Key West Comedy Shows, Theater, and Performing Arts
Beyond the bars: a complete guide to Key West entertainment, from live theater and the only Keys comedy club to cabaret, concerts, and free sunset performers.
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Nightlife & Entertainment
Key West after dark: Duval Street bars, live music, the Mallory Square sunset celebration, drag shows and where locals drink away from the crowds.
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Key West Drag Shows and LGBTQ Nightlife Guide
Your guide to Key West drag shows and LGBTQ nightlife: the 801 Girls, Aqua, La Te Da, show times, free vs ticketed, tipping etiquette, and the best gay bars.
Sloppy Joe’s Key West: History, Events, and Visitor Guide
The full story of Sloppy Joe's Key West: its 1933 origin, the Hemingway connection, the famous 1937 move, live music, the menu, and tips for visiting today.
Key West Brewery and Craft Beer Guide
A complete guide to Key West breweries and craft beer, from The Waterfront to First Flight and Cayo Hueso, with what to order, tours, and a tasting-flight plan.
Best Rooftop Bars in Key West with Sunset Views
Discover the best Key West rooftop bars for sunset, which ones actually face the water, plus dress codes, hours, and tips for the perfect golden-hour drink.
The Duval Crawl: How to Bar Hop Key West Like a Local
Plan the perfect Key West pub crawl with our self-guided Duval Street route, must-visit bars, go-cup rules, guided tour picks, and local money-saving tips.
Key West Sunset Cruise: Best Schooners & Catamarans (2026)
Discover the best Key West sunset cruise for 2026: Schooner Western Union, Hindu, Appledore Star, Sebago, Fury, Danger Charters with current pricing and vibe matrix.
Key West Live Music: Best Venues & Weekly Schedules (2026)
Discover the best Key West live music venues for 2026: Smokin' Tuna, Green Parrot Soundchecks, Sloppy Joe's, the Songwriters Festival, and weekly schedules.
Duval Street Bars Key West: Complete 2026 Guide & Bar Crawl
Tour the Duval Street bars Key West with this 2026 guide: Sloppy Joe's, Captain Tony's, Hog's Breath, drag shows, dive bars, live music, and a recommended bar crawl.
Key West Nightlife Guide: Bars, Clubs, and Live Music
Quick takeaways Duval Street is the spine of Key West nightlife, but the best bars are often a block or two off it. Bars serve until 4 a.m.…