Calendar of Events
Oct26Live at Sunset Pier – The 4 Amigos
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: October 5, 2026 / October 12, 2026 / October 26, 2026
Time: 6:00 pm - 8:00 pm
Location: Sunset Pier
Oct27Savor 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
Oct27Halloween Cocktails
Treat yourself to hauntingly delicious cocktails this spooky season at Hot Tin Roof.
Date: October 23, 2026 - October 31, 2026
Time: All day
Location: Hot Tin Roof
Oct27Live at Sunset Pier – Billy Ruegger
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Date: October 6, 2026 / October 13, 2026 / October 27, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
Oct27Double 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)
Oct27Live at Sunset Pier – Trop Rock Junkies
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: October 27 - October 28, 2026
Time: 6:00 pm – 8:00 pm
Location: Sunset Pier
Oct28Live at Sunset Pier – Claire Finley
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Date: October 14, 2026 / October 28, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
Oct29SpaTerre 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
Oct29Haunted 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)
Oct29Romance 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
