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A September 2024 to Remember! Top Things to Do This Month


Beer Lovers Unite!

Key West Brewfest Labor Day Weekend banner.

Join us for the Annual BrewFest from August 31 – September 4, hosted by Southernmost Beach Resort. The multi-day festival features fun filled events, from pool parties complete with Belly Flop Contests to beer pairing dinners and of course the signature beer tasting event on Sept. 2. The different events are hosted all over town so you’ll have the opportunity to explore the island at the same time. This is one of the top events of the year, and one you should definitely not miss! Check out their website for details and schedule of events!


Celebrate Womenfest Key West

Key West Womenfest banner.

For several thousand women, early September (6th -10th) in Key West means enjoying adventures in Atlantic Ocean and Gulf of Mexico waters, entertainment and parties with like-minded people and relaxation on an accepting subtropical island — all during the island city’s Womenfest.
Described as one of North America’s largest gatherings of lesbians and their friends, singles, couples and groups of women flock to Key West each year for  activities including dance parties, poolside gatherings, sailing and snorkeling, live music, comedy performances and more.
The Womenfest schedule begins with an opening night party –Subsequent offerings include a sunset dinner cruise on the clear Keys waters, late-night parties, a drag show featuring renowned female impersonators and gatherings at leading clubs. A “rock roller derby” and a flag football friendship game are planned for fans of high-energy sports. Check out the full list of scheduled events here! 

Go On a Seafoodie Adventure

Seafood Tours Key West

Seafood Tours Key West

Daily throughout September

Come hungry, leave happy. Key West Food Tours brings both tourists and locals another fabulous & fun-fact-filled walking tour highlighting the region’s incredibly fresh and local seafood. The 3 hr tour includes 5 mom & pop restaurants specializing in Key West’s “fruit of the sea” from local to pink shrimp and Florida spiny lobster. Book Here! 

Monday Fundays


Join us every Monday / 9pm at Mary Ellen’s Bar for the hilarious Drunken Spelling Bee! Hosted by Comedy Key West, you can eat and of course DRINK while testing your rusty spelling skills.


Key West Paddle Classic 2023 banner.

Come practice your paddleboarding prowess in the 26th Annual Key West Paddle Classic. Participants will race around the island, starting and finishing at Higgs Beach. Kick off starts Friday September and the race is Saturday. Check the website for all the event details!

When: September 29 – September 30, 2023

Where: Higgs Beach, Higgs beach, Key West, FL 33040