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 August 31 – September 6, 2026.

⭐This Week’s Featured Festivals

🌟 This Week’s Highlights

🎟️ Summer Bingo Night

Wednesday, September 2 • 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 2 @ 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 3 @ 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 3 @ 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

🎵 Live Music & Entertainment

Monday, August 31

• Wynn Taylor @ Rams Head Southernmost — 11AM–2 PM
• A Pirate Looks Back: Jimmy Buffett Tribute Show @ Comedy Key West — 12:30 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 1

• Barrett Thomas @ Rams Head Southernmost — 11AM–2 PM
• John Dion @ The Gardens Hotel — 5–7 PM
• Glow Hours @ Hugh’s View atop Studios of Key West— 6–8 PM
• Screaming Broccolli @ Sloppy Joe’s — 10 PM

Wednesday, September 2

• Rick Fusco @ 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
• John Frinzi & Aaron Scherz @ Key West Theater — 7 PM
• Ukulele Night @ Green Parrot— 8 PM
• Graffiti @ Sloppy Joe’s — 10 PM

Thursday, September 3

• Robert Douglas @ Rams Head Southernmost — 11 AM–2 PM
• A Pirate Looks Back: Jimmy Buffett Tribute Show @ Comedy Key West — 12:30 PM
• John Frinzi & Aaron Scherz @ Key West Theater — 7 PM
• Keep It Going: After Party with Nadirah Shakoor @ Margaritaville— 9 PM
• Graffiti @ Sloppy Joe’s — 10 PM

Friday, September 4

• Andy Westcott @ Rams Head Southernmost — 11 AM–2 PM
• Key West’s Favorite Son City Proclamation @ Shrimp Boat Sound— 11 AM–11:30 AM
• A Pirate Looks Back: Jimmy Buffett Tribute Show @ Comedy Key West — 12:30 PM
• Happy Hour All Day @ The Roost — 12–6 PM
• Duval Street Party ft. Landshark Band @ 200 Block of Duval— 5:30–9 PM
• Shastina @ General Horseplay — 7 PM
• Graffiti @ Sloppy Joe’s — 10 PM

Saturday, September 5

• Just a Few Friends: Parrots & Margaritas 5k Run/Walk Party @ Key West Emporium — 8 AM–10 AM
• Through the Lens: Early Buffett Concert Photography Exhibit @ The Pier House — 8 AM–8 PM
• Barrett Thomas@ Rams Head Southernmost — 10:30 AM–1:30 PM
• Screening of Occupational Hazard, The First Coral Reefers @ Key West Theater — 2 PM
• Paul Warthen @ The Gardens Hotel — 5–7 PM
• The Wheeland Brothers @ Sunset Pier— 6:30-9:30 PM
• Keep It Going After Party @ Key West Emporium — 9 PM–Midnight
• Graffiti @ Sloppy Joe’s — 10 PM

Sunday, September 6

• Marjory Lee @ Rams Head Southernmost — 11 AM–2 PM
• Just a Few Friends: Roger Bartlett @ Key West Emporium — 1 PM–3 PM
• John Dion @ The Gardens Hotel — 5–7 PM
• Second Line Memorial Walking Parade @ 100 Duval St — 5–6 PM
• Cayman And The Mango Men: A Buffett Tribute @ Green Parrot — 5:30–7 PM
• Party in the Park: Tribute to Bubba @ Truman Waterfront — 6–10 PM
• Key West Artisan Market at the Party @ Truman Waterfront — 6–10 PM
• Karaoke Night @ General Horseplay — 8 PM
• Graffiti @ 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 & Wed 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

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Bethany Smith-Martin

OurKeyWest Concierge & Vacation Planner at OurKeyWest

I came to Key West New Year's Eve, 1996 to be with my college sweetie who is from Key West. We have made a life of all things Key West. 🏝️

Latest posts by Bethany Smith-Martin (see all)

• This Week in Key West: August 31 – September 6, 2026 - August 31, 2026
• This Week in Key West: August 24 – August 30, 2026 - August 25, 2026
• This Week in Key West: August 17 – August 23, 2026 - August 17, 2026