Key West Holiday Events

Holiday events Happening Next in Key West, FL

Key West Lighted Boat Parade 🎄

 631 Greene St, Key West, FL, United States, Florida 33040 13 Dec 2025
PARADES

Wesley House Holiday Village & Bike Ride

 Coffee Butler Amphitheater 5 Dec 2025
CYCLING

Keys Choral Arts: Holiday Concert

 Tennessee Williams Theatre 13 Dec 2025
CONCERTS

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

 The Alamo Key West 21 Nov 2025
PARTIES

Custom House Holiday Concert & Bazaar

 Key West Art & Historical Society 12 Dec 2025
MUSIC

Time to Talk Turkey!

 291 Front St suite 207, Key West, FL, United States, Florida 33040 15 Nov 2025
WORKSHOPS

Time to Talk Turkey!

 291 Front St suite 207, Key West, FL, United States, Florida 33040 22 Nov 2025
WORKSHOPS

Italian Night at the Movies: Light in the Piazza

 Tropic Cinema 3 Dec 2025
ENTERTAINMENT

Thanksgiving at Four Marlins

 1435 Simonton St, Key West, FL 33040 27 Nov 2025
THANKSGIVING

Running of the Elves

 Key West 20 Dec 2025
SPORTS

Celebrate Thanksgiving at the Key West Cooking Show

 291 Front St suite 207, Key West, FL, United States, Florida 33040 27 Nov 2025
THANKSGIVING

Yachtley Crew

 Key West Theater 18 Feb 2026
MUSIC

An Evening Aglow: A Candlelight Christmas with Marjory Lee

 Key West Theatre 16 Dec 2025
CHRISTMAS

Holiday Concert at Tennessee Williams Theatre

 Tennessee Williams Theatre 14 Dec 2025
ART

Lighting of the Bight

 Key West Historic Seaport 26 Nov 2025
HOLIDAY

Reef Relief Annual Holiday Train

 631 Greene St, Key West, FL, United States, Florida 33040 10 Dec 2025
HOLIDAY

A Very Tutu Christmas Trolley 2025!

504 Angela St, Key West, FL, United States, Florida 33040 15 Dec 2025
CHRISTMAS

Christmas on the Farm Open House

 Monroe County Sheriff's Office Animal Farm 14 Dec 2025
CHRISTMAS

17th Annual Rudolph APSMC 5K

 Southernmost Beach Resort 13 Dec 2025
SPORTS

Lower Keys Chamber Holiday Gala and Installation Dinner

 Tennessee Williams Theatre 3 Dec 2025
HOLIDAY

Christmas at Matt's Stock Island Kitchen & Bar

 7001 Shrimp Road, Key West, FL, United States, Florida 33040 24 Dec 2025
CHRISTMAS

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

 Sebago Key West 31 Oct 2025

Annual Holiday Ornament Paint Night, with Jess

 22&Co Key West 10 Dec 2025
DRAWING-PAINTING

Clay Walker in Key West

 Country Cruising 29 Oct 2025
LIVE-MUSIC

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

Fausto's Food Palace 12 Dec 2025
CHRISTMAS-PARADES

Southernmost Turkey Trot 5K

 The Southernmost Point Buoy 27 Nov 2025
THANKSGIVING