The iconic Green Parrot Bar has been a fixture of Key West since 1890, originally known as the Brownsville Saloon. Over the years, the establishment changed owners and names several times, and at one point even operated as a grocery store. The Great Depression ended and World War II began and the grocery store became The Brown Derby Bar, a bunker-like, air-conditioned hangout for submarine sailors stationed at the base only a block away.

After the Navy pulled out in the early 1970s, Key West became a haven for hippies, bikers, vagabonds, and free spirits of all kinds. At that point, the then owner, Judy Sullivan, astutely turned this former Navy hangout into an open-air hipster watering hole, renaming it The Green Parrot Bar. In 1983, Jim Bean bought the place and, 27 years later, teamed up with Key West stalwart and Philadelphia entrepreneur, Pat Croce, who transformed it into the Green Parrot Bar that we know today.

The bar is often called the "last little piece of old Key West," due to its historic nature and laid-back vibe, and has been featured in a number of films and TV shows, including the movie "SpongeBob SquarePants: Sponge Out of Water."

Not only the oldest and possibly the best dive bar in Key West, this place also has hands down the best live music, acknowledged as one of the best live music venues in the country by Rolling Stone magazine. You can almost always find some decent bands playing here, and there is something for everyone – from jazz/funk to reggae, rock, and more. The bar has a unique tradition called the "Soundcheck," where patrons can watch the soundcheck of the evening's musical act for free.

Inside, it has everything you would expect, from lots of artifacts on the walls to a pool table, a pinball machine, and a mixture of locals and tourists rubbing elbows while enjoying some great (affordable) mixed drinks. You must try their signature Root Beer Barrel shot, made with Root Beer Schnapps and beer!

Tip:
The Green Parrot Bar has a strict "no credit cards" policy, so be sure to bring cash if you plan to visit!
The 'back room' is cooler in temperature than the rest of the bar.

Hidden behind La Trattoria – one of Key West's best Italian restaurants – is a charming upscale cocktail bar called Virgilio's Bar. Named after its founder, Virgilio "V" Sanchez, who opened the establishment in 2007, this place specializes in sophisticated, handmade drinks like Mochatini, Cuervo Cosmo, Razzle Dazzle, Italian Lemon Drop, and a dozen or more types of martinis (the bartenders actually make them with a "sidecar" so they're a martini and a half). The selection of craft cocktails on offer is extensive, and all the drinks are made with the freshest possible ingredients and a focus on classic recipes.

In addition to drinks, they also serve the full menu from La Trattoria, so you can enjoy fantastic food as well. The small dance floor is often grooving to the talented artists playing late into the night.

The atmosphere at Virgilio's Bar is laid-back and casual, with indoor and outdoor seating available. The decor features an eclectic mix of vintage and modern elements, including exposed brick walls, tin ceilings, and a mural by local artist Rick Worth.

The bar is popular with both locals and tourists and has been featured in numerous publications, including the New York Times and Travel + Leisure.

Tip:
Try to plan your visit on a Martini Monday, when they offer all their delicious martinis for a special price.

The Bull and Whistle Bar is one of the most recognizable stops on Duval Street, known for its open-air setup and lively energy. It sits in a historic building in the heart of Old Town and is easy to spot thanks to its wraparound balconies and constant flow of people. The vibe is casual and social, with music, conversation, and the sound of Duval Street moving right through the space.

The bar is set across multiple levels, each with its own feel. Downstairs, the main bar area is busy and loud, especially later in the day, with bartenders serving quick drinks and groups gathering around the counter. A floor above, the Whistle Bar level gives a better view of the street below and tends to feel a little more breezy. The balconies are a big part of the experience, letting visitors watch the crowds pass by while staying right in the middle of the action.

One of the best-known features is the rooftop “Garden of Eden” sun deck, a clothing-optional bar that’s popular with visitors looking for something different. Even if that isn’t your cup of tea, the Bull and Whistle itself is still a classic Key West nightlife stop, especially for people who want a fun place to grab a drink, listen to music, and take in the Duval Street atmosphere.

Mallory Square is one of the best-known waterfront spots in Key West, set right along the harbor at the western edge of Old Town. It’s famous for its nightly Sunset Celebration, when locals and visitors gather to watch the sky change color over the water. During the day, the area feels open and relaxed, with views of boats, palm-lined edges, and the gentle movement of the tide. In the evening, it turns lively and social, with music, snacks, and people filling the open space near the seawall.

Start near the waterline and face outward toward the Gulf. Take a slow look across the harbor, where you’ll often see sailboats, tour boats, and cruise ships in the distance. Then turn slightly and watch the crowd as the sun gets lower-street performers set up along the main walkway, and food carts start drawing lines. If you want the best view, come to the square early and choose a spot closer to the water with a clear horizon and away from tall masts or poles that might block the sunset.

For photos, the best moment usually comes just before the sun disappears-keep the camera ready, and look behind you too, because the fading light often makes the buildings and faces glow.

Mallory Square is simple to visit, easy to reach, and hard to forget. Whether you stop by for a quick look during the day or stay for the full sunset routine, it’s one of those Key West places that captures the island’s energy in a single spot.

Captain Tony's Saloon is housed in a building that has a history as colorful as the town of Key West itself. First built in 1852, the property once served as a morgue, a wireless telegraph station, and later, as a bordello, and a bar popular with the Navy, known as the First National Bank Saloon. During Prohibition, it housed several speakeasies, the last of which was named The Blind Pig and specialized in gambling, women, and bootleg rum.

The location has a rather macabre story to it. There once was a hanging tree standing in its center that was used for public executions – several men are said to have been hung here for piracy. Supposedly, there are bodies still buried underneath the floor (several gravestones reportedly to be found somewhere near the pool tables area). They say the place is also haunted by the infamous "lady in blue" ghost.

In the 1930s, the joint was renamed Sloppy Joe's and is where Hemingway did most of his drinking, while in Key West. In 1968, Tony Tarracino (called Captain Tony), a local charter boat captain, purchased the property, idled for many years by that time, and named it Captain Tony's Saloon.

Eventually, the place has become a cultural icon in Key West, patronized by many well-known artists, writers, and celebrities. A peculiar feature at the bar is that whenever a celebrity guest visits, a bar stool is added with that patron's name on it. Among those whose names have been inscribed on stools at Captain Tony's over the years are Truman Capote, Jimmy Buffett, Shel Silverstein, John Prine, John F. Kennedy, Harry Truman, Bob Dylan, and, of course, Ernest Hemingway himself.

Known for its quirky decor and unique atmosphere, the bar is filled with memorabilia, including license plates, bras, and countless dollar bills and bras hanging from the ceiling. With so much history, this is definitely a spot worth checking out… if you don't mind drinking while standing on someone's grave, that is.

Tip:
Above the sign outside the building is a large Jewfish that Captain Tony caught and preserved. It is said that if you throw a quarter into its mouth, good luck will follow you until you leave the island.

Anyone looking for a great place to grab a drink and have an awesome time in a fun and lively setting should consider Irish Kevin's Bar a definite must. Loud, funny, and energetic, this spot in the Old Town of Key West serves tonnes of booze mixed up with daily performances by local musicians and plenty of Irish charm to boot.

The bar was founded in 1998 by Kevin and Mary O'Sullivan, who came from Ireland. The couple wanted to create a place that would celebrate their Irish heritage while also embracing the laid-back vibe of Key West. Pursuant to this goal, the interior of the bar has been decorated with various Irish-themed items, including flags, posters, and memorabilia. Irish Kevin's also has a large outdoor seating area, which is perfect for enjoying a drink and people-watching.

Speaking of drinks, they have a great selection of draft beers, including traditional Irish brews like Guinness, as well as local favorites like Key West Sunset Ale, plus some whiskeys like Jameson.

One of Irish Kevin's main draws is the interactive show, which takes place every day of the week. During the show, the performer invites people on stage and encourages the crowd to participate in various chants, sing-alongs, and other activities. The crowd itself is pretty diverse, with some being on the younger side and some not quite right out of college, but everyone mixes in well and seems to get along great.

Over the years, the bar has been featured in numerous travel guides and won several awards, including Best Live Music Venue in Key West. In 2005, its popularity was boosted further when the place appeared on the Travel Channel show "World's Best Bars."

Tip:
You'll find some amazing finds in the gift shop, including shot glasses, T-shirts, bar signs, etc.

The Rick's Entertainment Complex is the largest drinking establishment in Key West and, indeed, a one-stop party spot for all of the Florida Keys, having eight different venues under one roof.

If you enjoy live music while sipping a cold beverage during the day, or wish to live out your rock star dream at night, you can have all that at Rick's Downstairs, also known as the Karaoke Bar.

At Durty Harry's, you can catch live performances by some of the island's most talented musicians seven nights a week, or watch sports on one of the 15 TV sets throughout the bar (or a larger 10-foot screen, for that matter), whilst enjoying tasty cocktails, ice beer, and good tunes. Alternatively, you can pull up a stool at the hand-carved wooden Tree Bar, shaded by a giant Monkey Pistol tree on the street level, and enjoy the refreshing blends of premium liquors with fresh juices squeezed by hand along with people-watch!

Rick's Upstairs – a place to see and be seen; it offers a fusion of high energy and a chill atmosphere. Here, you can sip on a cocktail sitting on the balcony overlooking the world-famous Duval Street down below or dance the night away on the Florida Keys' biggest dance floor. With its state-of-the-art laser and light show, and a DJ spinning today's hottest hits, this joint has something for everyone!

The premier gentlemen’s club – The Red Garter Saloon – is the place for those keen on the company of lovely ladies. For visitors' enjoyment here are Champagne Rooms and a VIP area. And if you want to get away from the crowd, The Crow's Nest (in Durty Harry's) is sufficiently tucked away from it all.

The island nights often get steamy. Whenever there's a need to cool it down a bit with a frozen treat, you can try out The Mardi Gras frozen daiquiri bar offering a wide selection of liquors and beers coupled with a great view of the Durty Harry's courtyard.

Finally, if it's time to sneak away to a quiet corner, or if you have a special event coming up, The Loft is a perfect place to consider, offering a touch of sophistication: cool marble floors, soft leather couches, and comfortable air conditioning to keep you coming back.

Sloppy Joe's Bar is a historic drinking spot in Key West, Florida, whose colorful past stretches way back to 1933. The bar's owner, Joe Russell, ran a speakeasy during the Prohibition era. When it was over, he opened a small drink stand originally known as "The Blind Pig".

The joint quickly gained popularity among locals for its lively atmosphere and cheap drinks and, over the years, played host to a number of notable patrons and events. It was a favorite haunt of writer Ernest Hemingway, who lived in Key West for many years and was a regular here. In fact, it was Hemingway who suggested that the bar changed its name to Sloppy Joe’s through association with his favorite watering hole in Havana, Cuba, which bore the same moniker (for being owned by one Jose Garcia), that he felt would suit this place just as well – and it did.

In 1937, following a quarrel with the landlord, Russell moved the establishment to its current location at the corner of Duval and Greene streets, where it has remained ever since. Today, Sloppy Joe's is still going strong, as it was in the days of Hemingway, and remains one of the most popular gathering spots in Key West.

It's an old but fun space, full of tourists and live music, so be encouraged to grab a few drinks here, as they're stronger and cheaper than most others in the area (you will even find that they serve Kenny Chesney's line of rums – Blue Chair Bay). The Caribbean-American comfort food is really good, too, so have at least one meal here during your trip. While at it, take some time to look around and you will notice all the historic photos, including lots with Ernest Hemingway, their most famous patron.

Although not exactly the same place frequented by Hemingway, Sloppy Joe's continues to celebrate the life of the great author with the Annual Hemingway Look-Alike Contest every July. As for the original Hemingway location nearby, it is currently occupied by Captain Tony's Saloon.

Note:
They always ask to see your photo ID along with your credit card, when paying the bill, as a precautionary fraud measure.

If you're a dive bar sort of person who enjoys a totally chill, unsophisticated, grungy atmosphere with live music and surprisingly good food, this is the spot.

The Schooner Wharf was originally located on board the Schooner Diamante. It moved ashore in 1984 and was housed in a former shrimp packing warehouse that was renovated to create a rustic and inviting ambiance. For this purpose, the walls have been covered in nautical decor, including old fishing nets, buoys, and flags.

Over the years, the bar has evolved into a very special place, expanded into a neighboring building, and added a second-floor deck with a panoramic view of yacht decks, magical sunsets, and Key West's Historic Seaport. A staple of the local community, this popular waterfront joint is now probably the hottest bar on the shore of Key West and has been featured in articles by The NY Times and Aqua Magazine.

The Schooner Wharf serves a variety of drinks and food, including fresh seafood, burgers, and sandwiches. Its signature drink is the Rumrunner, a tropical cocktail made with rum, fruit juice, and grenadine. Customers can enjoy their food and drinks while sitting at the bar, on the outdoor deck, or the pier overlooking the water.

The bar hosts live music shows almost every night of the week, featuring local musicians playing a variety of genres including rock, country, and blues. The nights when Michael McCloud is there with his band deserve a particular note. There are also special events throughout the year, such as the annual Conch Republic Independence Celebration in April and the Lighted Boat Parade during the holiday season.

A great place to linger after walking all day.