Key West Events September 2026: Things to Do, Festivals, Live Music & Weather
Planning a trip to Key West in September 2026? September is one of the quieter times of year in Key West, but don't mistake quieter for boring!
Between Womenfest Key West, the Just a Few Friends Jimmy Buffett Celebration, Key West BrewFest, live music, the Second Line Memorial Parade, fishing, snorkeling, sandbar trips and local events, there is plenty happening throughout the month.
If you're wondering what to do in Key West in September, what the September weather is like, or what events are happening in Key West in September 2026, here's what you need to know.
Key West Weather in September
September is still summer in the Florida Keys, so expect hot, humid and tropical weather.
Typical September weather in Key West:
Average high: 89°F
Average low: 79°F
Water temperatures are still very warm
September is part of our rainy season, but don't panic when you see rain on your weather app!
Rain and thunderstorms can be very localized in the Florida Keys. It may be raining on one side of the island and sunny on the other, and a forecast showing rain doesn't necessarily mean an entire day will be a washout.
September is also during Atlantic hurricane season, so it's always smart to keep an eye on the tropics as your vacation approaches.
What to pack for Key West in September: lightweight clothing, bathing suits, sunscreen, sunglasses, a hat, comfortable sandals, a reusable water bottle and a light rain jacket.
And trust me, don't underestimate the September heat!
Key West Events in September 2026
September 2–6: Womenfest Key West
Womenfest Key West returns September 2–6, 2026.
The five-day festival celebrates connection, creativity and island life with themed parties, pool gatherings, live music, DJs, art, tours, foodie events, sunset sailing, snorkeling and nightlife.
The 2026 theme is “Lost Women in the Arts.”
September 2–6, 2026
Various locations throughout Key West
Times vary by event
September 2–3: John Frinzi & Aaron Scherz
Jimmy Buffett fans can start the Labor Day celebrations early with singer-songwriters John Frinzi and Aaron Scherz.
Expect tropical Americana, country, folk and plenty of island influence.
September 2 & 3
7:00–9:00 PM
Key West Theater Listening Room
September 3–7: Just a Few Friends – Jimmy Buffett Celebration
One of the biggest Key West events in September 2026 is the third annual Just a Few Friends – Favorite Son Celebration, honoring Jimmy Buffett and his connection to Key West.
For five days over Labor Day weekend, Key West will be filled with live music, parties, special events, boating excursions and plenty of Parrothead fun.
September 3–7, 2026
Throughout Key West
There are MANY individual events throughout the festival. Here are some of the highlights you'll want on your calendar:
Thursday, September 3 – Cheeseburger Beach Battle & Concert
Kick off the weekend Key West style with cheeseburgers, a beach and live music.
Thursday, September 3
5:00–8:00 PM
South Beach
Friday, September 4 – Duval Street Party
Friday night brings the celebration right onto Duval Street.
Gary & the Landsharks will take over Duval as the festival recreates the spirit of the legendary 1998 Parrothead Street Party.
Friday, September 4 5:30pm
Duval Street
Expect live music, a BIG crowd and street closures in the area.
Friday, September 4 – First Fridays on Fleming
If you want to take a break from Duval, head over to Fleming Street.
Local galleries, shops and businesses stay open for an evening celebrating Key West's creative community.
Friday, September 4
6:00–9:00 PM
Fleming Street
Saturday, September 5 – Parrots & Margaritas 5K
Start Saturday morning with the Parrots & Margaritas 5K Run/Walk.
Saturday, September 5
8:00 AM
Key West
September 5–6 – Key West Open Water Swim
The CFK Pentathlon Swim Meet & Key West Open Water Swim takes place in the warm waters off Key West.
September 5–6
Higgs Beach
The weekend includes several open-water swimming events.
September 5–7 – Key West BrewFest
Beer lovers also have something to celebrate over Labor Day weekend.
Key West BrewFest returns September 5–7 with craft beer tastings, tap takeovers, pairings and special events at locations around the island.
September 5–7, 2026
Various Key West locations
Saturday, September 5 – Live Music at Sunset Pier
Saturday night brings live music to one of Key West's best waterfront locations.
Mike Stack & Friends open the stage.
The Wheeland Brothers take over the big stage later in the evening.
Saturday, September 5- 6:30pm -9:30pm
Sunset Pier
There are also pool parties, bar strolls, sunset sails and additional live music happening throughout Saturday.
Sunday, September 6 – Second Line Memorial Walking Parade
THIS is one of the signature events of the weekend.
The Second Line Memorial Walking Parade honors Jimmy Buffett as hundreds of fans make their way through downtown Key West.
Sunday, September 6, 2026
5:00–6:00 PM
Starts at 100 Duval Street
FREE
The parade travels down Duval Street, turns onto Southard Street and finishes at Truman Waterfront Park.
Howard Livingston & the Mile Marker 24 Band will help lead the Second Line.
Wear your tropical gear and join the celebration!
Sunday, September 6 – Party in the Park: Tribute to Bubba
Don't leave when the parade ends!
The parade leads directly into the Party in the Park: Tribute to Bubba at Truman Waterfront Park.
Sunday, September 6
6:00–10:00 PM
Truman Waterfront Park
FREE
Expect live music, food, drinks, vendors and a huge gathering of Jimmy Buffett fans.
The 2026 celebration includes performances from musicians with deep ties to Buffett and the Trop Rock world, including:
Mac McAnally
Will Kimbrough
Howard Livingston & the Mile Marker 24 Band
Mac McAnally is a longtime member of Jimmy Buffett's Coral Reefer Band, making this an especially fun night for Buffett fans.
Monday, September 7 – Labor Day Finale
The Jimmy Buffett celebration continues through Monday.
Rooftop Pool Party
Monday, September 7
1:00–4:00 PM
La Concha Key West
FREE
Then head back toward the water for one final evening of music.
Come Monday: Cayman & the Mango Men
Monday, September 7
6:00–8:00 PM
Sunset Pier
FREE
It's a pretty fitting way to wrap up five days celebrating Jimmy Buffett in Key West.
Monday Night Jazz Jams
Looking for some local live music during your September vacation?
Monday Night Jazz Jams take place at the William Weech American Legion Post 168.
Mondays throughout September
8:00 PM
American Legion Post 168
Local and visiting musicians come together, so every Monday can be a little different.
Key West Farmers Market
The Key West Farmers Market is a fun way to spend a Thursday afternoon.
Browse food, produce, seafood, art, handmade goods and other local vendors.
Thursdays throughout September
1:00–6:00 PM
Truman Waterfront Park
You're also in a great location to explore Truman Waterfront before heading downtown for sunset.
September 17 – Happy Hour with the Historian
History lovers can learn more about the presidential history of the Florida Keys during the Key West Art & Historical Society's Happy Hour with the Historian.
Thursday, September 17
Key West
The September program focuses on Presidents in the Florida Keys: Power, Politics, and Retreat.
September 19 – Walk on White
Want to experience a more local side of Key West?
Walk on White is a monthly art walk through the White Street arts district.
Saturday, September 19
White Street Arts District
Galleries, studios, shops and local businesses open their doors for an evening celebrating art and the Key West creative community.
Many locations also feature refreshments, music and special exhibitions.
September 27 – Sheriff's Animal Farm Open House
Traveling to Key West with kids?
The Monroe County Sheriff's Office Animal Farm on Stock Island opens to visitors for a special open house.
Sunday, September 27
1:00–3:00 PM
5501 College Road, Stock Island
Kids can see animals including sloths, capybaras, goats, birds and more.
Best Things to Do in Key West in September
You don't need a festival happening to have an amazing September day in Key West.
In fact, one of the best parts about visiting during the slower season is having more opportunities to experience the island without peak winter crowds.
And if there's ONE thing I recommend...
Take a Key West Sandbar Trip
Don't come all the way to Key West and never get out on the water!
Key West is a boating destination, and some of the most beautiful places are only accessible by boat.
A Key West sandbar charter takes you into the shallow turquoise waters surrounding the island where you can swim, relax and experience the Florida Keys beyond Duval Street.
Both private and shared sandbar options are available.
Go Snorkeling
September's warm water makes it a great time to snorkel.
Depending on the trip and conditions, you can explore the reef or snorkel in the beautiful Key West backcountry.
You can also combine snorkeling with other water activities on certain trips.
Book a Key West Fishing Charter
September is a great time to experience fishing in the Florida Keys.
Depending on what you're looking for, there are offshore, reef, wreck, flats and backcountry fishing options.
You can even combine fishing and a sandbar stop on certain private charters — a great option when part of the group loves fishing and the rest wants some sandbar time.
Go Lobstering
Florida's regular spiny lobster season is open throughout September.
Regular season runs from August 6 through March 31.
Make sure you have the appropriate Florida fishing license and understand current size limits, bag limits and harvesting regulations before heading out.
Take a Key West Sunset Cruise
There is something completely different about watching a Key West sunset from the water.
Choose from sailing trips, private charters, tiki boats and larger sunset cruises.
Visit Mallory Square for Sunset Celebration
The Mallory Square Sunset Celebration is one of Key West's most famous traditions.
Head down before sunset to see performers, musicians, local artists and vendors while watching the sun go down over the Gulf.
The celebration takes place every evening around sunset.
Explore Key West by Bike
September is a great time to explore beyond Duval Street.
Bike through:
Old Town
Historic Seaport
Truman Waterfront
Bahama Village
White Street
Key West's residential neighborhoods
Go early in the morning if you can — September afternoons are HOT!
Things to Do in Key West When It Rains
September weather can change quickly, so it's always good to have a few indoor activities in mind.
Try:
• Ernest Hemingway Home & Museum
• Key West Butterfly & Nature Conservatory
• Key West Shipwreck Museum
• Harry S. Truman Little White House
• Mel Fisher Maritime Museum
• Key West Aquarium
• Key West Lighthouse
A passing shower can also be the perfect excuse to grab some key lime pie and wait it out!
Does It Rain All Day in Key West in September?
This is one of the questions I hear ALL the time.
September is one of Key West's wetter months, but seeing rain on your weather app does not automatically mean it's going to rain all day.
Weather here can be incredibly localized and change quickly.
It can be pouring rain in one part of Key West while the sun is shining somewhere else.
If you're scheduled for a boat trip, stay in contact with your charter company. Local captains watch the weather and marine conditions closely and will make decisions based on what's actually happening on the water.
Is September a Good Time to Visit Key West?
If you're okay with the heat, September can be a fantastic time to visit.
It's part of Key West's slower season, so you'll generally find fewer crowds than during peak winter months.
September is especially fun if you visit over Labor Day weekend because Womenfest, Key West BrewFest and the Just a Few Friends Jimmy Buffett Celebration overlap, creating one of the liveliest weekends of the month.
The tradeoff?
It's hot, humid, rainy season and hurricane season.
Keep an eye on the weather, stay flexible and enjoy a more laid-back side of Key West.
Plan Your September 2026 Key West Vacation
Whether you're coming for the Jimmy Buffett celebration, Second Line Memorial Parade, Womenfest, Key West BrewFest, live music, fishing, snorkeling, a Key West sandbar trip or simply a tropical getaway, September has plenty happening.
And remember: Key West is so much more than Duval Street.
Some of the best experiences are waiting out on the water.
Looking for help finding and booking the right Key West excursions and water activities for your trip?
Visit Experience Key West:
I can help you find:
Key West sandbar trips
Snorkeling tours
Fishing charters
Fishing + sandbar combination trips
Sunset cruises
Private boat charters
Shared sandbar trips
Other Key West excursions and experiences
Save this Key West September 2026 events guide and check back as your trip gets closer. Event schedules, performers and times can change, and additional Key West events may be announced throughout the year.