🥃 Key West Rum Fest

August 10–16, 2026

🌟 This Week at a Glance

🌟 This Week’s Highlights

🥃 Key West Rum Fest

August 12–16

A five-day island celebration featuring world-class rum tastings, live music, cocktail events, unique culinary experiences, and the Grand Tasting with 40+ rum vendors.
Schedule here: https://rumfestkeywest.com

🎟️ Summer Bingo Night

Wednesday, August 12 • 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/

🤓Jackpot Trivia

Thursday, August 6 @ 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/

🌴 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 10

• Wynn Taylor @ Rams Head Southernmost — 11AM–2 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, August 11

• Jacin Waple @ 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
• Jesse James Russell @ Key West EmPOURium — 6–9 PM
• Movie Screening of ‘Cocktail’ @ General Horseplay— 7 PM
• RockHouse @ Sloppy Joe’s — 10 PM

Wednesday, August 12

• 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
• Topher Brown and the Family Business @ Sloppy Joe’s — 10 PM

Thursday, August 13

• Tony Roberts @ Rams Head Southernmost — 11 AM–2 PM
• Lobster Boil @ Fogarty’s — 5–8 PM
• Mac Calhoun @ Key West EmPOURium — 6–9 PM
• Chris Maloney @ Doc’s on Duval — 6–9 PM
• the Why Nots @ General Horseplay— 9 PM
• Topher Brown and the Family Business @ Sloppy Joe’s — 10 PM

Friday, August 14

• Andy Westcott @ Rams Head Southernmost — 11 AM–2 PM
• Happy Hour All Day @ The Roost — 12–6 PM
• Wichita Jack @ Doc’s on Duval — 6–9 PM
• Shastina @ General Horseplay — 7 PM
• The Newtons @ Key West Empourium — 6–9 PM
• The Fabulous Spectrelles @ the Karaoke Lounge-Key West EmPOURium — 7–8 PM
• Cliff Cody & Sharese – Rum Fest 2026 @ Key West Theater — 8 PM
• Topher Brown and the Family Business @ Sloppy Joe’s — 10 PM

Saturday, August 15

• Aaron Blumer @ Rams Head Southernmost — 10:30 AM–1:30 PM
• Grand Tasting with Key West Rum Fest @ Key West Theater — 2:30–5:30 PM
• Paul Warthen @ The Gardens Hotel — 5–7 PM
• Toko Irie @ The EmPOURium — 6–9 PM
• Jesse James Russell @ Doc’s on Duval — 6–9 PM
• Barrett Thomas @ General Horseplay— 7 PM
• Jesse Rice w/ Dawson Wright & Berkley Lindley – Rum Fest 2026 @ Key West Theater — 8 PM
• Topher Brown and the Family Business @ Sloppy Joe’s — 10 PM

Sunday, August 16

• Robert Douglas @ Rams Head Southernmost — 11 AM–2 PM
• Pierce August @ Mac’s Place —4:30 PM–7:30 PM
• Jazz in the Garden with John Dion @ The Gardens Hotel — 5–7 PM
• Topher Brown and the Family Business @ 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 · 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

Have an event to add?
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• About
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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 10 – August 16, 2026 - August 10, 2026
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