Calendar of Events
Oct19Mrs. 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, 2026
Time: 5:00 PM
Location: Sunset Pier
Oct20Savor the Season
Celebrate Sober October with Ocean Key Resort and Best Day Brewing.
Date: October 1, 2026 - October 31, 2026
Time: All day
Location: Sunset Pier
Oct20Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
Oct20Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.
Date: May 12, 2026 - December 31, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Oct20Tay Tay Tuesday, Life of a Showgirl
Join us for a family-friendly tribute to your favorite musical icon and showgirl.
Date: October 20, 2026
Time: 6:00 PM
Location: Sunset Pier
Oct21Live 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 bites.
Date: Daily: October 21 - 24, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
Oct22SpaTerre VOYA Treatments
Relax and rejuvenate the natural way! VOYA Organic Seaweed Treatments.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, All day (by appointment)
Location: SpaTerre
Oct22Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Oct22Romance at Hot Tin Roof
Add some romance to your dining experience with a chilled bottle of Lallier Reserve Brut champagne and your table decorated with rose petals
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, During Hot Tin Roof dining hours
Location: Hot Tin Roof
Oct22Ocean Key Lime Bike Tour
Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
