Ocean Key Resort & Spa by helicopter

Calendar of Events

There's never a dull moment here! View the Key West events calendar!

OCTOBER 19 - 28 2018

39th Annual Key West Fantasy Fest
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats.


OCTOBER 24 2018

Motown “Let’s Get it On” Dance Party at Sunset Pier
Get Down with Motown! The party kicks off on the BIG Stage with The “Soul Man” Robert Albury Band, followed by headliners PATRICK & THE SWAYZEES. Dance to all your favorite Motown grooves on the water at the World Famous Sunset Pier. FREE for everyone! Party starts at 6pm until 11pm. Sunset Pier - Zero Duval St.

Let's Get It On Dance Party flyer.


OCTOBER 25 2018

Rockabilly “Shake, Rattle & Roll” Party at Sunset Pier
Live Fast, Love Hard! Billy the Squid and Sea Cow Drifters kick it off on the BIG Stage along with DJ Greaser spinning Rockabilly Rock-N-Roll classics in all vinyl. FREE for everyone! Party starts at 7pm until 11pm. Sunset Pier - Zero Duval St.

Shake, Rattle, & Roll Flyer.


OCTOBER 26 2018

18th Annual Living Art Expo
A showcase of the human form as a living canvas. Contestant entries are open to Female, Male or Group models competing for the title of Best Overall Living Art of Fantasy Fest 2018 and $3000 in cash and prizes. Best Overall wins $1000 in cash. FREE General Admission event. VIP Backstage and Stage-front tickets available at keystix.com. . Doors open at 8 PM; Contest starts at 9:30 PM; For entry information contact the Sunset Pier 305-295-7047 or dining@oceankey.com


NOVEMBER 4 - 11 2018

37th Annual Key West World Championship Races
Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.