Events
It's not just another day in paradise! You'll find doings and happenings up and down the Keys, nearly every day of the year. Check out the latest fun and frolic below.
Only-In-The-Keys Festivals & Events
There’s always something happening in the Florida Keys & Key West, from eclectic festivals focusing on the area’s colorful history, arts and notable cuisine to events that celebrate the Keys’ unique environment, underwater adventures and quirky ambiance.
See Some Shenanigans
Featured
Key West
Fantasy Fest
-
Each October, Fantasy Fest transforms Key West into a colorful celebration of costumes, creativity, music, and performance. The multi-day festival was...
Featured
Key Largo
REEF Ocean After Hours - Waterlust Trivia #1
Tuesday, October 20, 2026, at 6 p.m. Put your marine science knowledge to the test during the Waterlust Trivia Challenge at the REEF Ocean Exploration...
Featured
Key West
TUTU SALSA SESSIONS
Tuesday, October 20, 2026. Celebrate one of Fantasy Fest’s most colorful traditions during Tutu Tuesday at Southernmost Beach Café, where beachfront...
Featured
Key West
Rum Revelations: A Cocktail Adventure
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
Featured
Key West
Key West History Through Five Craft Cocktails
-
Available October 20–24 and October 27–31, 2026, from 5 to 7 p.m. Raise a glass to Key West’s colorful past during Key West History Through Craft...
Featured
Key West
Heels For All with Paula Ali
-
Wednesday, October 21 and Thursday, October 22, 2026, from 1 to 2:30 p.m. Explore movement, character, and self-expression during Heels For All, a two...
Featured
Marathon
Marathon Yacht Club Game Day Fundraiser
Wednesday, October 21, 2026, beginning at 11 a.m. Gather around the tables for a day of friendly competition at the Marathon Yacht Club, all while...
Featured
Key West
LUV2GLOW: Liquid Frequency
-
Get ready to light up the night at LUV2GLOW: Liquid Frequency, a two-night electronic and dance music experience taking over Rick’s Key West on...
Featured
Key West
Photography Masterclass with Frank Stewart
Friday, October 23, 2026, from 1 to 3:30 p.m. Photographers can receive in-depth feedback on their work during a Portfolio Review with acclaimed...
Featured
Islamorada
Treasure Treat Night
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
Key West
Southernmost Playboy House - Beach Bunny Pool Party Bash
Friday, October 23, 2026, from 10:30 a.m. to 5:00 p.m. The Southernmost House throws an oceanfront, adults only pool party during Fantasy Fest, billed...
Islamorada
8th Annual Trunk or Treat Halloween Party
Saturday, October 24, 2026, from 6:00 to 8:30 p.m. The Village of Islamorada throws its 8th Annual Trunk or Treat Halloween Party on the Great Lawn at...
Featured
Key West
Screaming Green Halloween
Saturday, October 24, 2026, from 10 a.m. to 2 p.m. Celebrate Halloween with a green twist during Screaming Green Halloween at the Key West Tropical...
Key Largo
MarineLab's Haunted Lagoon
Saturday, October 24, 2026 from 6:00 to 8:30 PM. We dare you to snorkel MarineLab's Haunted Lagoon. Spooky science, ghoulish games and terrifying...
Key West
The Hangover "But Did You Die?" Pool Party at Somo's Pineapple Pool
Sunday, October 25, 2026, from 1:00 to 4:00 p.m. The Pineapple Pool at Southernmost Beach Resort hosts a Hangover themed pool party on the closing day...
Featured
Key West
Sheriff’s Animal Farm Open House
-
Enjoy a fun and memorable family outing at the Monroe County Sheriff’s Animal Farm on Stock Island. Open the second and fourth Sunday of each month...
