Welcome to the heart of hurricane season. But it’s still a great time to visit Key West. Just plan accordingly…. be flexible. You may have to reschedule or cancel. But, if the weather cooperates, September is a good time to visit Key West. School is back in session and there are fewer crowds. I say it’s the lull before the holiday high season. Honestly, as I always say, there really isn’t a bad time to visit Key West. Any month of the year is the perfect time to visit, right?

So, what are the best things to do in Key West in September? Let’s find out.

Weather

What can we expect with Key West weather? Hopefully, no hurricanes. But there is always a chance of tropical storms … and yikes, even a hurricane. That said, the average temperatures are in the mid 80s and only drops to an average low of 80 degrees at night. Still on the warmer side as the humidity is still high. Days can be sticky and nights not much cooler.

Looking for clear blue sunny days? September is overcast or mostly cloudy over 20 days a month and expect, on average over 3 inches of rain.

It can be a bit of a rainy season, this time of year… so what to Do on Rainy Days? So much to do!

Heading out to enjoy the waters around Key West? The water will still be warm with an average water temperature around 87 degrees.

Overall Month of September Vibe

The month of September is the best time to explore Key West. Hotel rooms, fingers crossed, have dropped a bit in price and the heat of the summer months is starting to move on. This time of year in the Conch Republic is filled with lots of activities. Top things to do?

Check out the amazing waters around Key West. Go snorkeling around the coral reef, dolphin watch, or even head out for a romantic sunset cruise.

Water Activities you must check out in Key West

The daylight hours during September are still long enough to enjoy a day filled with fun and then head out at night and explore Duval Street and all the live music it offers.

Wander around Old Town. Take a walking tour, or just wander the side streets and enjoy the blooming tropical flowers. A popular event in September is Brewfest. Always around Labor Day weekend, it’s a fun event for any beer lover.

As I have said, this time of the year is the lull, before the holiday season. The winter months bring in more people to enjoy the season of warm weather, keep in mind the average high is in the 70s. Who wouldn’t want to escape the cool north to warm up and enjoy the holidays? Keep in mind, September’s hotel prices are usually lower, since it’s not peak season… yet.

Another time of the year that is peak season, is Spring Break. Not as many college students, but I think the perfect time to enjoy outdoor activities with your family.

Top things in Key West not to miss

Activities in September

Key West Brewfest

Fans of beers and ales can sample about 150 of them while also discovering the flavors of the continental United States’ southernmost island. Activities ‘on tap’ include brew-focused dinners, pool parties and brunches, the lavish BrewFest Tasting Festival held Saturday on Key West’s South Beach, and other enticements.

Just a Few Friends Key West: Second Line Procession – September 1

Don’t miss this traditional walking “Second Line” parade in memory of the life and times of Key West’s favorite son, Jimmy Buffett. Walk wearing your best tropical attire and carry a sign if you choose. Meet in the lower 100 block of Duval Street starting at 4 p.m. The Second Line will step off at 5 p.m. following a route down Duval St., turning on Southard St., ending at Truman Waterfront Park for the “Party in the Park” with live music, food and camaraderie. Optional commemorative Parade Passes are available for purchase to support Key West charities.

Just a Few Friends Key West: Party in the Park – September 1

Celebrate Key West’s favorite son Jimmy Buffett at Truman Waterfront Park, 21 Quay Rd., after the Second Line Parade from 6 to 10 p.m. Enjoy live music by Keys musicians and Will Kimbrough, co-writer of Jimmy’s last single, “Bubbles Up.” There will be a marketplace atmosphere with numerous vendors, plentiful food choices, two full-service bars and an additional satellite bar just for Parade Pass holders.

Just a Few Friends Key West: Nautical Wheelers – A Tribute to Jimmy Buffett Featuring Roger Bartlett – September 2

Enjoy an extraordinary evening on Sunset Pier featuring Roger Bartlett, the original guitarist of Jimmy Buffett’s Coral Reefer band, along with Jockey Lord and Claire Finley. The free show takes place from 7 to 9 p.m. with food and drinks available for purchase.

Womenfest Key West – September 4 – 8, 2024

The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination. Activities range from beach parties, snorkeling, sunset cruises to live entertainment, an art workshop, the Fire and Ice Fantasy Prom and much more.

Womenfest Key West: Fire & Ice Fantasy Prom – September 7

The Fire & Ice Fantasy Prom is a new, major highlight to the entertainment lineup during the annual Womenfest Key West Celebration. The prom on Sat., Sept. 7, features a special live performance by female rock band Antigone Rising and local DJ Rude Girl, hosted by the American Legion, 803 Emma St. Dress to impress for this nostalgic and unforgettable night.

Sheriff’s Animal Farm Open House – September 8

Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.

Key West Art & Historical Society: Exhibit Opening Event Celebrating Key West Photographer Richard Weatherwax – September 13

Key West Museum of Art & History celebrates the opening of its newest temporary exhibition, “The Antic Humor of Richard Watherwax,” with a free reception on Friday, Sept, 13 from 5 to 7 p.m. The exhibition marks the photographer’s 90th birthday later this year. The opening event and exhibition, on display through Nov. 24, is to be held in the Bryan Gallery at the Custom House, 281 Front St.

Key West Theater: Pokey LaFarge – September 15

Singer/songwriter Pokey LaFarge makes music influenced by old-time country, blues, folk, Latin music and Western swing. On his new album Rhumba Country, LaFarge reveals his newly heightened devotion to making music that channels pure joy.

Sunset Pier: The Wheeland Brothers – September 17 – 18, 2024

The Wheeland Brothers bring their music filled with infectious good-time-energy and peaceful introspection to Sunset Pier for two free concerts. Their sound is a signature blend of surf rock, reggae, hip hop and acoustic pop. 6:30 to 8:30 p.m. on Tuesday and Wednesday nights. 0 Duval Street.

CFK Poetics: Kim Addonizio Poetry Reading – September 19

College of the Florida Keys kicks off its CFK Poetics series with a poetry reading by Kim Addonizio, the author of eight poetry collections, two novels, two story collections and two books on writing poetry: The Poet’s Companion (with Dorianne Laux) and Ordinary Genius. Her poetry collection Tell Me was a finalist for the National Book Award.

Key West Art & Historical Society: Happy Hour with the Historian – September 19

Join KWAHS historian Cori Convertito at Comedy Key West, 326 Whitehead St., for “Over the Seas and Across the Keys,” a history of Key West travel. The talk covers the early days of Key West when the only means getting there was by ship, until Henry Flagler’s railway reached the island city. Soon after, the advent of airplanes and automobiles continued to expand transportation options. Learn how each mode of transportation left its mark on Key West history.

Key West Tropical Forest & Botanical Garden: Nature is Art Children’s Workshop – September 21

Register your child in advance for this art workshop designed for parents and kids working together with provided materials to create special arts and crafts in the beauty of the garden. 10 a.m. 5210 College Rd.

Reef Relief: International Coastal Cleanup Day – September 21

Reef Relief is staging three ways and locations to participate in International Coastal Cleanup Day. The Land Lubbers cleanup is 9 a.m. to 11 a.m. at Boca Chica Beach, 354 Boca Chica Rd. Paddlers can sign up to go out with Danger Charters, and divers with Southpoint Divers and Grateful Divers. Click on the website link in this listing for more information.

Key West Theater: DUBÉ & DIAMOND, Dueling Impressionists – September 22

Immerse yourself in a whirlwind of legendary music and laughter with the DUBÉ & DIAMOND show for all ages! This daring duo of singing impressionists with a 5-octave range and very different musical styles promises you a one-of-a-kind experience. Accompanied by renowned guitarist, Réjean “Rej.E” LaChance, Martin Dubé and Steeve Diamond imitate the greatest hits of your favorite artists, from Adele to Tom Jones, Andrea Bocelli to Axl Rose, the Bee Gees to the Eagles and many more.

Sheriff’s Animal Farm Open House – September 22

Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.

Key West Paddle Classic – September 27 – 28, 2024

The 27th annual Key West Paddle Classic is a 12-mile open-water distance race around Key West that is open to paddlers on stand-up and prone paddleboards, outrigger canoes, surf skis, kayaks, pedal-craft kayaks, row and dory boats. Events are headquartered at Higgs Beach, 1000 Atlantic Blvd. Start time for the race is 9 a.m. Paddlers have up to five hours to complete the race, with a lunch and awards celebration starting at 1 p.m.

Key West Tropical Forest & Botanical Garden: Fall Migration Mania Birding & Wildlife Adventure – September 28

Flock to the historic Key West Tropical Forest & Botanical Garden to witness the natural wonders of the annual fall bird migration. For the 16th year, you can join others to be a citizen scientist learning as you enjoy species identification guided tours at the garden, at one of the most iconic bird and butterfly hotspots in the Lower Keys. Join the Birding ID and Census tour from 7:30 to 9 a.m.; and the Butterfly ID and Census tour from 10 to 11 a.m. $10 admission for each tour. Preregistration is suggested but will also be available at the door, which opens at 7 a.m. that day. 5210 College Rd.

Looking to head down toward the end of October? Be sure to check out all of the activities with Key West’s biggest festival… Fantasy Fest