This Week in Key West: August 3 – August 9, 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 August 3 – August 9, 2026.
🦞 Key West Lobsterfest
August 5–9, 2026
🌟 This Week at a Glance
- 🦞 Lobster Boil & Pool Parties
- 🛍️ Duval Street Fair
- 🧑🌾 Key West Farmers Market
- 🎵 Live Music Every Day
🌟 This Week’s Highlights
🦞 Key West Lobsterfest
August 5–9, 2026
Celebrate the official opening of Florida’s spiny lobster season during five days of island-wide food, live music, and waterfront fun. Key West Lobsterfest features the famous Lobster Boil, Duval Street Fair, pool parties, pub crawl, lobster-inspired dining, and live entertainment throughout Old Town. Whether you’re a seafood lover or simply looking to experience one of Key West’s signature summer festivals, it’s a delicious way to enjoy the island. LobsterFest Events👉 https://keywestlobsterfest.com/
🎟️ Summer Bingo Night
Wednesday, August 5 • 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 3
• 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 4
• Jacin Waple @ Rams Head Southernmost — 11AM–2 PM
• John Dion @ The Gardens Hotel — 5–7 PM
• Jesse James Russell @ Key West EmPOURium — 6–9 PM
• Naked Karate Girls @ Sloppy Joe’s — 10 PM
Wednesday, August 5
• 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
• Naked Karate Girls @ Sloppy Joe’s — 10 PM
Thursday, August 6
• Robert Douglas @ 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
• RockHouse @ Sloppy Joe’s — 10 PM
Friday, August 7
• Andy Westcott @ Rams Head Southernmost — 11 AM–2 PM
• Happy Hour All Day @ The Roost — 12–6 PM
• The Fabulous Spectrelles @ the Karaoke Lounge-Key West EmPOURium — 7–8 PM
• Wichita Jack @ Doc’s on Duval — 6–9 PM
• Shastina @ General Horseplay — 7 PM
• The Newtons @ Key West Empourium — 6–9 PM
• RockHouse @ Sloppy Joe’s — 10 PM
Saturday, August 8
• Aaron Blumer @ Rams Head Southernmost — 10:30 AM–1:30 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
• Zach Lovering @ General Horseplay— 7 PM
• RockHouse @ Sloppy Joe’s — 10 PM
Sunday, August 9
• 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
• RockHouse @ 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 3–6 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?
Submit local events, live music schedules, and community happenings to OurKeyWest.
- This Week in Key West: August 3 – August 9, 2026 - August 4, 2026
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This Week in Key West: August 3 – August 9, 2026
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