Key West Events Calendar

From annual festivals to holiday celebrations, the fun never stops in Key West. We're looking forward to these upcoming Key West events. For details on any event or planning a holiday vacation, contact our local team! We're happy to provide nearby vacation rental recommendations and the inside scoop on all things Key West. 

key west pride

Key West Pride

Jun 7 2023 - 8:00am to Jun 11 2023 - 5:00pm
Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag shows by Key West’s top performers, a...Read more
vfw fishing tournament


Jun 16 2023 - 8:00am to Jun 18 2023 - 6:00pm
A family fun tournament, cash prizes are to be awarded for the heaviest catch of five target species -- mahi-mahi (dolphin fish), wahoo, tuna, snapper and grouper. Cash prizes are awarded for the heaviest catches of each including a first-place prize of 5 thousand dollars...Read more
mango fest key west

Mango Fest Key West

Jun 22 2023 - 10:00am to Jun 25 2023 - 8:00pm
Experience all things Mango through shopping, education and demonstrations. Stroll through Truman Waterfront Park to visit vendors, shop local shops, visit galleries, and order great food.Read more
key west key lime festival

Key Lime Festival

Jun 30 2023 - 7:00am to Jul 4 2023 - 11:00pm
Now, for its 10-year anniversary, the 2023 Key Lime Festival is revving up to celebrate the world’s most sensational citrus with a mouth-watering array of festivities across the very island where Key lime pie was conceived. From June 30-July 4, lovers of the lime can...Read more
Hemingway Days

Hemingway 5k Sunset Run & Paddleboard Race

Jul 22 2023 - 5:00pm
The Hemingway 5k Sunset Run & Paddleboard Race is to challenge competitors Saturday, July 23. Race begins 5 p.m., from Southernmost Beach, 1405 Duval St. Celebrate your accomplishment while easing sore muscles from the race with an all-levels yoga recovery session Sunday, free to all...Read more
Hemingway Look Alikes


Jul 20 2023 - 8:00am to Jul 22 2023 - 10:00pm
Dozens of stocky, bearded men resembling Ernest Hemingway are to return to Key West for the 2023 Hemingway® Look-Alike Contest. Staged at Sloppy Joe’s Bar, where it began some 40 years ago, the contest's preliminary rounds are slated for 6:30 p.m. July 20 and 21...Read more
key west tropical heat

Key West Tropical Heat

Aug 9 2023 - 9:00am to Aug 13 2023 - 8:00pm
Enjoy five days of sizzling happenings in the island city whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival’s intriguing events range from all-male theme parties, pool parties, clothing-optional events and adult-oriented entertainment showcase the island’s LGBTQ venues...Read more
fantasy fest

Fantasy Fest Key West 2022

Oct 20 2023 - 8:00am to Oct 29 2023 - 5:00pm
Started in 1979 by Key West Locals, this 10-day parade has turned into one of the best and biggest parties Key West has to offer!Read more
key west songwriters festival

Key West Songwriters Festival

May 1 2024 - 7:00am to May 5 2024 - 11:30pm
The Key West Songwriters Festival -the largest festival of its kind in the world. Since 1997 BMI has been a presenting sponsor of the festival and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five...Read more