Nightlife & Entertainment

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,…

July 29, 2026

Beyond the bars: a complete guide to Key West entertainment, from live theater and the only Keys comedy club to cabaret, concerts,…

July 28, 2026

The full story of Sloppy Joe's Key West: its 1933 origin, the Hemingway connection, the famous 1937 move, live music, the menu,…

July 27, 2026

A complete guide to Key West breweries and craft beer, from The Waterfront to First Flight and Cayo Hueso, with what to…

July 26, 2026

Discover the best Key West rooftop bars for sunset, which ones actually face the water, plus dress codes, hours, and tips for…

July 25, 2026

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…

July 24, 2026

Discover the best Key West sunset cruise for 2026: Schooner Western Union, Hindu, Appledore Star, Sebago, Fury, Danger Charters with current pricing…

June 1, 2026

Discover the best Key West live music venues for 2026: Smokin' Tuna, Green Parrot Soundchecks, Sloppy Joe's, the Songwriters Festival, and weekly…

May 28, 2026

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…

May 13, 2026

Quick takeaways Duval Street is the spine of Key West nightlife, but the best bars are often a block or two off…

April 14, 2026