16. Captain Tony’S Saloon
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 294-1838
Address: 428 Greene St.
Description: Just half a block off Duval, this watering hole is the site of Hemingway’s original bar stool and Key West’s first hanging tree, which grows through the roof of the bar. Captain Tony’s is part of Key West’s history, as it is the original location of Sloppy Joe’s. Once owned by Capt. Tony Tarracino, a friend of Jimmy Buffett’s and a former Key West mayor, the saloon features walls covered with bras and business cards. Live entertainment is offered nightly.
17. Chart Room Bar
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-4600 or (800) 327-83
Address: 1 Duval St.
Insider Pick:
Description: You want to experience a slice of Key West history? Step into this tiny bar located in the Pier House Resort and you will be stepping back in time. Tom Corcoran, author of the popular Alex Rutledge Key West mystery series, used to tend bar here while Jimmy Buffett played for tips. The bar has changed little since then, and the bartender can regale you with many a story about the duo.
18. Cowboy Bill’S Honky Tonk Saloon
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 295-8219
Address: 618 Duval St.
Insider Pick:
Description: The original owner of Cowboy Bill’s was a real-life cowboy on the rodeo circuit until he came to Key West. Mechanical bull and all, this urban cowboy turned tropical, and patrons are in for one wild ride! Open 7 days a week with happy hour daily, Cowboy Bill’s has a full menu for eats; a game room with pool, darts, and video games; and 24 TVs a-blaring. Boot scoot across the dance floor to live music, not to mention riding the mechanical bull. Hold on to those cowboy hats—this is not for amateurs!
19. 801 Bourbon Bar And Cabaret
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 294-9354
Address: 801 Duval St.
Description: With a clientele consisting of primarily gay patrons and tourists, 801 offers a first-floor bar with billiards. A second floor features live entertainment with Drag Queen Bingo at 5 p.m. every Sun and drag shows nightly, starring the world-famous Sushi. You might have seen her on CNN New Year’s Eve counting down the seconds to the new year while being lowered in a giant red high heel. She even managed to make Anderson Cooper blush.
20. Fat Tuesday
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-9373
Address: 305 Duval St.
Description: Stop in at Fat Tuesday and choose from one of 26 flavors of frozen drinks, including margaritas, piña coladas, and 190-octane rum runners. Our favorite is the Pain in the Ass, a combination piña colada and rum runner. The motto here is “One daiquiri, two daiquiri, three daiquiri, floor,” and you can even buy a T-shirt that says just that.
21. Finnegan’S Wake Irish Pub & Eatery
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 293-0222
Address: 320 Grinnell St.
Description: Exactly like a good Irish public house ought to be, Finnegan’s keeps the merriment going until nearly dawn (4 a.m.) and is among a mere handful of Key West establishments serving food into the wee hours (see the Restaurants chapter). You’re sure to find your Guinness here, and you can even down a black and tan. Order one and the barkeep will think you just returned from the Emerald Isle. Enjoy live Irish music on weekends and heed their motto: “Come for the food. Stay for the beer. Leave with the staff.”
22. Grand Vin
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-1020
Address: 1107 Duval St.
Insider Pick:
Description: Grand Vin is a locals’ top pick for its bar and wine shop. Not sure which wine suits you best? Sit at the bar and try a tasting flight of wine, three glasses of different varietals that will have your taste buds singing. Newly expanded seating on the porch and lower patio is great for people-watching through all hours of the day or night.
23. The Green Parrot Bar
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 294-6133
Address: 601 Whitehead St.
Insider Pick:
Description: Frequented primarily by locals, and known simply as “The Parrot,” this eclectic bar is housed in an 1890s-era building half a block off Duval, down Southard Street. Walls are adorned with unusual oversize portraits and a mural of the Garden of Eden. Weekends feature local and national bands playing everything from ukuleles in harmony to blues and zydeco, and the large dance floor is usually crowded.
24. Hard Rock Cafe
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 293-0230
Address: 313 Duval St.
Description: The Hard Rock Cafe joined the Conch Republic in the summer of 1996. Situated in a renovated, 3-story, Conch-style house on Duval Street, Hard Rock Cafe Key West celebrates historic Key West, the preservation of the Florida Keys’ fragile environment, and, of course, rock ’n’ roll. This 235-seat Hard Rock is open daily and serves up all-American fare.
25. Hog’S Breath Saloon
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-4222
Address: 400 Front St.
Description: The Hog’s Breath features an open-air mahogany bar surrounded by water-sports-related memorabilia, including mounted fish and surfboards. You can try the medium-bodied Hog’s Breath beer and sample one of the saloon’s famed fish sandwiches. The restaurant (see the Restaurants chapter) is open for lunch and dinner. Live bands play rock, folk rock, blues, and jazz throughout the day and well into the evening. You can purchase T-shirts, hats, and sundry other items emblazoned with the saloon’s slogan: “Hog’s Breath is better than no breath at all.”
26. Jimmy Buffett’S Margaritaville Cafe
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 292-1435
Address: 500 Duval St.
Description: Yes, the big man himself does play here once in a while, as do some of the Coral Reefers and bands that have opened for Jimmy on tour. Props from past concerts decorate the walls, ceiling, and even tables. Margaritas are just one of the many frozen drinks offered at the air-conditioned yet open-air bar. You can get a Cheeseburger in Paradise with all the fixin’s or pick up some Buffett clothing, recordings, books, and memorabilia at the shop next door (see the Restaurants and Shopping chapters). There is live music nightly, and keep your eyes open: Country singer-songwriter Kenny Chesney once performed here.
27. Joe’S Tap Room
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 294-5717
Description: Located upstairs behind the world-famous Sloppy Joe’s Bar (see listing in this chapter) on Duval Street, Joe’s Tap Room is another venue in this popular hangout. Large-screen TV and porch seating are available here. Doors blow open at noon, and they have NFL and college football on HDTV. Gives you a little “home away from home” feeling!
28. La-Te-Da
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-6706
Address: 1125 Duval St.
Description: La-Te-Da is a combination hotel, cabaret, restaurant, and bar that has been an icon of the Key West party scene since 1978. They not only offer a bar that faces lively Duval Street, but also live entertainment in their Cabaret Lounge. There is also a Terrace Bar overlooking the beautiful tropical pool. With the great island drinks and delicious food being served here, you may find it difficult to leave.
29. Martin’S
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 295-0111
Address: 917 Duval St.
Insider Pick:
Description: Hands down, Martin’s serves the best espresso martini in all of Key West. A favorite with the locals when they are looking to “play through” from happy hour into the wee hours, the espresso martini is tops at Martin’s, which makes it with different coffee liquors and no cream. Martin’s also offers a good selection of wines, beers, and other martinis to enjoy in their sleek open-air lounge.
30. Point 5
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-0669
Address: 915 Duval St.
Insider Pick:
Description: In its lofty aerie above the chic nine one five restaurant, the decor at Point 5 only enhances the drinks. The walls, ceilings, and floors are covered in fabulous Dade County pine, and the second-floor porch beckons you with its cool breezes: Submit to a cheese plate from the bar menu while relaxing at your table on the open-air porch overlooking Duval Street.