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Key West Labor Day Events & Activity Guide 2025

key west labor day activity guide

Author: Nathan Knight

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

  • Dates: August 29 – September 1, 2025

  • Details: A Jimmy Buffett-style celebration with live music, beach parties, bar crawls, and charity events.

  • Address: Main stage at Smokin’ Tuna – 211 Duval St, Key West, FL 33040

  • Website: More Info

 

Key West BrewFest 2025

  • Dates: August 28 – September 1, 2025

  • Details: 150+ craft beers, pool parties, food pairings, and nightly tasting events.

  • Address: Southernmost Beach Resort – 1319 Duval St, Key West, FL 33040

  • Website: More Info

 

Parrots & Margaritas 5K + Flip-Flop Mile

  • Date: August 30, 2025

  • Details: Casual 5K run with margaritas, music, and a flip-flop-friendly mile walk.

  • Start Location: Southernmost Beach Café – 1405 Duval St, Key West, FL 33040

  • Website: More Info

 

Labor Day Sunset Cruise Celebrations (Live Music, Food & Drinks)

  • Dates: August 30, 31 & September 1, 2025

  • 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.

  • Departure Location: 201 William St, Key West, FL 33040

  • Sunset Cruise Celebrations: Labor Day Sunset Sail, Labor Day Dinner Cruise

 

Labor Day Weekend Sandbar Celebration

happy hour sandbar charter key west

happy hour sandbar charter key west

 

Labor Day Insider Tip


 

Next Key West Tip: Happy Hour At The Sandbar In Key West

happy hour sandbar charter in key west best thing to do

  • Posted in:
Happy Hour Sandbar Charter With Sunset Cruise
  • Happy Hour!
From $149.95 $129.95

Join us for Happy Hour at the sandbar! The sand-bar is open. This tour also includes a trip to the dolphin playground. Enjoy unlimited beer, mimosas, wine & champagne while you soak up the sun or explore. After the sandbar we will cruise through the Florida Marine Sanctuary for a sunset cruise you won’t forget!

Kids go free!