Planning a trip to Key West in September? Check out these top things to do during September in Key West!

key west brewfest

Sample Brews at the Annual Key West BrewFest

August 31 – September 4

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 200 different beers throughout the weekend, 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. This event is one of the top things to do during September in Key West.

Attend the Annual Womenfest Celebration

September 6-10

At this southernmost party for lesbians and their friends, you’ll find a wide range of fun activities, including pool parties, cornhole tournaments 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!

Fury Blue Golf Cart Rental at the beach

Explore Key West on a Fury Golf Cart

Get the most out of your dream vacation by spending less time walking and more time sightseeing. Ride around the Conch Republic like a true local with our eco-friendly electric and gas-powered Golf Cart rentals. Enjoy the open-air and cool sea-breeze as you weave through the tight streets of Key West with our premier roadworthy rentals. Enjoy the thrill of cruising down Duval Street, island-style, and the convenience of getting to your next location with speed and ease. With a variety of rentals available accommodating up to six passengers, Fury’s Key West Golf Cart rentals provide the ideal transportation experience for your entire party. Our rentals are frequently maintained ensuring the safest and smoothest ride possible. This fun and easy way of exploring Key West is guaranteed to add to your unforgettable island adventure! Make sure to add this activity to your list of things to do during September in Key West!

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. Head to Higgs Beach and enjoy one of the top things to do during September in Key West!

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!

truman little white house

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 Truman’s 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.

key west aquarium touch tank

Cool Off In The Newly Air-Conditioned Key West Aquarium

Fury takes you to some of the best reefs on the water, so complete your Florida Keys eco-experience by learning about local marine life on land! The touch tank and shark exhibits are a must see for kids and adults, making it one of the top things to do during September 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 1200 Duval Street. 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.

Key West Private Catamaran Charters in Paradise

Discover the pristine blue waters of Key West aboard your very own private charter. We offer a fleet of high-performance catamarans that can transport your party on a private boat excursion of your choice for a truly unforgettable experience. Private Charters are completely customizable for your group and can include catering, full bar, live bands and picture packages. Whether you’re looking for a relaxing full-day on the water sipping your favorite cold beverage, or an adventurous half-day excursion, our team is prepared to help you plan the perfect day in paradise and experience one of the top things to do during September in Key West!

Dolphin Watch & Backcountry Snorkeling

Get a glimpse of beautiful Bottlenose Dolphins in their natural habitat on this incredible Key West Dolphin Watch & Snorkel eco-tour. Fury’s expert guides will teach you everything there is to know about the friendly mammals of the sea. Then enjoy some backcountry snorkeling and discover the world living underwater. This perfect family experience is guaranteed to leave lasting memories and serve as a top thing to do during September in Key West!

Key West Parasailing

Parasailing Over Paradise in Key West

Enjoy panoramic views of Key West with our exciting Parasail tour. Experience this tandem or triple adventure with friends and family, as the tropical breeze lifts you safely into the air. Soar above the emerald blue waters to get a bird’s eye view of paradise. Ocean dips are also available for our thrill-seekers.


Last Updated 12/21/2023