While New Orleans holds a special place in the hearts of many revelers, Key West undeniably stakes a claim as one of America’s premier party destinations. The allure is multifaceted: consistently pleasant weather, a welcoming atmosphere fostered by friendly locals, the generous pours and enticing happy hour deals, and a pervasive sense of safety and fun. With a staggering array of watering holes, conquering all of Key West’s bars in a single night – or even two – proves an impossible feat, but the sheer abundance invites exploration and spirited attempts. This guide highlights twelve exceptional establishments that capture the essence of Key West’s vibrant bar scene.
1. Sloppy Joe’s
A cornerstone of Key West’s social fabric, Sloppy Joe’s, established in 1933 and situated at its current address since 1937, resonates with historical significance. Once a favored haunt of Ernest "Papa" Hemingway and his entourage, it remains a beloved and consistently entertaining venue. Expect a lively atmosphere, even on off-season weeknights, as the spacious stage hosts some of Old Town’s most talented bands. Live music pulsates until 2 a.m., and the high ceilings contribute to surprisingly good acoustics. For a more relaxed experience, consider visiting in the late afternoon to avoid the peak crowds or venturing into Joe’s Tap Room, which offers a curated selection of draft beers.
Address: 201 Duval St, Key West, FL 33040, USA
Phone: +1 305-294-5717
2. The Hog’s Breath Saloon
Tucked away and retaining a hint of rugged charm, The Hog’s Breath Saloon manages to preserve its biker bar vibe despite its popularity with tourists. Patrons are encouraged (and often do) to dismount their motorcycles and settle in for a drink at the open-air bar. Embracing the Key West spirit, live bands and bikini contests are staples of the entertainment lineup. No visit is complete without acquiring a Hog’s Breath Saloon T-shirt, emblazoned with the bar’s iconic motto: "Hog’s Breath is Better Than No Breath at All." This is truly one of the best bars in Key West.
Address: 400 Front St, Key West, FL 33040-6617, USA
Phone: +1 305-296-4222
3. The Bull and Whistle
The Bull and Whistle presents a unique concept: two distinct bars housed within a single building (or three, if you include the rooftop Garden of Eden). The Bull, located on the ground floor, features a prominent central bar and a small stage for live performances. Ascend to the second floor to discover The Whistle, a sports-oriented bar equipped with a pool table, dartboard, and other classic bar games. The highlight of either space is undoubtedly The Whistle’s narrow second-floor veranda, lined with stools that provide patrons with a prime vantage point for observing the bustling street scene below while enjoying their drinks. This multifaceted establishment offers daily live music and captivating artwork that depicts the history, icons, and events that define the magic of Key West.
Address: 224 Duval St, Key West, FL 33040, USA
Phone: +1 305-296-4545
4. The Garden of Eden
Perched atop The Bull and Whistle, The Garden of Eden offers a distinctly different experience as Key West’s only clothing-optional bar. This rooftop oasis, adorned with lush tropical foliage and shielded from street-level views, invites patrons to embrace a sense of liberation. The level of exposure varies depending on the day, time, and weather. Expect a topless bartender (serving drinks that are slightly pricier than elsewhere in town), and on sunny afternoons, nude sunbathers lounging on deck chairs. While nudity is not mandatory, body paint offers a creative way to express oneself without fully disrobing. Photography is strictly prohibited to ensure the privacy and comfort of all guests.
Address: 224 Duval St, Key West, FL 33040, USA
Phone: +1 305-296-4545
5. Capt. Tony’s Saloon
Historically significant as the original location of Sloppy Joe’s (before a rent dispute prompted its relocation), Capt. Tony’s Saloon served as Hemingway’s Key West haven for many years. The bar is steeped in local lore, with artifacts and stories adorning the walls. The very tree you might be leaning against with your drink was once Key West’s "hanging tree" in the 19th century, potentially placing you in the company of spectral pirates who met their demise at the hands of local vigilantes. Capt. Tony’s Saloon hosts live music every night, adding to its vibrant atmosphere.
Address: 428 Greene St, Key West, FL 33040, USA
Phone: +1 305-294-1838
6. The Smallest Bar
True to its name, The Smallest Bar is an exceptionally compact establishment. The interior measures a mere 72 square feet (roughly the size of a jail cell), limiting occupancy to around 10 people. While seating is limited to three barstools, this intimate space is perfect for a small group of friends seeking a unique experience. Its location on Duval Street ensures constant interaction with curious passersby. Situated across from the Smallest Bar Inn (a standard-sized hotel), this miniature bar offers a memorable and quirky stop on any Key West bar crawl.
Address: 124 Duval St, Key West, FL 33040, USA
7. Margaritaville Key West
While not the largest or most elaborate of Jimmy Buffett’s Margaritaville chain, Margaritaville Key West holds the distinction of being the first, established in 1985. Located behind a distinctive pink façade at 500 Duval St., Margaritaville Key West features a stage for live bands and the signature tiki-bar décor. The menu offers a range of dining options and specialty drinks, including locally inspired dishes like conch fritters and key lime pie. Specialty cocktails are available in either a standard 22-ounce glass or a souvenir blender cup. While the drinks are pricey (around $18), they are crafted with a generous blend of liquors and juices. A must-visit for any Parrothead or anyone seeking a dose of laid-back, good-times vibes.
Address: 500 Duval St, Key West, FL 33040, USA
Phone: +1 305-292-1435
8. Hard Rock Cafe Key West
While local bars often dominate "best of" lists, the Key West Hard Rock Cafe merits inclusion due to its meticulous restoration of a beautiful three-story Victorian home in the heart of Duval Street. The brand has embraced its historic location, even hinting at a resident ghost on its website. Visitors can admire rock memorabilia, raise a toast to their musical heroes on the balcony, relax in the outdoor seating area, or try to catch a glimpse of the restless spirit of Robert Curry.
Address: 313 Duval St, Key West, FL 33040, USA
Phone: +1 305-293-0230
9. The Schooner Wharf Bar
Nestled within Key West’s historic harbor, The Schooner Wharf Bar caters to boaters and tourists alike, attracting notable figures such as Al Jardine of the Beach Boys and the late Charles Kuralt. The bar’s nautical theme is reflected in its specialty drinks, including the "Schooner Lemonade," rumrunners, and mango daiquiris. The Schooner Wharf Bar stands out with its generous offering of three distinct happy hour periods: 8 a.m. to noon, 5 p.m. to 7 p.m., and 2 a.m. to 4 a.m. A sunset cruise followed by Dark ‘n’ Stormy cocktails on the deck provides an idyllic experience. This is why The Schooner Wharf Bar is one of the best bars in Key West.
Address: 202 William St, Key West, FL 33040-6645, USA
Phone: +1 305-292-9520
10. The Rum Bar
Located within the Speakeasy Inn on Duval Street, The Rum Bar is overseen by Bahama Bob Leonard, a revered Key West figure and world-renowned rum expert. Classic tropical cocktails, such as the painkiller, mojito, and rum runner, are meticulously crafted at this hidden gem for rum aficionados. Leonard is also adept at introducing patrons to hidden treasures from his extensive collection of over 350 rums from the Caribbean and beyond.
Address: 1117 Duval St, Key West, FL 33040, USA
Phone: +1 305-296-2680
11. The Green Parrot
The Green Parrot, a lively corner bar, is an essential stop on the route to or from the Hemingway Home. Popular among locals and tourists alike, this eclectic bar has undergone several transformations throughout its history but remains a beloved destination for exceptional music and camaraderie in Key West. The walls are adorned with signs, memorabilia, and an assortment of eclectic items, each with a unique story to tell. Open seven days a week, The Green Parrot hosts live music performances almost daily, ranging from country bands to brass punk rock.
Address: 601 Whitehead St, Key West, FL 33040, USA
Phone: +1 305-294-6133
12. Irish Kevin’s
This Duval Street Irish bar features weekly live performances by Irish Kevin himself, an immigrant who settled in Key West in 1992 and established a pub on Duval Street. Irish Kevin’s boasts an impressive selection of beers on tap and encourages guests to sing along with Irish Kevin and other performers, potentially becoming part of the show. For those unable to attend in person, the bar offers a live stream of performances on its website.
Address: 211 Duval St, Key West, FL 33040, USA
Phone: +1 305-292-1262
