31. The Porch
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 517-6358
Address: 429 Caroline St.
Insider Pick:
Description: Locals head to the Porch, located behind door number 2 in the beautiful Porter Mansion on Caroline and Duval, for craft beers on tap and wine by the glass or bottle. Seasonal selections and popular events like regular wine tastings, 1920s costume parties, and DJ nights are also part of the fun. Beers on tap include Chimay Blonde Trappist Ale, Magic Hat #9, and Shipyard Export Ale, among others.
32. Rick’S Key West
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-5513
Description: Rick’s Key West offers eight nightspots in one complex, including a wine and martini bar, a dance club, a VIP bar, and a daiquiri bar. In addition, Rick’s Downstairs Bar offers live entertainment from 4 p.m. until midnight. The Tree Bar allows you to sit and sip a spell, all the while watching the sights of Duval Street pass by. The band at Durty Harry’s starts at 8 p.m. and plays live rock ’n’ roll until 4 a.m. This bar also has a television wall, which shows all major sporting events. And for a little more risqué entertainment, the Red Garter Saloon is a mirror-and-brass adult club. Pick your pleasure.
33. Schooner Wharf Bar
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 292-3302
Address: 202 William St.
Description: Dockside at the Key West Historic Seaport is the open-air, thatched-palm Schooner Wharf, which bills itself as “a last little piece of old Key West.” The place offers outdoor thatched-umbrella tables, a covered bar, grill, and indoor games, including billiards and darts. Live jazz, rhythm and blues, and island music are featured nightly.
34. Sloppy Joe’S Bar
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 294-5717
Address: 201 Duval St.
Description: It’s no wonder this was Hemingway’s favorite watering hole. The upbeat atmosphere of Sloppy Joe’s is contagious. The bar opened in 1933 on the site of what is now Captain Tony’s Saloon. In 1937 it moved to its current location. Some say that Hemingway did some writing in the back rooms of the bar and kept a few of his manuscripts locked up here. Photos of the author line the walls. Live entertainment is offered from noon to 2 a.m. daily. A gift shop sells T-shirts, hats, and other Sloppy Joe’s souvenirs.
35. Sports Page Bar And Grille
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-3230
Address: 610 Greene St.
Description: Watch the game of your choice on one of the eight TVs, two of which are projection, or shoot a game of pool while enjoying some jalapeño poppers, cheese fries, or potato skins. If the big game is on, the Sports Page is the place to be.
36. The Top
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-2991
Address: 430 Duval St.
Description: High above the city of Key West, with views of Key West Harbor as well as up and down Duval Street, this eagle’s-eye perch is one of the most famous bars in all the Keys. The Crowne Plaza Key West La Concha (see Accommodations chapter) was the first upscale lodging facility in the area, and to accommodate its infamous and famous clientele, this bar was developed. Rumor has it Hemingway romanced Ava Gardner and Marlene Dietrich at La Concha and spent many nights high in the sky here at this bar.
37. Turtle Kraals Restaurant And Bar
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 294-2640
Address: 231 Margaret St.
Description: The lounge portion of this turtle-cannery-turned-restaurant rocks throughout the evening, offering live entertainment (in season) and billiard tables in an open-air, waterfront setting (see the Restaurants chapter). Turtle Kraals’s full bar is known for its frozen margaritas, microbrewed beers, and imported beers on tap.
38. Virgilio’S
City: Florida Keys, FL
Category: Nightlife
Telephone: (305) 296-8118
Address: 524 Duval St.
Description: This fun little New York–style bar is not really on Duval; it’s actually situated on Appelrouth Lane, just around the corner from La Trattoria, one of Key West’s best Italian eateries (see the Restaurants chapter). Martinis and their cousins—Gibsons, Manhattans, and cosmopolitans—are the specialty here, and on “Martini Mondays” you can pay only $5 for one. Grab a seat at the bar or in one of the overstuffed easy chairs while you sip your cocktail and listen to live music from some of Key West’s finest musical talent.