Updated at: 01-10-2023 - By: John Lau

If you’re looking for a laid-back night out in Key West, dive bars are the way to go. These watering holes offer a casual atmosphere, cheap drinks, and a chance to mingle with locals and tourists alike.

In this article, we’ll take a look at some of the best dive bars in Key West, including classic spots like The Green Parrot and Captain Tony’s Saloon, as well as lesser-known gems like The Chart Room and Schooner Wharf Bar.

Whether you’re in the mood for a game of Ship, Captain, Crew or just want to enjoy a cold beer by the water, these dive bars are sure to hit the spot. So grab a drink, kick back, and let’s dive into the best dive bars in Key West.

Top 13 Best Dive Bars Key West

The Green Parrot

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The Green Parrot is a popular local dive bar in Key West, Florida. It has been an institution since 1890 and is known for its casual atmosphere, great drinks, and frequent live music. The bar has been named one of the Top Twenty Bars in America by Playboy magazine. The Green Parrot is located at 610 Whitehead St in Key West. It started as a corner grocery store/bar and has a rich history. If you’re looking for a classic Key West saloon, the Green Parrot is a must-visit spot.

Captain Tony’s Saloon

Captain Tony’s Saloon is a historic bar located at 428 Greene Street in Key West, Florida, United States. The building that houses the saloon has a colorful history, dating back to its construction in 1852 as an ice house and city morgue. In the 1890s, it served as a wireless telegraph station, with its most significant use during the Spanish-American War, when news of the destruction of the battleship Maine was reported from this building.

The bar has been frequented by many well-known artists, writers, and celebrities over the years. One of its most famous patrons is Jimmy Buffett, who got his start in Key West by playing at Captain Tony’s in the early 1970s. Buffett even immortalized the bar and its owner, Captain Tony Tarracino, in his song “Last Mango in Paris”. On occasion, Jimmy Buffett has made surprise appearances at the bar.

Captain Tony’s Saloon is known for its old-school pub atmosphere and is a popular spot for locals and tourists alike. It offers live music, strong drinks, and friendly service, making it a favorite among visitors to Key West. The bar’s central location on Duval Street in old Key West adds to its appeal.

Chart Room

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The Chart Room is a small, dimly lit bar located in the Pier House Resort in Key West. It is a dive bar with only six bar stools, and it is known for its laid-back atmosphere.

The bar serves wine, which is either red or white, and popcorn. The Chart Room is a hidden treasure in Key West, and it is especially popular among fans of Jimmy Buffett and the island’s pirate history.

The bar has a long and interesting history, and it is a modern-day pirates’ paradise. The Chart Room is a great place to visit if you are looking for a unique and authentic Key West experience.

Schooner Wharf Bar

Schooner Wharf Bar is a popular open-air hangout in Key West, Florida, known for its seafood, live music, and dockside views. It has been voted the best bar in the People’s Choice Awards since 1993. The bar is located at 202 William Street and offers a unique and funky atmosphere, reminiscent of old Key West before the rise of million-dollar condos.

The menu at Schooner Wharf Bar features a variety of breakfast, lunch, and dinner options, as well as a special party menu for catering. The bar is also known for its three daily happy hours. Some of the standout dishes include impeccably fresh oysters and shrimp, flavorful and spicy chowder, and fritters that are actually worth eating. The mojo-marinated fish sandwich is also highly recommended.

The bar is a favorite among locals and visitors alike, and its eclectic mix of customers, including their pets, adds to its charm. The sounds of the best musicians in the Keys can be heard at Schooner Wharf Bar, making it a great spot for live entertainment. The bar has a small stage and umbrella-covered tables set on a gravel patio.

Schooner Wharf Bar is also the home port of the Key West flagship Schooner Western Union, a 130-foot-long tallship that is available for sunset cruises and private parties. The bar has expanded into a neighboring building and added a second-floor deck with a beautiful view of the classic yachts of Key West’s Historic Seaport, which is also available for private parties.

The owners of Schooner Wharf Bar, Evalena and Paul Worthington, are planning to host a classic wooden boat show in the near future, following extensive renovations to their 46-foot, 1930 Dawn motor launch “Coquille,” which is available for short trips and harbor tours.

The Dive Bar Shirt Club

The Dive Bar Shirt Club is a unique establishment located at 320 Grinnell Street in Key West, Florida. It is possibly the world’s first Dive Bar-Tee Shirt Club, where vintage beer paraphernalia creates a unique atmosphere in one of old town Key West’s most iconic buildings. The Dive Bar Shirt Club serves draft beers, wine, and seltzers accompanied by a snack menu with tacos and chips. According to the Key West Bar Card website, you can get your first round buy one, get one free with your Key West Bar Card.

The Dive Bar Shirt Club is also a monthly subscription service. By becoming a member, you will receive an authentic T-shirt from the best of America’s most interesting and unusual bars every month. The T-shirts are from the best dive bars in the world that you may or may not have heard of.

In summary, The Dive Bar Shirt Club is a unique establishment in Key West, Florida that serves draft beers, wine, and seltzers accompanied by a snack menu with tacos and chips. It is also a monthly subscription service that sends you an authentic T-shirt from the best dive bars in the world every month.

Bobby’s Monkey Bar

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Bobby’s Monkey Bar is a popular establishment in Key West, Florida, known for its laid-back atmosphere, strong drinks, and friendly bartenders.

– Location: 900 Simonton St, Key West, FL 33040.

– Contact: (305) 294-2655.

– Hours: Open daily from 12:00 pm to 8:00 pm.

– Features: Bike parking, good for happy hour, has TV.

– Atmosphere: The bar is described as low-key, with a chill vibe. It is a popular spot for both locals and visitors.

– Drinks: Bobby’s Monkey Bar is known for its cheap drinks and strong pours.

– Entertainment: The bar offers karaoke nights, which are well-received by patrons.

– Unique Decor: Inside the bar, you’ll find dozens of Velcro-handed monkeys dangling from the chandeliers and rafters, adding a playful touch to the ambiance.

If you’re in Key West and looking for a relaxed spot to enjoy a drink, Bobby’s Monkey Bar is worth checking out.

Bert’s Bar

Bert’s Bar is a bar and restaurant located in Key West, Florida. Here is some information about Bert’s Bar based on the search results:

– Location: Bert’s Bar is located at 213-217 Duval St, Key West, FL 33040.

– Atmosphere: According to one review, Bert’s Bar has an “awesome atmosphere”.

– Menu: The menu for Bert’s Bar is available online.

– Features: Bert’s Bar has bike parking, outdoor seating, and TVs.

– Reviews: Bert’s Bar has received positive reviews on Yelp, Restaurant Guru, and Restaurantji.

Mary Ellen’s Bar & Kitchen

Mary Ellen’s Bar & Kitchen is a neighborhood bar and restaurant located in Key West, Florida. It is open daily from 11am-4am, 365 days a year. The bar has a cool vibe and serves comfort food, including gourmet grilled cheese.

The menu is available for delivery or pick up, and can be viewed on their website. In addition to food and drinks, Mary Ellen’s also hosts events, which can be found on their event calendar. Photos of the bar can also be viewed on their website.

The address of Mary Ellen’s Bar & Kitchen is 420 Appelrouth Lane, Key West, FL 33040-6535.

Hog Heaven Sports Bar & Grill

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Hog Heaven Sports Bar & Grill is a popular restaurant located in Islamorada, Florida, known for its hearty portions of delicious BBQ, fresh seafood, sandwiches, burgers, and more. The restaurant offers both indoor and outdoor bars, live music, and DJ weekends, making it a great spot for entertainment. Here are some highlights of the menu and the overall dining experience at Hog Heaven Sports Bar & Grill:

– Menu: The lunch and dinner menu at Hog Heaven features a variety of tasty starters, including Pig Candy, Pig Wings, Conch Fritters, Cheese Nachos, Loaded Nachos, Buffalo Chicken Dip, Smoked Fish Dip, and Brisket Deviled Eggs. In addition to these appetizers, the restaurant offers a wide selection of main dishes, such as BBQ, seafood, sandwiches, and burgers.

– Dining Experience: Visitors to Hog Heaven Sports Bar & Grill have praised its unique atmosphere, describing it as a combination of a sports bar, island resort, biker bar, and BBQ joint. The restaurant is tucked away in a protected ocean cove in sleepy Islamorada, making it a hidden gem in the Upper Keys. It is also the only late-night spot in the area, making it a popular destination for those looking for entertainment after hours.

Key West First Legal Rum Distillery

The Key West First Legal Rum Distillery is a popular attraction in Key West, Florida, offering tours, tastings, and mojito classes on the site of a former saloon.

The distillery is located at 105 Simonton Street, in a building that was previously the Coca-Cola bottling plant from 1903 to 1983.

The distillery offers free tours daily from 12 pm to 5 pm, where visitors can learn about the history of Key West and the rum-making process. Free tastings are also available, allowing visitors to sample the distillery’s award-winning Chef Distilled American Rum.

In addition to tours and tastings, the distillery offers mojito classes, where participants can learn how to make this classic rum cocktail.

The distillery was founded in 2013 by Chef Paul Menta, who used demerara sugar and homemade extracts to create what is described as the best and smoothest rum in Key West.

The Key West First Legal Rum Distillery has received positive reviews and is considered one of the best distilleries in Key West.

 The Cabaret At La Te Da

La Te Da is a hotel in Key West that offers low-key lodging for over-21s only. The hotel features a pool, a restaurant, and an on-site cabaret that is renowned for first-class entertainment.

The Cabaret at La Te Da is a Key West landmark that has been around for over 30 years. The cabaret features original shows from top performers such as Christopher Peterson and Randy Roberts. The schedule for the cabaret can be found on the La Te Da website.

One of the most popular events is the infamous Tea Dance, which takes place every Sunday at La Te Da and features music and dancing with resident DJs Rude Girl and Molly Blue. Visitors can also check out reviews of The Cabaret At La Te Da on TripAdvisor and Yelp.

Sunset Pier

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Sunset Pier is a bar and restaurant located at the Ocean Key Resort & Spa in Key West. It is a relaxed dockside seafood eatery with water views, drinks, and live music.

The pier extends 200 feet over the water, providing a vibrant and view-boasting space for a truly memorable island event. Sunset Pier has received positive reviews on TripAdvisor, with a rating of 4.5 out of 5 stars and 1368 reviews.

Visitors can enjoy a Key West Sunset Sail Aboard Schooner, a 2-Hour Private Sunset Cruise around Key West, or a Sunset Tiki Boat Tour in Key West.

Sunset Pier is open from 11:00 AM to close and offers a variety of drinks and food options.

Tipsy Rooster

Tipsy Rooster is a quirky liquor store and bar located in Old Town Key West. It features outside tables, live music nights, and a selection of spirits for sale.
The bar offers specialty drinks, including horseradish-infused vodka, locally made pepper pot tamarind and Key West jerk seasoning, olive juice, and zing zang bloody mary mix.

Tipsy Rooster is open from 10:00 am to 1:00 am from Monday to Wednesday.

It is a popular spot for locals and tourists alike, and it has been voted the #1 BEST Liquor Store in Key West.