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Things to Do in Key West in September

Fury Things to Do in September Meme for Blog

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!

Fury Snorkel September

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.

Fury Bike Rental September

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Dolphin Watch Eco Tour Eco Tour • Backcountry Snorkel
  • 9:00am, 12:30pm
  • 3 hrs
  • low
  • Beverages
Save 10% $67.46 Reg. $74.95
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Dolphin Watch Sunset Cruise Combo Eco Tour • Backcountry Snorkel • Sunset
  • 4:30pm
  • 3 hrs
  • low
  • Beverages
Save 10% $67.46 Reg. $74.95
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Double Dip Snorkel Sunset Combo Snorkel 2 Reef Locations
  • 4:30pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $44.95 Reg. $49.95
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Double Dip Snorkel Trip Snorkel 2 Reef Locations
  • 9:00am, 12:30pm
  • 3 hrs
  • moderate
  • Beverages
Starting at $36.85 Reg. $40.95
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Glass Bottom Boat & Sunset Combo Reef Eco Tour
  • 5:30pm
  • 2 hrs
  • low
  • Snack Bar
Save 10% $43.15 Reg. $47.95
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Island Adventure & Sunset Cruise Combo Eco Tour • Snorkel • Kayak • Paddleboard
  • 3:30pm
  • 4.5 hrs
  • moderate
  • Food & Beverages
Save 10% $98.95 Reg. $109.95
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Island Adventure Eco Tour Eco Tour • Snorkel • Kayak • Paddleboard
  • 9:30am
  • 4.5 hrs
  • moderate
  • Food & Beverages
Save 10% $89.95 Reg. $99.95
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Key West Parasailing Fly Two or Three at a Time
  • 1 hr
  • low
Save 10% $49.45 Reg. $54.95
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Key West Snorkeling Morning Reef Snorkel
  • 9:30am
  • 3 hrs
  • moderate
  • Beverages
Save 10% $36.85 Reg. $40.95
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Key West Sunset Cruise Sunset Cruise • Champagne
  • 6:00pm
  • 2 hrs
  • low
  • Beverages
Save 10% $35.95 Reg. $39.95
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Save Up To $15
Land and Sail Package Trolley Tour • Sunset Sail
  • low
$64.95 Reg. $80.40
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Save Up To $11
Land and Sea Package Trolley Tour • Glass Bottom Boat
  • low
$64.95 Reg. $76.40
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Reef & Ritas Snorkeling Trip Afternoon Reef Snorkel
  • 1:00pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $43.15 Reg. $47.95
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Rum & Reggae Afternoon Reef Snorkel • Sunset Sail
  • 4:30pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $44.95 Reg. $49.95
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Ultimate Express Jet Ski • Parasail • Mini Water Park • Banana Boat
  • 11:00am, 3:00pm
  • 3.5 hrs
  • moderate
  • Food & Beverages
Save 10% $107.95 Reg. $119.95
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