Key West Guide - Nightlife

Key West After Dark

Since Sloppy Joe's occupied the quarters now known as Captain Tony's, the bars of Key West have offered colorful places to spend a tropical evening. Although many of the newer hotels have their own atmospheric bars and lounges, the Old Town bars are still popular places to drink and meet people. Here are a few of the best:

Captain Tony's Saloon
428 Green Street (305) 294-1838
A truly historic building, Capt. Tony's is the original location of the famed Sloppy Joe's. The bar was named after Capt. Tony Tarracino, a friend of Earnest Hemingway who once owned the place. The walls of the saloon are covered with underwear. Entertainment nightly.

Sloppy Joe's Bar
201 Duval St. (305) 294-5717
The operation moved to this location in 1937. Hemingway is said to have written some of his works in a back room of the bar, and certainly was a daily visitor. The walls have Hemingway photos and memorabilia, and the whole place has a nostalgic atmosphere. The bar offers live entertainment daily from noon (until 2 a.m.) except Mondays at 9 p.m. when the "Moon Dance" contest is held. There's a gift shop with Sloppy Joe's souvenirs.

Turtle Kraals
1 Land's End Village (305) 294-2640
This is a restaurant with a large lounge attached, serving up a variety of Microbrews, imported beer, and margaritas. There's a happy hour, plus entertainment nightly in this open-air waterfront bar.

Pier House Resort
1 Duval St. (305) 296-4600
The Pier House has been a fixture in Old Town Key West for a long time. There's a piano bar in the Wine Gallery, as well as Schooner Wharf, an indoor/outdoor lounge. Live music is featured Thursdays through Saturdays.

C.C. Ryder's Piano Bar
611 Duval St. (305) 296-6625
The famous pianist play at this lounge, reminiscent of New Orleans. The music begins at 5 p.m. on Fridays and Saturdays, and at 8 p.m. Sundays and Thursdays. It's closed Monday through Wednesday.

Green Parrot Bar
601 Whitehead St. (305) 294-6133
Located in a building dating from 1890, the Green Parrot is a longtime hangout for locals. Bands play on weekends, and the bar has video games, bollards, darts, and a jukebox.

Flagler's Restaurant and Lounge
1500 Reynold's Street (305) 296-3535
This restaurant with lounge is found inside Marriott's Casa Marina Resort. The lounge features jazz and pop music, with dancing.

Gay Nightspots

While all Key West nightspots welcome all visitors, the following places cater to the gay crowd.

Atlantic Shores Resort
510 South St. (305) 296-2491
With an art deco look, Atlantic Shores is Miami Beach brought to the Caribbean. The weekly tea dances here are famous. They're held on Sunday nights with a disc jockey providing poolside music, and cocktails are served. It's the headquarters for WomenFest, the annual event, held this year from September 5 to 10.

801 Duval St. (305) 294-4737
This popular bar features billiards.

1029 Truman Avenue (305) 296-0333
Shows are held from 11 p.m. to 2 a.m. nightly, in this male strip club.

Bourbon Street
724 Duval St. (305) 296-1992
The place is known for its live music, comedy acts, and drag shows. Disc jockey music nightly, with a long long happy hour daily from noon to 8 p.m. On Friday -- the most popular night -- bartenders dress in drag.


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