This Week in Key West: September 21-27, 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 September 21-27, 2026.

🌟 This Week’s Highlights

🎟️ Summer Bingo Night

Wednesday, September 23 • 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. More info: https://thekeywesttheater.com/

👢Line Dancing Class

Wednesday, September 23 @ Key West EmPOURium — 6:30–8:30 PM
Dust off yer boots and learn to line dance. FREE.
More info: https://www.empouriumkeywest.com/

🤓Jackpot Trivia

Thursday, September 24 @ 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.
More info: https://www.empouriumkeywest.com/

🧑‍🌾Key West Farmers Market

Thursday, September 24 @ Truman Waterfront — 1–6 PM
Discover the vibrant Florida Keys Farmers Market, where fresh local flavors, handmade treasures, and island charm come together in a lively open-air setting. Browse seasonal produce, unique artisan goods, delicious food, and locally crafted finds while enjoying live music and the welcoming spirit of the Keys.
More info: https://keysartisanmarket.com/farmersmarket.htm

🌴 Our Concierge Pick

⛵ Schooner 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

Planning a future trip to Key West?

Browse festivals, concerts, races, holiday celebrations, and special events happening throughout the year.

View our complete 2026 Key West Events Calendar →

🎵 Live Music & Entertainment

Monday, September 21

• Wynn Taylor @ Rams Head Southernmost— 11AM–2 PM
• Mary Spear @ The Gardens Hotel— 5–7 PM
• Charity Bingo @ Green Parrot Bar— 7–9 PM
• Martinis w/ Melodic Beats @ General Horseplay— 9 PM

Tuesday, September 22

• Zack Seemiller @ Rams Head Southernmost— 11AM–2 PM
• John Dion @ The Gardens Hotel— 5–7 PM
• The Happy Dog @ Green Parrot Bar— 5:30 PM
• Glow Hours @ Hugh’s View atop Studios of Key West— 6–8 PM
• Dear Zoe @ Sloppy Joe’s— 10 PM

Wednesday, September 23

• Rick Fusco @ Rams Head Southernmost— 11 AM–2 PM
• Kenny Albert @ The Gardens Hotel— 5–7 PM
• Line Dancing @ Key West EmPOURium— 6:30–8:30 PM
• Mac Calhoun @ Key West EmPOURium— 6–9 PM
• Crownz @ Sloppy Joe’s— 10 PM

Thursday, September 24

• Robert Douglas @ Rams Head Southernmost— 11 AM–2 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• Tony Baltimore & The Wilde Awake @ Green Parrot Bar— 5:30 PM
• Mac Calhoun & Colton Cleghorn @ Key West Empourium— 6–9 PM
• Adam Luffkid @ General Horseplay— 9 PM
• Crownz@ Sloppy Joe’s— 10 PM

Friday, September 25

• Andy Westcott @ Rams Head Southernmost— 11 AM–2 PM
• Happy Hour All Day @ The Roost— 12–6 PM
• Jon Hollywood @ Key West Empourium— 6–9 PM
• The Fabulous Spectrelles @ Key West Empourium— 7–8 PM
• Shastina @ General Horseplay— 7 PM
• Crownz @ Sloppy Joe’s— 10 PM

Saturday, September 26

• Barrett Thomas @ Rams Head Southernmost— 10:30 AM–1:30 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• Nick Norman: Live Recoding in the Listening Room @ Key West Theater—7 PM
• Zach Lovering @ General Horseplay— 7 PM
• Toko Irie @ Key West Emporium— 6–9 PM
• Crownz @ Sloppy Joe’s— 10 PM

Sunday, September 27

• Marjory Lee @ Rams Head Southernmost— 11 AM–2 PM
• Cayman & Company @ Green Parrot Bar— 1 & 3 PM
• John Dion @ The Gardens Hotel— 5–7:30 PM
• Karaoke Night @ General Horseplay— 8 PM
• Crownz @ Sloppy Joe’s— 10 PM