Key West Events Calendar
Good times and good vibes are always on deck. Check out our activities and the local music scene at Ocean Key Resort and Sunset Pier.
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Oct19
Island Experiences
Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended b...
Date: October 16 -25, 2026Time: Varies by eventLocation: Key West (multiple venues)
Oct19
Food & Drink
Savor the Season
Celebrate Sober October with Ocean Key Resort and Best Day Brewing.
Date: October 1, 2026 - October 31, 2026Time: All dayLocation: Sunset Pier
Oct19
Island Experiences
Mrs. Roper Romp, Costume Contest
Get your caftans ready and that signature curly red wig for a groovy costume party on Sunset Pier.
Date: October 19, 2026Time: 5:00 PMLocation: Sunset Pier
Oct20
Island Experiences
Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles a...
Date: May 12, 2026 - December 31, 2026Time: Tuesday's, 2:00 pm – 5:00 pmLocation: Off-Site (Catamaran / Key West reef)
Oct20
Island Experiences
Tay Tay Tuesday, Life of a Showgirl
Join us for a family-friendly tribute to your favorite musical icon and showgirl.
Date: October 20, 2026Time: 6:00 PMLocation: Sunset Pier
Oct21
Music
Live at Sunset Pier – DJ Scott Gerke
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bite...
Date: Daily: October 21 - 24, 2026Time: 1:00 pm - 4:00 pmLocation: Sunset Pier