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

Special Offers In September

If you haven’t taken a Fury trip, you haven’t done Key West! Climb aboard for an adventure you’ll remember forever and the one experience that will complete your vacation. Check out our Flash Sales to see what kind of special offers we have on select trips!

Luggage with Key West attractions inside and an Old Time Trolley next to it

Key West Vacation Old Town Trolley Package

It’s time to get away and explore! Discover paradise and save up to 50% on our Key West Vacation Old Town Trolley Package. Hop aboard an open-air trolley and enjoy panoramic views of the Conch Republic, while friendly and knowledgeable guides highlight the rich history of 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.

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 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.

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 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!

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!

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.

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 get a bird’s eye view of paradise. Ocean dips are also available for our thrill-seekers.

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.

key west brewfest

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 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.

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!

Last Updated 11/23/2020