This Week in Key West: November 9-15, 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 November 9 – 15, 2026.

🌟 This Week’s Highlights

🌅Glow Hours on Hugh’s View

Tuesdays @ Studios of Key West— 5-7 pm
Glow Hours are your invitation to slow down, head upstairs, and take in Key West from one of the best viewpoints in town. Join us on Hugh’s View for drinks, conversation, and spectacular rooftop sunsets overlooking the island. Whether you’re catching up with friends or simply soaking in the view, it’s an easygoing way to spend an evening at The Studios.

👢Line Dancing Class

Wednesday, November 11 @ 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, November 12 @ 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/

🎨Paint & Sip

Friday, November 13 @ Doc’s on Duval — 6–8 PM
Join Ocean Side Art for a Paint & Sip night at Doc’s Downstairs! Tickets are $20-$30 per painter and include all necessary supplies and instruction.

🎤 Karaoke

Nightly @ Key West Empourium — 8-12:30 AM
Unleash your inner pop star every night of the week at The Key West EmPOURium’s Karaoke Lounge!
Bring your friends and family, grab a drink, and belt your heart out to any one of thousands of songs, spun up by our in-house DJ!
This is your chance to show the world what you’re made of…What song will you choose?

🌴 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, November 9

• Wynn Taylor @ Rams Head Southernmost— 11AM–2 PM
• Mary Spear @ The Gardens Hotel— 5–7 PM
• Colton Gleghorn @ Key West EmPOURium— 6–9 PM
• Martinis w/ Melodic Beats @ General Horseplay— 9 PM
• Rock House @ Sloppy Joe’s— 10 PM

Tuesday, November 10

• Lee Sharpe @ Rams Head Southernmost— 11AM–2 PM
• John Dion @ The Gardens Hotel— 5–7 PM
• Nina Newton @ Key West EmPOURium— 6–9 PM
• Bill Steely @ Doc’s on Duval— 6–9 PM
• Glow Hours @ Hugh’s View atop Studios of Key West— 5–7 PM
• See You Next Tuesday @ General Horseplay— 8 PM
• Rock House @ Sloppy Joe’s— 10 PM

Wednesday, November 11

• Jacin Waple @ Rams Head Southernmost— 11 AM–2 PM
• A Pirate Looks Back: A Jimmy Buffett Tribute Show @ Comedy Key West— 12:30 PM
• Kenny Albert Duo @ The Gardens Hotel— 5–7 PM
• Witchita Jack @ Doc’s on Duval— 6–9 PM
• Line Dancing @ Key West EmPOURium— 6:30–8:30 PM
• Jerico@ General Horseplay— 9 PM
• Screaming Broccoli @ Sloppy Joe’s— 10 PM

Thursday, November 12

• Ross Brown @ Rams Head Southernmost— 11 AM–2 PM
• Craig Hauser @ The Gardens Hotel— 5–7 PM
• Mac Calhoun @ Key West EmPOURium— 6–9 PM
• Christopher Maloney @ Doc’s on Duval— 6–9 PM
• Astro Yeti @ General Horseplay— 9 PM
• Screaming Broccoli @ Sloppy Joe’s— 10 PM

Friday, November 13

• Andy Westcott @ Rams Head Southernmost— 11 AM–2 PM
• Happy Hour All Day @ The Roost— 12–6 PM
• Bill Steely @ Doc’s on Duval— 1–4 PM
• Jon Hollywood @ Key West EmPOURium— 8–11 PM
• Bill Steely @ Doc’s on Duval— 6–9 PM
• Shastina @ General Horseplay— 7 PM
• The Fabulous Spectrelles @ the Karaoke Lounge @ Key West Empourium— 7-8 PM
• Killer Prom @ Key West Theater—7 PM
• Screaming Broccoli @ Sloppy Joe’s— 10 PM

Saturday, November 14

• Aaron Blumer @ Rams Head Southernmost— 10:30 AM–1:30 PM
• Zach Lovering @ General Horseplay— 7 PM
• Jesse James Russell @ Doc’s on Duval— 6–9 PM
• A Tribute to the Song of Pete & Wayne, w/ Pete Jarvis, Larry Strickland, Ray Fogg & Friends @ Key West Theater—8 PM
• CW Colt @ Key West EmPOURium— 8–11 PM
• Screaming Broccoli @ Sloppy Joe’s— 10 PM

Sunday, November 15

• Marjorie Lee @ Rams Head Southernmost— 11 AM–2 PM
• The Juliano Brothers @ Green Parrot Bar— 1 & 3 PM
• Jazz in the Gardens with Jody Rae, Larry Smith, & Mark Rose @ The Gardens Hotel— 5–7:00 PM
• Reggae Lou & The Kind Budz @ Key West EmPOURium— 6–9 PM
• A Tribute ti the Song of Pete & Wayne, w/ Pete Jarvis, Larry Strickland, Ray Fogg & Friends @ Key West Theater—8 PM
• Screaming Broccoli @ Sloppy Joe’s— 10 PM