Holiday events in Key West

Check out happening holiday events all around Key West, FL

Second Line Memorial Walking Parade

 Sun, 31 Aug at 05:00 pm 100 Duval St, Key West, FL 33040-6506, United States

2025 Fantasy Fest Parade Viewing Party @ First Flight

 Sat, 25 Oct at 06:00 pm First Flight Island Restaurant & Brewery USD 177 to 212

Back to the Island Beach Party

 Sat, 30 Aug at 11:00 am 801 Duval St, Key West, FL 33040-7405, United States

Puddles Pity Party at Key West Theater

Sun, 28 Sep at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Brews & Bites: A 4-Course Paired Experience

 Fri, 29 Aug at 07:00 pm First Flight Island Restaurant & Brewery USD 97

Fins Up! Pool Party!!

Sat, 30 Aug at 01:00 pm 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States

Captain Morgan's Masquerade March

 Fri, 24 Oct at 05:30 pm Fleming St, Key West, FL 33040, United States

Pencil Thin Mustache Contest

 Mon, 01 Sep at 02:00 pm Pier House Resort & Spa

Key West's Favorite Son City Proclamation

 Fri, 29 Aug at 11:00 am Shrimp Boat Sounds (Jimmy Buffetts Recording Studio)

Wesley House Holiday Village & Bike Ride

 Fri, 05 Dec at 05:00 pm Coffee Butler Amphitheater

Custom House Holiday Concert & Bazaar

 Fri, 12 Dec at 05:00 pm Key West Art & Historical Society

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

 Tue, 21 Oct at 07:00 pm 423 Caroline street, Key West, FL, United States, Florida 33040

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

 Fri, 21 Nov at 09:00 pm The Alamo Key West

LUV2GLOW - VIVID DREAMS - FANTASY FEST 2025 @Rick's Key West

 Wed, 22 Oct at 08:00 pm Rick's Bar USD 36 to 117

Crystal Gayle

 Fri, 21 Nov at 07:00 pm Key West Theater

Great Gatsby NYE 2026

 Wed, 31 Dec at 08:00 pm First Flight Island Restaurant & Brewery USD 269

Sloppy Joe's Slumber Party

 Wed, 22 Oct at 11:00 am Sloppy Joe's

2025 - Friday, Oct. 31 - Jerry Diaz's Sunset Cruise in Key West!

 Fri, 31 Oct at 05:00 pm Sebago Key West

Berkshire Hathaway Parade of Homes Mega Open House Event

 Thu, 23 Oct at 11:00 am 922 Caroline Street, Key West, FL, United States, Florida 33040

Clay Walker in Key West

 Wed, 29 Oct at 07:00 pm Country Cruising

Come Monday Breakfast Special

 Mon, 01 Sep at 08:00 am 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States

Early Bird Clean Up White Street & Truman Ave hosted by Fausto's Food Palace

Fri, 12 Dec at 08:00 am Fausto's Food Palace

Southernmost Turkey Trot 5K

 Thu, 27 Nov at 08:00 am The Southernmost Point Buoy

Midnight MAss Fantasy Fest

 Fri, 24 Oct at 10:00 pm Island House Key West Gay Hotel & Resort

Key West trip with the Barefoot Bay Travelers Club

 Wed, 15 Oct at 07:30 am Fairfield Inn & Suites by Marriott Key West at The Keys Collection

AG at Sloppy Joes Key West Aug 27-Sept 2!

 Wed, 27 Aug at 10:00 pm Sloppy Joe's Bar