Name: Key West trip with the Barefoot Bay Travelers Club
Start: 2025-10-15
End: 2025-10-17
Location: Fairfield Inn & Suites by Marriott Key West at The Keys Collection

2025 Fantasy Fest Parade Viewing Party @ First Flight

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

Captain Morgan's Masquerade March

Fri, 24 Oct at 05:30 pm Fleming St, Key West, FL 33040, United States

Puddles Pity Party at Key West Theater

Sun, 28 Sep at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

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

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

Custom House Holiday Concert & Bazaar

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

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

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

Crystal Gayle

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

Sloppy Joe's Slumber Party

Wed, 22 Oct at 11:00 am Sloppy Joe's

Christmas on the Farm Open House

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

Great Gatsby NYE 2026

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

17th Annual Rudolph APSMC 5K

Sat, 13 Dec at 07:00 am Southernmost Beach 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

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

Midnight MAss Fantasy Fest

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

Key West trip with the Barefoot Bay Travelers Club

Wed, 15 Oct at 07:30 am Fairfield Inn & Suites by Marriott Key West at The Keys Collection

Holiday events in Key West

Check out happening holiday events all around Key West, FL