This Week in Key West: November 2 - 8, 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 2 – 8, 2026.

⭐This Week’s Featured Event

🚤Race World Offshore World Championship

November 1 – 8th @ Truman Waterfront Park
High-speed offshore racing returns to Key West with a full week of competition, festivities, and waterfront excitement.

🌟 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 4 @ 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 5 @ 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 6 @ 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.

🌴 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 2

• 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
• Naked Karate Girls @ Sloppy Joe’s— 10 PM

Tuesday, November 3

• 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
• Honky Tonk Tuesday @ General Horseplay— 9 PM
• Naked Karate Girls @ Sloppy Joe’s— 10 PM

Wednesday, November 4

• 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 @ The Gardens Hotel— 5–7 PM
• Zach Lovering & Adam Luffkin @ General Horseplay— 5:30 PM
• Witchita Jack @ Doc’s on Duval— 6–9 PM
• Line Dancing @ Key West EmPOURium— 6:30–8:30 PM
• Rock House @ Sloppy Joe’s— 10 PM

Thursday, November 5

• Ross Brown @ Rams Head Southernmost— 11 AM–2 PM
• Paul Warthen @ The Gardens Hotel— 5–7 PM
• Mac Calhoun @ Key West EmPOURium— 6–9 PM
• Christopher Maloney @ Doc’s on Duval— 6–9 PM
• Funky Lamp Shades @ General Horseplay— 9 PM
• Rock House @ Sloppy Joe’s— 10 PM

Friday, November 6

• 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
• Marshall Morlock @ Key West EmPOURium— 8–11 PM
• Jon Hollywood @ 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
• Rock House @ Sloppy Joe’s— 10 PM

Saturday, November 7

• Aaron Blumer @ Rams Head Southernmost— 10:30 AM–1:30 PM
• Zach Lovering @ General Horseplay— 7 PM
• Toko Irie @ Doc’s on Duval— 6–9 PM
• Killer Prom @ Key West Theater—7 PM
• Marshall Morlock @ Key West EmPOURium— 8–11 PM
• Ocean Blue @ Key West Theater—8 PM
• Rock House@ Sloppy Joe’s— 10 PM

Sunday, November 8

• Marjorie Lee @ Rams Head Southernmost— 11 AM–2 PM
• The Juliano Brothers @ Green Parrot Bar— 1 & 3 PM
• Scott Marischen @ The Gardens Hotel— 5–7:30 PM
• Reggae Lou & The Kind Budz @ Key West EmPOURium— 6–9 PM
• Killer Prom @ Key West Theater—7 PM
• Bruce Cockburn & Livingston Taylor @ Key West Theater—8 PM
• Tera Lynn Trio @ General Horseplay— 8 PM
• Rock House @ Sloppy Joe’s— 10 PM