

Race World Offshore Championships
Experience the most powerful of water activities in Key West with the Race World Offshore World Championships. Watch as the world’s biggest and fastest boats reach speeds of up to 180 mph over the six-mile course on the Gulf side of the island. Over the season (May to November), teams from around the world compete in National Series Points races to determine the overall winner. Take a shore-side seat for this exciting watersport action.
Date
November 1 - 8, 2026
Time
Daytime (race schedule varies)
Location
Key West (Gulf side – six-mile course)
Race World Offshore WebsiteCalendar of Events
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
Oct21Live at Sunset Pier – Jerico Rockability Quartet
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: October 7, 2026 / October 14, 2026 / October 21, 2026
Time: 6:00 pm - 8:00 pm
Location: Sunset Pier
Oct22Savor 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
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)
Oct22Fantasy 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)
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)
Oct22Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Oct22Live at Sunset Pier - Reggae Lou & The Kind Buds
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: Thursdays: October 1 - October 29, 2026
Time: 6:00 pm - 8:00 pm
Location: Sunset Pier