September in Key West: When the Island Belongs to the Locals Again
September gets a bad rap.
Around most of the country, summer is winding down. In Key West? We are just getting comfortable. 🌴
The crowds thin out, restaurant reservations get easier, the water is still wonderfully warm, and some of my favorite island events start filling the calendar.
Labor Day weekend alone brings Jimmy Buffett celebrations, live music, street parties, beach events, and plenty of reasons to leave the car parked and wander.
Then Womenfest arrives.
Then art walks.
Then fishing tournaments.
Then another concert.
You get the idea.
If you have ever wondered what Key West feels like when things slow down just enough without actually becoming quiet, September might be your month.
Here is what is happening around the island.
📌 Bookmark This Page
September calendars have a habit of growing as the month gets closer.
Bookmark this guide and check back for updated schedules, event additions, times, and local recommendations.
My goal is simple: make this a page you can pull up whenever someone asks, “What should we do in Key West this September?”
Now for the fun part.
🌴 September 2 through 6
Key West Womenfest
Key West has always been a place where people can show up exactly as they are, and Womenfest celebrates that spirit beautifully.
Five days of entertainment, parties, workshops, community gatherings, and island experiences bring visitors from around the world together in Key West.
The 2026 theme, “Lost Women in the Arts,” adds a creative twist by recognizing women whose contributions to art and culture deserve more attention.
Whether this is your first Womenfest or your annual trip back to the island, expect plenty happening around town.
Dates: September 2 through 6, 2026
More Information:
https://www.keywestchamber.org/latest-community-news/key-west-womenfest-returns-september-2-6-2026
🎸 September 2 through 7
3rd Annual Just a Few Friends Festival
There may be places that love Jimmy Buffett. And then there is Key West.
The Just a Few Friends Festival returns for another Labor Day weekend celebrating the music, stories, friendships, and island lifestyle Buffett helped introduce to the world.
Expect live music, parties, food, storytelling, charity events, and plenty of Parrotheads wandering around town.
What makes this celebration special is that it happens in the place that inspired so much of the music.
You are not just listening to the songs. You are standing in them.
Dates: September 2 through 7, 2026
More Information:
https://www.keywesttourist.com/festivals-events/just-a-few-friends-key-west-2026/
🎶 September 2 and 3
John Frinzi & Aaron Scherz
If your idea of a perfect Key West evening involves great songwriting, good stories, and an intimate theater, add this one to the calendar.
John Frinzi and Aaron Scherz bring their island inspired sound to the Key West Theater for two nights.
This is exactly the kind of performance that works perfectly here.
Small venue.
Great music.
No rush.
Dates: September 2 and 3, 2026
Location: Key West Theater
More Information:
https://ourkeywest.com/key-west-events-calendar/
🇺🇸 September 3 through 7
Labor Day Weekend in Key West
Labor Day weekend is never exactly quiet around here.
Throughout the island you will find live concerts, waterfront parties, food events, running events, family activities, and nightly sunset celebrations.
My advice? Do not try to schedule every hour.
Pick a few things you really want to experience and leave plenty of room for whatever Key West throws your way.
That is usually where the good stories come from.
Dates: September 3 through 7, 2026
More Information:
https://www.keywesttourist.com/festivals-events/key-west-labor-day-weekend-2026/
🍔 September 3
Cheeseburger Beach Battle & Tribute Concert
Cheeseburgers.
Beach.
Music.
Key West.
Sometimes an event really does not need much explaining.
Southernmost Beach Resort hosts a beachside cheeseburger competition paired with live tribute music and plenty of island atmosphere.
Bring your appetite and your flip flops.
Time: 5 PM to 8 PM
More Information:
https://www.keywesttourist.com/festivals-events/cheeseburger-beach-battle-concert/
🎤 September 4
Duval Street Party with Gary & the Landsharks
Duval Street temporarily trades traffic for live music.
Gary & the Landsharks take over the 200 block of Duval for one of Labor Day weekend's biggest free parties.
Music in the street.
People dancing.
Food and drinks nearby.
And some truly spectacular people watching.
Very Key West.
Time: 5:30 PM to 9 PM
Location: 200 Block of Duval Street
More Information:
https://www.keywesttourist.com/festivals-events/duval-street-party-featuring-gary-the-landsharks/
🏃 September 5
Parrots & Margaritas 5K Run/Walk
You can always earn the margarita first.
The Parrots & Margaritas 5K welcomes serious runners, casual walkers, and everyone in between.
It is less about setting a record and more about starting the day outside with a little exercise and a lot of Key West energy.
Date: September 5, 2026
More Information:
https://visitfloridakeys.com/plan-your-trip/plan-book/event-calendar?key%5B23%5D=23&page=2
🏊 September 5 and 6
CFK Pentathlon & Key West Open Water Swim
If you have ever looked at the water surrounding Key West and thought, “I'd like to swim across that,” this weekend is for you.
Athletes take to the water for several open water distances, including:
• 800 yard swim
• 1 mile swim
• 2 mile swim
Even if you are staying dry, it is a fun event to watch and another reminder that so much of Key West life revolves around the water.
Dates: September 5 and 6, 2026
More Information:
https://visitfloridakeys.com/plan-your-trip/plan-book/events/cfk-pentathlon-swim-meet-key-west-open-water-swim-2026
🎷 Every Monday
Monday Night Jazz Jam
One of the best things about Key West music is that you never quite know who will show up.
Every Monday evening, local and visiting musicians gather at William Weech American Legion Post 168 for an old fashioned jazz jam.
Every night is a little different.
That is exactly the point.
September Dates: 7, 14, 21, and 28
More Information:
https://visitfloridakeys.com/plan-your-trip/plan-book/events/monday-night-jazz-jams
🥬 Every Thursday
Key West Farmers Market
If you want a little snapshot of everyday island life, spend a Thursday afternoon at Truman Waterfront Park.
The Key West Farmers Market brings together local food, produce, flowers, seafood, art, handmade goods, and plenty of familiar faces.
Grab something to eat, wander the waterfront, and stick around for sunset.
September Dates: 3, 10, 17, and 24
More Information:
https://visitfloridakeys.com/plan-your-trip/plan-book/events/key-west-farmers-market-1
📚 September 17
Happy Hour with the Historian
Key West history is rarely boring.
Presidents certainly have a long history with the Florida Keys, and the Key West Art & Historical Society dives into those stories during this month's Happy Hour with the Historian.
If you like discovering the stories behind the places you walk past every day, put this one on the calendar.
Date: September 17, 2026
More Information:
https://www.kwahs.org/event/hh-presidential-visits/
🎨 September 17
Walk on White
One of my favorite local evenings.
Every third Thursday, White Street turns into a casual neighborhood art walk as galleries, studios, boutiques, and businesses stay open late.
You can wander in and out, meet artists, see new work, grab a drink, and experience a side of Key West that has nothing to do with Duval Street.
No real agenda necessary. Just walk.
Date: September 17, 2026
Official Website:
https://www.walkonwhitekeywest.com/
🎣 September 29 through October 2
IGFA Permit Invitational
Permit are one of the most challenging fish in flats fishing, which makes this tournament especially impressive.
Elite anglers come to Key West to compete in the IGFA Permit Invitational while chasing one of the most frustrating and rewarding species on the flats.
Even if you do not fish, seeing the boats return and hearing the day's stories is worth checking out.
Dates: September 29 through October 2, 2026
More Information:
https://visitfloridakeys.com/plan-your-trip/plan-book/event-calendar?category%5B77%5D=77
🎶 September 30
Gov't Mule & Ziggy Marley
Now this is a way to close out the month.
Gov't Mule and Ziggy Marley bring the Dreaming the Same Dream Tour to the Coffee Butler Amphitheater.
Live music beside the water on a September night in Key West?
Hard to argue with that.
Date: September 30, 2026
More Information:
https://www.keywesttourist.com/festivals-events/
🌅 Every. Single. Night.
Mallory Square Sunset Celebration
I've seen more Key West sunsets than I could possibly count. I still stop for them.
Mallory Square's nightly Sunset Celebration brings together street performers, musicians, local artists, food vendors, handmade crafts, visitors, locals, and whatever the sky decides to do that evening.
Some nights are orange.
Some are pink.
Some look like someone turned the saturation all the way up.
And somehow they never get old.
Official Website:
https://www.mallorysquare.com/
🐓 KWT's September Advice
September is not the month to over plan Key West.
Choose the events you really want to experience.
Leave a few evenings open.
Walk instead of drive when you can.
Talk to the person sitting next to you.
Stay for sunset.
And if something interesting is happening down a side street, go see what it is.
That is usually how Key West works best.
Thinking About More Than Just Visiting?
This happens more often than you might think.
Someone comes down for a long weekend.
Then they come back for a week.
Then they start checking Zillow at breakfast.
And eventually the question becomes...
“Could we actually live here?”
If Key West real estate has ever crossed your mind, whether you are curious about a vacation home, investment property, full time move, or simply want to understand what different neighborhoods cost, I am always happy to talk.
No pressure.
Sometimes the first step is simply figuring out what is possible.
And in a market as unique as Key West, Who You Work With Matters.
Final Thoughts
September may technically be part of Key West's slower season.
But somebody forgot to tell the island.
Between Womenfest, Jimmy Buffett celebrations, Labor Day parties, waterfront concerts, art walks, fishing tournaments, farmers markets, and nightly sunsets, there is plenty happening from the first week of the month to the last.
And honestly?
That is exactly why I love September here.
You get a little more breathing room without losing any of the personality that makes Key West special.
Come down.
Slow down.
Stay awhile.
You Should Be Here,
🐓KWT🐓
