Key West Holiday Events

Key West Lighted Boat Parade 🎄

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

Running of the Elves

Key West 20 Dec 2025

Wesley House Holiday Village & Bike Ride

Coffee Butler Amphitheater 5 Dec 2025

The Lighting of the "Harbor Walk of Lights"

Conch Republic Seafood Company 26 Nov 2025

Best of Key West Jazz Concert Series

William Weech American Legion Post 168 - All Welcome 29 Nov 2025

17th Annual Rudolph APSMC 5K

Southernmost Beach Resort 13 Dec 2025

December Duo Holiday Concert: Irie Monte and Crispin Campbell

533 Eaton St, Key West, FL, United States, Florida 33040 13 Dec 2025

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 12 Dec 2025

European style Holiday Market

319 Duval Street, Key West, FL 6 Dec 2025

Time to Talk Turkey!

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

Key West Gardens 70th Anniversary Gala

Key West Garden Club 3 Dec 2025

Santa Visits the Hemingway Home & Museum! ✨

907 Whitehead Street, Key West, FL, United States, Florida 33040 20 Dec 2025

Holiday Market

319 Duval St, Key West, FL 6 Dec 2025

Thanksgiving at Four Marlins

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

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

A Very Tutu Christmas Trolley 2025!

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

Holiday Lights Conch Tour Train

Sigsbee Community Center 12 Dec 2025

Lower Keys Chamber Holiday Gala and Installation Dinner

Tennessee Williams Theatre 3 Dec 2025

Key West Thanksgiving Ultimate Adventure H2.O 🦃

631 Greene St, Key West, FL, United States, Florida 33040 27 Nov 2025

Holiday Lighted Boat Parade

The Perry Hotel & Marina Key West 14 Dec 2025

Thanksgiving Dinner

601 Front St, Key West, FL, United States, Florida 33040 27 Nov 2025

Reef Relief Annual Holiday Train

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

Lighting of the Bight

Key West Historic Seaport 26 Nov 2025

Watercolor Fundraiser with Tracey DeLellis at Alonzo's Patio Bar

Alonzo's Patio Bar 15 Dec 2025

Santa Run + Pilates Wellness Event

Blue Flamingo Resort Key West 13 Dec 2025

First Taste Monday: Boulevard Cherries Jubilee Quad

417 Southard St, Key West, FL 24 Nov 2025

Pet Photos With The Grinch

336 Duval St, Key West, FL, United States, Florida 33040 4 Dec 2025

Christmas on the Farm Open House

Monroe County Sheriff's Office Animal Farm 14 Dec 2025

Keys Choral Arts: Holiday Concert

Tennessee Williams Theatre 13 Dec 2025

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theatre 16 Dec 2025

Italian Night at the Movies: Light in the Piazza

Tropic Cinema 3 Dec 2025

Build-a-Bouquet

Sigsbee Community Center 24 Nov 2025

Kid's Crafts AT NIGHT: Elf Workshop

Sigsbee Community Center 10 Dec 2025

Winterfest

Sigsbee Community Center 4 Dec 2025

Celebrate Thanksgiving at the Key West Cooking Show

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

Christmas Eve & Christmas Day Lunch & Dinner at Yellowfin

5950 Peninsular Avenue, Key West, FL, United States, Florida 33040 24 Dec 2025

Petal-n-Palette Bubbles & Blooms - Holiday Floral Design Class

The Gardens Hotel Key West Florida 20 Dec 2025

Sail with Santa 🎅

631 Greene St, Key West, FL 33040-6624, United States 3 Dec 2025

FRLA Monroe Cheers to the Holidays!

Opal Key Resort & Marina 9 Dec 2025

Holiday Concert at Tennessee Williams Theatre

Tennessee Williams Theatre 14 Dec 2025

Christmas at Matt's Stock Island Kitchen & Bar

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

Yachtley Crew

Key West Theater 18 Feb 2026

Annual Holiday Ornament Paint Night, with Jess

22&Co Key West 10 Dec 2025

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

Fausto's Food Palace 12 Dec 2025

Southernmost Turkey Trot 5K

The Southernmost Point Buoy 27 Nov 2025