, Key West, FL 33040
Website: Captain Tony’s Saloon

Captain Tony’s Saloon is steeped in history and stands as one of the quintessential dive bars in Key West. Located at 428 Greene Street, this iconic venue is filled with fascinating tales and quirky decor that make it a unique experience for all who visit. Constructed in 1851, the building initially served as an ice house and city morgue. Over the years, it functioned as a telegraph station, cigar factory, and even a bordello. It was the original home of Sloppy Joe’s before the bar relocated in 1937. In 1958, Captain Tony Tarracino, a local charter boat captain, purchased the bar and renamed it Captain Tony’s Saloon. If these walls could talk, they would surely have stories to tell! Photo credit: keywestted on Instagram.

Key West's Iconic Dive Bars & Watering Holes 1

Unique Features and History

Decorated with an eclectic array of memorabilia, including bras, business cards, and dollar bills signed by patrons, Captain Tony’s exudes that unique funky charm. One notable feature is the large jewfish mounted above the entrance, which Captain Tony caught and preserved. It’s said that if you throw a quarter into the mouth of the fish, you’ll have good luck until you leave the island. The bar has also hosted many famous visitors over the years, including Ernest Hemingway, Truman Capote, and Jimmy Buffett, who immortalized it in his song “Last Mango in Paris.”

Captain Tony Tarracino: A Colorful Legacy

Captain Tony Tarracino, the bar’s namesake, wasn’t just a bar owner; he was a colorful character in Key West’s history. He served as the mayor of Key West from 1989 to 1991. Known for his larger-than-life personality, Tony was a former gunrunner, gambler, and avid storyteller. His life and adventures added to the legend of Captain Tony’s Saloon, making it not just a bar but a piece of living history.

Live Music and Entertainment

With live entertainment every afternoon and a live band every night, Captain Tony’s is one of the top dive bars in Key West. Its rich history, distinctive decor, and energetic music scene make it a must-visit.

The Green Parrot: A Key West Institution Since 1890

Location: 601 Whitehead St, Key West, FL 33040
Website: The Green Parrot

Since 1890, The Green Parrot has been a cornerstone of Key West’s live music scene, earning its status as “A Key West Institution.” This historic bar offers an eclectic atmosphere and a lively lineup of performances that make every visit unique and memorable.

Key West's Iconic Dive Bars & Watering Holes 2

Live Music and Community

What truly sets The Green Parrot apart and solidifies its reputation as one of the top dive bars in Key West is its dedication to live music and community. The bar is renowned for featuring an eclectic mix of local and touring bands, providing a stage for various genres and ensuring that there’s always something exciting happening. Its welcoming, no-frills vibe attracts both locals and tourists, making it a place where everyone feels at home. The Green Parrot features live music daily, with performances typically starting in the evening and going late into the night. They also have sound check at 5:30 PM, giving patrons a sneak peek at the night’s performances.

Unique Decor and Atmosphere

One of the most unique features of The Green Parrot is its sprawling parachute ceiling. The story goes that a former Army paratrooper donated his old parachute to the bar, and it was subsequently stretched across the ceiling, creating a colorful and eye-catching spectacle. The decor is equally eclectic, featuring an array of trinkets, taxidermy, and vintage memorabilia that make it a visual feast for patrons. This playful and colorful atmosphere makes the Green Parrot a must-visit destination for anyone seeking an authentic Key West experience. Photo credit: The Green Parrot.

Sloppy Joe’s: A Key West Tradition

Location: 201 Duval St, Key West, FL 33040
Website: Sloppy Joe’s

In the heart of Old Town, Sloppy Joe’s stands as a monument to Key West’s storied past and present. Proclaimed as “A Key West Tradition,” this legendary bar has been a favorite spot for locals and visitors since 1933. Known for its live entertainment, historic ambiance, and connection to literary giant Ernest Hemingway, Sloppy Joe’s embodies the spirited culture and festive soul of Key West.

Key West's Iconic Dive Bars & Watering Holes 3

Live Music and Entertainment

Sloppy Joe’s features live music every day from noon until 2:00 AM, with a mix of local and touring bands ensuring there’s always something exciting happening. The bar’s welcoming, no-frills vibe attracts a diverse crowd, from Hemingway enthusiasts to music lovers. This vibrant music scene is just one reason to visit, and the bar menu which includes the popular Sloppy Rita, adds to the overall experience. Photo credit: Sloppy Joe’s Bar.

Hemingway Days and Cultural Significance

Did you know? Sloppy Joe’s is home to the annual Hemingway Look-Alike Contest, where “Papas” from around the world gather to compete for the title of the best Hemingway look-alike, celebrating the author’s legacy and larger-than-life persona. The annual Hemingway Days festival, taking place from July 16-21, 2024, honors Hemingway’s life and works, drawing fans and participants from around the world to Sloppy Joe’s and other historic sites in Key West. In addition to the Look-Alike Contest, highlights include the whimsical Running of the Bulls, a fishing tournament, and various literary events, making it a cornerstone of the celebration. It’s a great way to celebrate this literary legend.

Celebrating Dive Bar Culture Every Day

While July 7th is National Dive Bar Day, in Key West, we celebrate it every day! These bars and watering holes are living history, each visit adding a new chapter to their storied past. Oh, if these walls could talk, imagine the stories we would hear. As you explore these iconic spots, remember you are part of a tradition that makes Key West so special. #somolife