Key West Holiday Events

2025 Fantasy Fest Parade Viewing Party @ First Flight

First Flight Island Restaurant & Brewery 25 Oct 2025

Captain Morgan's Masquerade March

Fleming St, Key West, FL 33040, United States 24 Oct 2025

Puddles Pity Party at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 28 Sep 2025

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

Wesley House Holiday Village & Bike Ride

Coffee Butler Amphitheater 5 Dec 2025

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 12 Dec 2025

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

423 Caroline street, Key West, FL, United States, Florida 33040 21 Oct 2025

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

Rick's Bar 22 Oct 2025

Crystal Gayle

Key West Theater 21 Nov 2025

Sloppy Joe's Slumber Party

Sloppy Joe's 22 Oct 2025

Great Gatsby NYE 2026

First Flight Island Restaurant & Brewery 31 Dec 2025

17th Annual Rudolph APSMC 5K

Southernmost Beach Resort 13 Dec 2025

Christmas on the Farm Open House

Monroe County Sheriff's Office Animal Farm 14 Dec 2025

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

Sebago Key West 31 Oct 2025

Berkshire Hathaway Parade of Homes Mega Open House Event

922 Caroline Street, Key West, FL, United States, Florida 33040 23 Oct 2025

Clay Walker in Key West

Country Cruising 29 Oct 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

Midnight MAss Fantasy Fest

Island House Key West Gay Hotel & Resort 24 Oct 2025

Key West trip with the Barefoot Bay Travelers Club

Fairfield Inn & Suites by Marriott Key West at The Keys Collection 15 Oct 2025