Calendar of Events

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


Ninth Annual Key West Brewfest
Thursday, August 30 – Monday, September 3, 2018 EST
More than 150 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the offered activities.

46th Annual Phil Peterson’s Key West Poker Run
Friday September 14, 2018 – Sunday, September 16, 2018 EST
Motorcyclists from throughout the United States are to travel one of America’s most scenic highways to raise money for charity. Riders traverse the Overseas Highway (U.S. Highway 1), the 113-mile roadway from mainland Florida to Key West that features 42 bridges and long vistas of breathtaking open water.


39th Annual Key West Fantasy Fest
Friday, October 19, 2018 – Sunday, October 28, 2018 EST
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.

Motown “Let’s Get it On” Dance Party at Sunset Pier
Wed, Oct 24th
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.

Rockabilly “Shake, Rattle & Roll” Party at Sunset Pier
Thur, Oct 25th
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.

Fri, Oct 26th
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 . Doors open at 8 PM; Contest starts at 9:30 PM; For entry information contact the Sunset Pier 305-295-7047 or


37th Annual Key West World Championship Races
Sunday, November 4, 2018 – Sunday, November 11, 2018 EST
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.