This Week in Key West: July 20 – July 26, 2026
Looking for things to do in Key West this week? Discover live music, local events, art walks, happy hours, nightlife, and island happenings taking place July 20 – July 26, 2026.
🌟 This Week at a Glance
- 🐾 Sloppy Joe’s Hemingway® Look-Alike Contest
- 🎣 Key West Marlin Tournament
- 🎟️ Summer Bingo Night
- 🧑🌾 Key West Farmers Market
- 🎵 Live Music Every Day
🎉 This Week’s Festival
🐾 Sloppy Joe’s 45th Annual Hemingway® Look-Alike Contest
July 22–26, 2026
One of Key West’s most beloved annual traditions returns during Hemingway Days. More than 150 contestants from around the world compete at Sloppy Joe’s Bar for the coveted Hemingway Look-Alike title while enjoying five days of live entertainment, literary events, street celebrations, and plenty of island fun.
💡 Local Tip: Arrive early for the preliminary rounds—they fill up quickly and are one of the most entertaining events of the summer.
👉 Learn More About Hemingway Days →
🌟 This Week’s Highlights
🌅 Glow Hours at Hugh’s View
Tuesdays every week • The Studios of Key West Rooftop
Take in panoramic sunset views while enjoying drinks, art, and one of Key West’s newest rooftop experiences above The Studios of Key West.
🎟️ Summer Bingo Night
Wednesday, July 22 • Key West Theater • Free Entry • 6 pm
A fun, free community favorite with prizes, drinks, and plenty of laughs. Doors open at 6:00 PM and bingo begins at 7:00 PM.
🤓Jackpot Trivia
Thursday, July 22 @ Key West EmPOURium — 6–7:30 PM
Bring your besties and your brain power for a fun-filled night of trivia with host, Bill Hoebee. Free to attend. Win prizes! Sponsored by Pilar Rum and Bombara Vodka.
🎣 Key West Marlin Tournament
July 22–25, 2026
Celebrating its 45th year, the Key West Marlin Tournament returns during Hemingway Days with four days of world-class offshore fishing, exciting dockside events, and more than $50,000 in cash prizes. Anglers from around the world compete in the legendary waters off Key West while spectators can enjoy the weigh-ins, nightly festivities, and island atmosphere.
👉 Learn more : https://keywestmarlin.com
🌴 Our Concierge Pick
⛵ Sunset Sail
Nightly • Key West Harbor
Watching the sunset from the water is one of the most memorable experiences in Key West. Whether you prefer a classic schooner, a spacious catamaran, or a lively cruise with live music and cocktails, there’s a sunset sail for every style.
💡 Concierge Tip: Sunset sails are one of our most popular recommendations and often sell out—especially on weekends. Reserve early for the best availability.
👉 Book Your Sunset Sail: Key West Sunset Sail Options
🎵 Live Music & Entertainment
Monday, July 20
• Nick Norman @ Rams Head Southernmost — 11AM–2 PM
• Mary Spear @ The Gardens Hotel — 5–7 PM
• Colton Gleghorn @ Key West EmPOURium — 6–9 PM
• Charity Bingo @ Green Parrot Bar — 7–9 PM
• Martinis w/ Melodic Beats @ General Horseplay — 9 PM
Tuesday, July 21
• John Dion @ The Gardens Hotel — 5–7 PM
• Zack Seemiller @ Rams Head Southernmost — 6–9 PM
• Jesse James Russell @ Key West EmPOURium — 6–9 PM
• Stop Making Sense film screening @ General Horseplay— 7 PM
• King Pin @ Sloppy Joe’s — 10 PM
Wednesday, July 22
• Sharese @ Rams Head Southernmost — 11 AM–2 PM
• Kenny Albert @ The Gardens Hotel — 5–7 PM
• A Pirate Looks Back: Jimmy Buffett Tribute Show @ Comedy Key West — 12:30 PM
• Line Dancing @ Key West EmPOURium — 6:30–8:30 PM
• Actual Bank Robbers @ Sloppy Joe’s — 10 PM
Thursday, July 23
• Robert Douglas @ Rams Head Southernmost — 11 AM–2 PM
• Mac Calhoun @ Key West EmPOURium — 6–9 PM
• Chris Maloney @ Doc’s on Duval — 6–9 PM
• Victoria Leigh @ General Horseplay— 9 PM
• Actual Bank Robbers @ Sloppy Joe’s — 10 PM
Friday, July 24
• Andy Westcott @ Rams Head Southernmost — 11 AM–2 PM
• Happy Hour All Day @ The Roost — 12–6 PM
• The Fabulous Spectrelles @ the Karaoke Lounge-Key West EmPOURium — 7–8 PM
• Wichita Jack @ Doc’s on Duval — 6–9 PM
• Conner McLaren @ General Horseplay — 7 PM
• Actual Bank Robbers @ Sloppy Joe’s — 10 PM
Saturday, July 25
• Aaron Blumer @ Rams Head Southernmost — 10:30 AM–1:30 PM
• Paul Warthen @ The Gardens Hotel — 5–7 PM
• Toko Irie @ The EmPOURium — 6–9 PM
• Jesse James Russell @ Doc’s on Duval — 6–9 PM
• Zach Lovering @ General Horseplay— 7 PM
• Actual Bank Robbers @ Sloppy Joe’s — 10 PM
Sunday, July 26
• Marjorie Lee @ Rams Head Southernmost — 11 AM–2 PM
• Horseplay Punch Classic @ General Horseplay 2C Back Bar— 4 PM
• Pierce August @ Mac’s Place —4:30 PM–7:30 PM
• Jazz in the Garden with John Dion @ The Gardens Hotel — 5–7 PM
• Toko Irie & New Beginnings @ Key West EmPOURium — 6–9 PM
• Actual Bank Robbers @ Sloppy Joe’s — 10 PM
🍹 Happy Hour Picks
- Doc’s on Duval — Daily, 4–6 PM
- Dragon & Rooster — Daily, 3–5 PM
- General Horseplay — Sun 12–3 PM · Tues 3–6 PM
- Half Shell Raw Bar — Daily, 4:30–6:30 PM
- Kaya Island Eats — Daily, 4–6 PM
- Mary Ellen’s Bar — Mon, Tues, Wed, Fri 3:30–5:30 PM · Thurs 3:30–5 PM
- The Roost — Daily, 4–6 PM
- Rams Head Southernmost Cafe — Daily, 4–6 PM
Looking for even more events throughout the year? Browse the complete Key West Events Calendar →
Planning a Future Trip?
Looking ahead? Browse our complete annual calendar of festivals, concerts, races, holiday celebrations, and special events.
👉View the Key West Events Calendar
Have an event to add?
Submit local events, live music schedules, and community happenings to OurKeyWest.
- This Week in Key West: July 20 – July 26, 2026 - July 21, 2026
- This Week in Key West: July 13 – July 19, 2026 - July 13, 2026
- This Week in Key West: July 6 – July 12, 2026 - July 7, 2026
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