There is always something going on in Key West, from the sublime to the outrageous

Street fair on Duval Street
Street fairs on Duval Street happen many times throughout the year, including Fantasy Fest, Hemingway Days, Pride Week, and Parrotheads in Paradise.

Throughout the year Key West hosts a wide variety of events – many of which are truly unique to the island.

Depending on the time of the year, you may see walking Key West’s streets: Hemingway look-alikes, Jimmy Buffet “parrotheads”, pirates, motorcycle aficionados, Bahamian Junkanoo performers, world-class sailors and fishermen, noted authors & writers, or scantily clad Fantasy Fest revelers.

Plus, every night, is the Sunset Celebration ( Key West sunset times ). More about the nightly Sunset Celebration at Mallory Square

Visit our  Key West Calendar of Events to learn about upcoming festivals, parades, parties, and celebrations.

And below are ideas for things to do in Key West almost every other day.

Ultimate Watersports Package

  3.5-hour trip includes light snacks, beverages, sailing, parasailing, jetskis, and big water toys Want

Waverunner Jet Ski Tours

  Have an absolute BLAST zooming across the water…all the way around the island of

Sunset Cruise – Glass Bottom Boat

  A great view – above and below deck. Air-conditioned comfort on this Key West

Sunset Sail – Wind & Wine

  An upscale sunset cruise aboard a traditional working schooner – serving premium wine, beer,

Sunset Sails – Schooners & Tall Ships

  Hoist the sails – if you’d like to lend a hand – aboard the

Sunset Sail – Booze Cruise

  Boat trip to see the Key West sunset  – with beverages and an island

Sunset Booze Cruise Concert

  Trop-rock into the sunset on a sailboat! Includes free-flowing beer, wine, margaritas, and snacks


  Like snorkeling, but you can breath underwater thanks to scuba air tanks floating on