Key West Labor Day Events & Activity Guide 2025
Celebrate Labor Day In Key West With These Events & Top Things To Do
Labor Day Weekend (August 29 – September 1, 2025) is one of the best times to visit Key West. The island transforms into a sun-soaked celebration with live music, food festivals, waterfront parties and unforgettable tours. Whether you’re honoring Jimmy Buffett’s legacy at the Just A Few Friends Festival, sipping cold brews at BrewFest or Key West’s Labor Day sunset cruise or sandbar celebration with Sunset Watersports, there’s no shortage of fun. This is your complete guide to Labor Day in Key West.
Top Things To Do In Key West For Labor Day Weekend 2025
Just a Few Friends Festival
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Dates: August 29 – September 1, 2025
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Details: A Jimmy Buffett-style celebration with live music, beach parties, bar crawls, and charity events.
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Address: Main stage at Smokin’ Tuna – 211 Duval St, Key West, FL 33040
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Website: More Info
Key West BrewFest 2025
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Dates: August 28 – September 1, 2025
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Details: 150+ craft beers, pool parties, food pairings, and nightly tasting events.
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Address: Southernmost Beach Resort – 1319 Duval St, Key West, FL 33040
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Website: More Info
Parrots & Margaritas 5K + Flip-Flop Mile
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Date: August 30, 2025
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Details: Casual 5K run with margaritas, music, and a flip-flop-friendly mile walk.
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Start Location: Southernmost Beach Café – 1405 Duval St, Key West, FL 33040
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Website: More Info
Labor Day Sunset Cruise Celebrations (Live Music, Food & Drinks)
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Dates: August 30, 31 & September 1, 2025
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Details: Celebrate Labor Day weekend with a sunset sail featuring a live DJ, unlimited beer, wine, and champagne — all while cruising past the famous Key West sunset.
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Departure Location: 201 William St, Key West, FL 33040
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Sunset Cruise Celebrations: Labor Day Sunset Sail, Labor Day Dinner Cruise
Labor Day Weekend Sandbar Celebration
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Dates: August 29 – September 1, 2025 (Daily trips)
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Details: Cruise to a secluded tropical sandbar, swim, relax and enjoy unlimited drinks in paradise.
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Departure Location: 201 William St, Key West, FL 33040
- Sandbar Tours: Sandbar & Kayak Tour Party, Sandbar & Dolphin Tour Party, Happy Hour Sandbar Tour Party
happy hour sandbar charter key west
Labor Day Insider Tip
- Save tons of money on your restaurant & bar tabs this Labor Day in Key West with the new bar discount program called Party Pass Key West. This program gives you exclusive free drinks and discounts at tons of Key West’s most popular bars and restaurants. More Info
- Check out all of Key West’s top Labor Day activities.
Next Key West Tip: Happy Hour At The Sandbar In Key West
