Planning a trip to Key West in September? Don’t miss out on some of the most popular Key West events and island activities while you’re here. Check out these top things to do during September in Key West!
Fury BrewFest Sunset Cruise
Calling all CRAFT BEER lovers! Come enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun. You’ll party the night away on Key West’s original live music sunset sail while enjoying appetizers and beer from kickin’ local companies like Green Parrot Bar, Smokin’ Tuna Saloon, and Conch Republic Seafood Company.
Sample Brews at the Annual Key West BrewFest
Labor Day weekend is all about relaxation. At the Annual Key West Brew Fest, you can soak up island paradise and enjoy the holiday with a cold drink in hand. Featuring more than 60 different beers, you’ll find beer tastings, delicious food and live music for a fun and memorable experience. All proceeds from the event benefit the Key West Sunrise Rotary Club of the Conch Republic.
Enjoy a Picnic at Higgs Beach
September is the perfect time to enjoy a picnic at laid-back Higgs Beach. Located in Old Town, Higgs Beach offers volleyball nets, tennis courts, a dog park, a playground and more. Take in views of the crystal clear Key West waters from the beach’s wooden pier, sit back in a beach chair and sunbathe on the sandy shore at this family-friendly beach.
Attend the Annual Womenfest Celebration
At this southernmost party for lesbians and their friends, you’ll find a wide range of fun activities, including pool parties, competitive bull riding and special women-only events. Well known comedians, artists and other performers also travel to Key West for this annual event. Enjoy burlesque shows, sunset cruises and more!
Snorkel the Reef with Fury Water Adventures
Take in the beauty of Key West’s crystal clear waters during a snorkeling trip with Fury Water Adventures. Sail out to the living coral reef on a state-of-the-art catamaran, and then descend into the ocean using Fury’s unique Stairway to the Sea to view tropical fish and vibrant coral up close. Professional instruction and sanitized snorkeling gear are provided, and you can choose from a variety of morning, afternoon and combination snorkeling trips. Bring along your friends and family for a truly immersive island experience!
Check Out the Annual Key West Poker Run
Every year, more than ten thousand motorcycle riders from all over the United States take part in the Key West Poker Run. The riders travel from Miami to Key West while collecting poker cards and enjoying everything South Florida has to offer along the way. Prizes are awarded for the best hand. The ride culminates in several parties in Key West, featuring some of the city’s finest food, drinks and entertainment!
Redbone Celebrity Tournament Series
This is one of three tournaments in the annual Redbone Celebrity Tournament Series, aka The Trilogy, where anglers target tarpon, bonefish and game fish to win the “Flats Grand Slam.” The event raises funds for the fight against cystic fibrosis.
Spend an Afternoon at Truman Little White House
Although it doesn’t rain much in Key West, September is more prone to wet weather than other times during the year. The Harry S. Truman Little White House is a great place to spend a few hours indoors and to gain wonderful insight on his presidency. Learn about the legislation and policy that took place during his administration and especially the bills crafted during his multiple working vacations in Key West.
Explore Key West by Bike
While there are many water adventures in Key West to experience, there is also plenty to do on land. One of the best ways to see Key West at your own pace is to rent a bike from the Marriott Beachside Hotel. Definitely cruise the beautiful tree-lined streets near the Hemingway House, Fort Zachary Taylor State Park and Smathers Beach. For more information on bike routes, read our article about the top 10 places to see while biking in Key West.