Holiday events in Key West

Check out happening holiday events all around Key West, FL

Key West Lighted Boat Parade 🎄

 Sat, 13 Dec at 07:30 pm 631 Greene St, Key West, FL, United States, Florida 33040

Wesley House Holiday Village & Bike Ride

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

Running of the Elves

 Sat, 20 Dec at 06:00 pm Key West

17th Annual Rudolph APSMC 5K

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

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

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

Grand Opening & Lighting Ceremony for the Official Key West Christmas Fun Headquarters

 Fri, 14 Nov at 05:30 pm 1319 Duval St, Key West, FL 33040-3131, United States

Santa Run + Pilates Wellness Event

 Sat, 13 Dec at 08:00 am Blue Flamingo Resort Key West Free

Time to Talk Turkey!

 Sat, 15 Nov at 07:00 pm 291 Front St suite 207, Key West, FL, United States, Florida 33040

Custom House Holiday Concert & Bazaar

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

The Lighting of the "Harbor Walk of Lights"

 Wed, 26 Nov at 05:00 pm Conch Republic Seafood Company

Time to Talk Turkey!

 Sat, 22 Nov at 07:00 pm 291 Front St suite 207, Key West, FL, United States, Florida 33040

Thanksgiving at Four Marlins

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

A Very Tutu Christmas Trolley 2025!

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

Holiday Lights Conch Tour Train

 Fri, 12 Dec at 06:30 pm Sigsbee Community Center

Lower Keys Chamber Holiday Gala and Installation Dinner

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

Sail with Santa 🎅

 Wed, 03 Dec at 04:15 pm 631 Greene St, Key West, FL 33040-6624, United States

Lighting of the Bight

 Wed, 26 Nov at 05:00 pm Key West Historic Seaport

Holiday Lighted Boat Parade

Sun, 14 Dec at 03:00 pm The Perry Hotel & Marina Key West

FRLA Monroe Cheers to the Holidays!

 Tue, 09 Dec at 05:00 pm Opal Key Resort & Marina USD 19 to 25

Watercolor Fundraiser with Tracey DeLellis at Alonzo's Patio Bar

 Mon, 15 Dec at 06:00 pm Alonzo's Patio Bar

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

An Evening Aglow: A Candlelight Christmas with Marjory Lee

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

Keys Choral Arts: Holiday Concert

 Sat, 13 Dec at 07:00 pm Tennessee Williams Theatre

Winterfest

 Thu, 04 Dec at 04:00 pm Sigsbee Community Center

Pet Photos With The Grinch

 Thu, 04 Dec at 04:30 pm 336 Duval St, Key West, FL, United States, Florida 33040

Italian Night at the Movies: Light in the Piazza

 Wed, 03 Dec at 05:30 pm Tropic Cinema

Christmas on the Farm Open House

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

Reef Relief Annual Holiday Train

 Wed, 10 Dec at 06:00 pm 631 Greene St, Key West, FL, United States, Florida 33040

Build-a-Bouquet

 Mon, 24 Nov at 06:00 pm Sigsbee Community Center

Kid's Crafts AT NIGHT: Elf Workshop

 Wed, 10 Dec at 06:00 pm Sigsbee Community Center

Christmas Eve & Christmas Day Lunch & Dinner at Yellowfin

 Wed, 24 Dec at 02:00 pm 5950 Peninsular Avenue, Key West, FL, United States, Florida 33040

Christmas at Matt's Stock Island Kitchen & Bar

 Wed, 24 Dec at 12:30 pm 7001 Shrimp Road, Key West, FL, United States, Florida 33040

Yachtley Crew

 Wed, 18 Feb at 08:00 pm Key West Theater

Holiday Concert at Tennessee Williams Theatre

 Sun, 14 Dec at 04:00 pm Tennessee Williams Theatre

Annual Holiday Ornament Paint Night, with Jess

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

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