Key West Bar Hopping, Key West

Key West Bar Hopping (Self Guided), Key West

Referred to as "an amusement park for adults fueled with alcohol", Key West has so many great bars, each with their own vibe, that it's hard to narrow it down to just a few – but the ones included in this walk should get you off to a good start. Besides a sense of history and exceptional sunsets, the bars offer good beers, margaritas, wines, a variety of meals, and – not the least important – good live acts. So hold on as we set sail for Florida's tropical paradise and hop between its many temptations.
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Key West Bar Hopping Map

Guide Name: Key West Bar Hopping
Guide Location: USA » Key West (See other walking tours in Key West)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 8
Tour Duration: 1 Hour(s)
Travel Distance: 1.3 Km or 0.8 Miles
Author: vickyc
Sight(s) Featured in This Guide:
  • Green Parrot Bar
  • Virgilio's at La Trattoria
  • Bull and Whistle Bar
  • Irish Kevin's Bar
  • Rick's Entertainment Complex
  • Sloppy Joe's Bar
  • Captain Tony's Saloon
  • Schooner Wharf Bar
Green Parrot Bar

1) Green Parrot Bar

Not only the oldest and possiby the best dive bar in Key West, this place also has hands down the best live music. You can almost always find some of the better bands playing here, and there is something for everyone – from jazz/funk to reggae, rock and more. Inside it is everything you would expect with lots of artifacts on the walls, 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 the signature Root Beer Barrel shot, made with Root Beer Schnapps and beer!

The 'back room' is cooler in temperature than the rest of the bar.

Opening Hours:
Daily: 10am–4am
Happy Hour: 4–7pm
Virgilio's at La Trattoria

2) Virgilio's at La Trattoria

Hidden behind La Trattoria – one of Key West's best Italian restaurants – is this charming upscale bar specializing 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 "side car" so they're a martini and a half). They also serve the full menu from La Trattoria, so you can enjoy fantastic food and drinks as well as a variety of music during the week. The small dance floor is often grooving to the talented artists playing late into the night.

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

Opening Hours:
Mon-Fri: 10am–10pm; Sat, Sun: 11am–12am
Bull and Whistle Bar

3) Bull and Whistle Bar

One of Old Town Key West's oldest establishments, the Bull harks back to the seafaring days of yore. It's always a good place to sit and pass the time sipping on a favorite beverage, enjoying live music, and watching people stroll by. Despite being an open-air bar, they somehow managed to have hand-painted murals all around, which is quite visually stimulating.

The 2nd-floor Whistle Bar has pool tables, a nice casual atmosphere, and a balcony overlooking Duval Street; also, if you're brave enough, there's a 3rd-floor clothing-optional "Garden of Eden". Rolling Stone magazine's "best-kept secret in Key West", the Garden offers great views, live bands, body painting, and a few brave souls in their birthday suits.

Opening Hours:
Daily: 9am–3:30am
Irish Kevin's Bar

4) Irish Kevin's Bar

Loud, funny, energetic and entertaining, Irish Kevin's in Old Town is a great place to grab a drink and have an awesome time. The live entertainers here are not content with singing only, but also bring the crowd into the fun by asking for participation and even inviting people on stage. Some music you will be asked to sing along to, while other times you'll just listen and watch. The service is quite attentive and the drinks are good, with a great selection of draft beers and some whiskeys, as well. The crowd 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.

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

Opening Hours:
Daily: 10am–3:30am
Rick's Entertainment Complex

5) Rick's Entertainment Complex

The Rick's Entertainment Complex is the one-stop party spot for all of the Florida Keys! With eight different venues to choose from, they have something for everyone. Whether it's dancing upstairs, listening to the Keys favorite rock band in Durty Harry's, singing karaoke, or hanging out with the lovely ladies of the Red Garter, this place has it all. The entertainment is always great, off the wall and something you can only enjoy in Key West where anything flies.

The several stools fenced in by the street have their own bar window, making this a great spot during the day to squeeze in, grab a drink and people-watch.

Opening Hours:
Daily: 11am–4am
Sloppy Joe's Bar

6) Sloppy Joe's Bar

Located at the corner of Duval and Greene streets since 1937, Sloppy Joe's is a Key West institution and piece of history that you'll have to stop in while visiting town. It's an old but fun space, full of tourists and local live music, so grab a few drinks as they're stronger and cheaper than most other 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 doing so, take some time to look around and you will notice all the historic photos, including lots with Ernest Hemingway, their most famous patron, who suggested the name of Sloppy Joe's in honor of one of his favorite bars in Havana, Cuba, which was owned by one Jose Garcia. Overall, this is a fun, unique stop on any and every trip to Key West!

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

Opening Hours:
Mon-Sat: 9am–4am; Sun: 12pm-4am
Captain Tony's Saloon

7) Captain Tony's Saloon

The original location of Sloppy Joe's, this is where Hemingway did most of his drinking when he lived in Key West. Apart from the live entertainment and signature drinks, an interesting feature of the bar is that when any celebrity visits, a bar stool is added with that patron's name. Among other stools here, you will find those painted with the names of Truman Capote, Jimmy Buffett, Shel Silverstein, John F. Kennedy, Harry Truman and, of course, Ernest Hemingway himself.

The place itself is said to be haunted by the infamous "lady in blue" and has a rather macabre history – look for a hanging tree inside (used to hang several for piracy) and a few gravestones by the pool tables. Supposedly there are bodies still buried under the floor as well. With so much history, plus the countless dollar bills and bras hanging from the ceiling, this is definitely a place worth checking out… if you don't mind drinking while standing on someone's grave.

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

Opening Hours:
Daily: 10am–2am
Schooner Wharf Bar

8) Schooner Wharf Bar

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. Schooner Wharf is probably the hottest bar on the shore of Key West, having been featured in articles by The NY Times and Aqua Magazine. With a panoramic view of yacht decks, magical sunsets, and Key West's Historic Seaport, it offers excellent seafood, drinks and music (especially when Michael McCloud is there playing with his band) along with a fantastic dancefloor in its unique nautical decor. A great place to linger after walking all day.

Opening Hours:
Daily: 7am–4am

Walking Tours in Key West, Florida

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