This Week in Key West: July 13 – July 19, 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 13 – July 19, 2026.
🎟️ Summer Bingo Night
🧑🌾 Key West Farmers Market
🤓 Jackpot Trivia
🌅 Sunset Sail in the Key West Harbor
🌟 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 15 • 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.
🧑🌾Farmer’s Market
Thursday, July 16 • Truman Waterfront Park • 1-6 pm
🤓Jackpot Trivia
Thursday, July 16 @ 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.
🌴 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 13
• Tony Roberts @ Rams Head Southernmost — 6–9 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 14
• 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
• Crownz @ Sloppy Joe’s — 10 PM
Wednesday, July 15
• 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
• King Pin @ Sloppy Joe’s — 10 PM
Thursday, July 16
• 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
• Connor McLaren @ General Horseplay— 9 PM
• King Pin @ Sloppy Joe’s — 10 PM
Friday, July 17
• Andy Westcott @ Rams Head Southernmost — 11 AM–2 PM
• Happy Hour All Day @ The Roost — 12–6 PM
• Fish Out of Water @ Key West EmPOURium — 5–8 PM
• The Fabulous Spectrelles @ the Karaoke Lounge-Key West EmPOURium — 6–9 PM
• Wichita Jack @ Doc’s on Duval — 6–9 PM
• Shastina @ General Horseplay — 7 PM
• King Pin @ Sloppy Joe’s — 10 PM
Saturday, July 18
• Aaron Blumer @ Rams Head Southernmost — 10:30 AM–1:30 PM
• Jazz in the Garden @ The Gardens Hotel — 5–7 PM
• Fish Out of Water @ The EmPOURium — 5–8 PM
• Jesse James Russell @ Doc’s on Duval — 6–9 PM
• Summertime Stories: Original Son Session with Meghan Barter @ Key West Theater — 7 PM
• Zach Lovering @ General Horseplay— 7 PM
• King Pin @ Sloppy Joe’s — 10 PM
Sunday, July 19
• Marjorie Lee @ Rams Head Southernmost — 11 AM–2 PM
• Pierce August @ Mac’s Place —4:30 PM–7:30 PM
• Jazz in the Garden @ The Gardens Hotel — 5–7 PM
• Fish Out of Water @ Key West EmPOURium — 5–8 PM
• King Pin @ 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 13 – July 19, 2026 - July 13, 2026
- This Week in Key West: July 6 – July 12, 2026 - July 7, 2026
- This Week in Key West: June 29-July 5, 2026 - June 29, 2026
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