Holiday events in Key West

Check out happening holiday events all around Key West, FL

2025 Fantasy Fest Parade Viewing Party @ First Flight

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

Crystal Gayle

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

Black Friday Shopping Extravaganza

 Fri, 28 Nov at 10:00 am Truman Waterfront Park

Custom House Holiday Concert & Bazaar

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

Wesley House Holiday Village & Bike Ride

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

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

Key West Lighted Boat Parade

 Sat, 13 Dec at 08:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

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

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

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

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

A Very Tutu Christmas Trolley 2025!

Mon, 15 Dec at 06:30 pm 504 Angela St, Key West, FL, United States, Florida 33040

17th Annual Rudolph APSMC 5K

 Sat, 13 Dec at 07:00 am Southernmost Beach Resort

An Evening Aglow: A Candlelight Christmas with Marjory Lee

 Tue, 16 Dec at 06:30 pm Key West Theatre

Thanksgiving at Four Marlins

 Thu, 27 Nov at 05:30 pm 1435 Simonton St, Key West, FL 33040

Italian Night at the Movies: Light in the Piazza

 Wed, 03 Dec at 05:30 pm Tropic Cinema

Great Gatsby NYE 2026

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

Christmas on the Farm Open House

 Sun, 14 Dec at 01:00 pm Monroe County Sheriff's Office Animal Farm

Lower Keys Chamber Holiday Gala and Installation Dinner

 Wed, 03 Dec at 06:00 pm Tennessee Williams Theatre

Celebrate Thanksgiving at the Key West Cooking Show

 Thu, 27 Nov at 11:00 am 291 Front St suite 207, Key West, FL, United States, Florida 33040

Midnight MAss Fantasy Fest

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

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

Annual Holiday Ornament Paint Night, with Jess

 Wed, 10 Dec at 05:30 pm 22&Co

Clay Walker in Key West

 Wed, 29 Oct at 07:00 pm Country Cruising

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