The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
Events calendar provided by www.fla-keys.com.

Events in the Florida Keys for September, 2024
Year: Month:  
March 15 to September 13,  in Key West
Key West Art & Historical Society: Flora & Fauna - Early Naturalists in Florida
Enjoy the “Flora & Fauna: Early Naturalists in Florida” exhibit through September 13 at Key West Museum of Art & History's Custom House, Museum, 281 Front Street. The exhibit includes short biographies of the principal naturalists working in the Florida Territory in the early nineteenth century alongside representations of their Florida-inspired works. Their observation of plants and animals was an art as well as a science.


June 01 to September 01,  in Key West
Key West Art & Historical Society: Beaches, Creatures & Cowboys - Florida Movie Posters Exhibit
Forty classic Florida film posters are on display at the Customs House Museum, 281 Front St., Friday in the "Beaches, Creatures & Cowboys: Florida Movie Posters" exhibition celebrating filmmaking in Florida. The classic posters that form part of the display include artwork for “Beneath the 12 Mile Reef,” “Cocoon,” “Flipper,” “Operation Petticoat and more" The exhibit runs through September 1, 2024.


August 29 to September 02,  in Key West
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, and the lavish BrewFest Signature Tasting Festival held Saturday, Aug. 31 at Southernmost Beach Resort, 1319 Duval St. Tickets to various festival events are available online.


August 30 to September 02,  in Key West
Just a Few Friends - Key West Favorite Son Celebration
Join the citizens of Key West and fans from around the world to celebrate the life and music of Jimmy Buffett throughout Labor Day Weekend. Events planned so far include a cheeseburger contest and welcome party; a bubbles brunch; walking tours; a 5k run/walk; a margarita bar crawl and scavenger hunt; and on Sunday, the Second Line Memorial Walking Parade and free outdoor celebration and concert at Truman Waterfront Park. Will Kimbrough, co-writer of "Bubbles Up," will be one of the performers, along with some of Key West's best singer-songwriters. On Monday, plans include a sunset cruise and a Farewell but not Forgotten party. All proceeds from $30 commemorative parade passes go to support Bahamas Village Music Program and Reef Relief.


September 01,  in Islamorada
History of Diving Museum: Summer Guided Tours
In honor of Labor Day Weekend, guided tours are offered at 11 a.m. and 2 p.m. Find out the interesting stories behind all of the exhibits. The tours are included with the price of admission. The museum is located at mile marker 82.9 bayside.


September 01 to November 30,  in Key West
Key West Tropical Forest & Botanical Garden: Scarecrows in the Garden
Get your spooky on at the 6th annual Scarecrows in the Forest Art exhibition and Contest. Around the corner, in a meadow or right in front of you, made from natural, recycled and repurposed material, scarecrows are found throughout the Tropical Forest & Botanical Garden. The exhibit runs Sept. 1-Nov. 30.


September 01,  in Key West
Just a Few Friends Key West: Second Line Procession
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.


September 01,  in Key West
Just a Few Friends Key West: Party in the Park
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.


September 01,  in Islamorada
Florida Keys Brewing Co.: Labor Day BBQ & Brews
Everyone's welcome in the Beer Garden from 11 a.m. to 7 p.m. for brews and BBQ from Pop's Smoke Shed. Caitlin Young performs live 2 to 5 p.m. Sign up by 3:45 p.m. for the Corn Hole Tournament that starts at 4 p.m.


September 02,  in Key West
Just a Few Friends Key West: Nautical Wheelers - A Tribute to Jimmy Buffett Featuring Roger Bartlett
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.


September 02,  in Islamorada
Labor Day Memorial Celebration at Islamorada Hurricane Monument
The Matecumbe Historical Trust holds its annual Labor Day Service on Monday, Sept. 2 starting at 9 a.m. at the Islamorada Hurricane Monument, mile marker 81.5. The public is invited to join in memory of the those who perished in the 1935 Hurricane and for the unveiling of the 1935 Hurricane Map. The Hurricane Monument memorializes hundreds of American Veterans and local citizens who died in the Hurricane of Sept. 2, 1935.


September 04 to September 08,  in Key West
Womenfest Key West
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.


September 07,  in Islamorada
Swim for Alligator Lighthouse
Swimmers have up to seven hours to complete the eight-mile roundtrip course out and back around Alligator Reef Lighthouse, ranked as one of the toughest swim challenges in the world. The course features an in-water start and a beach finish, ending shoreside during this tropical open-water swimming event. The competition raises funds for the restoration of the 151-year-old Alligator Reef Lighthouse, located in the Atlantic Ocean off Islamorada.


September 07,  in Marathon
Marathon Community Theater: Story Slam
The theater hosts Story Slam on Saturday night at 7 p.m. All are welcome to attend and share a story or listen to others on the theme, "What Was I Thinking?" There'll be a $50 cash prize for the best story. Free admission. 5101 Overseas Hwy.


September 07,  in Key West
Womenfest Key West: Fire & Ice Fantasy Prom
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.


September 08,  in Key West
Sheriff’s Animal Farm Open House
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.


September 12,  in Islamorada
Florida Keys Brewing Co.: I.CARE's Ocean Trivia
Join I.CARE and Key Dives at the Florida Keys Brewing Company, 81611 Old Hwy, 6:30 p.m. to test your knowledge on all things ocean, specifically megafauna in collaboration with World Dolphin Day. Find six of your closest friends to form a team and a night of craft beer and ocean-related fun. The winning team receives a swag basket from the Florida Keys History and Discovery Center.


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


September 14,  in Islamorada
Island Grill: Full Moon Pirates Beach Party
It's full moon madness at Island Grill's pirate bash with two live bands, a DJ, the Island Grill dancers and food and drink specials. Free parking and free dock space for those arriving by boat. MM 85.5 oceanside starting at 7:30 p.m. $18 tickets available online or at the door.


September 15,  in Key Largo
Key Largo Artisans Market: Children's Fair
A free Children's Fair opens at 11 a.m. during the regular Sunday Key Largo Artisans Market, held at Key Largo Civic Club, 209 N. Ocean Dr. Kids can enjoy a puppet show, bounce house, face painting, cool reptiles, story time, a Key Largo fire truck exhibit, photo booth, arts and crafts and more. There is to be a kids scavenger hunt to be entered in a drawing for a dolphin swim for two from Dolphins Plus, along with other raffle prizes.


September 15,  in Key West
Key West Theater: Pokey LaFarge
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.


September 18,  in Islamorada
History of Diving Museum: Immerse Yourself - Salvage Diving in the 20th Century
Join the History of Diving Museum at 7 p.m. for the monthly Immerse Yourself presentation. The topic is Salvage Diving in the 20th Century with Julia Sokolow, Community Relations Specialist at the Museum. During her time at the Museum, Julia has had the privilege of using the same style Mark V diving equipment that will be discussed in the presentation. She'll cover the evolution of salvage diving in the 20th century, including how divers first learned to reach the depths safely, how an underwater rescue was performed at 240 feet, how the CIA went as deep as 16,500 feet to retrieve a Soviet submarine in secret and more. Free to attend. Register to attend in person or on Zoom. MM 82.9 bayside.


September 19,  in Key West
Key West Art & Historical Society: Happy Hour with the Historian
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.


September 19,  in Islamorada
Morada Way Third Thursday Art Walk
The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate the arts and culture in the Florida Keys. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.


September 20 to September 22,  in Islamorada
Herman Lucerne Memorial Backcountry Fishing Championship
Named after the man known affectionately as “Mr. Everglades,” anglers target fish within the boundaries of Everglades National Park, fishing areas that Lucerne favored, and are challenged to catch at least one tarpon, redfish, snook, sea trout, snapper, bonefish and black drum or bass with the goal being to catch all seven species. Awards are given in 22 individual categories at a ceremony hosted at the Islander Resort.


September 20,  in Marathon
Marathon Community Theater: Dramatic Wine Tasting
Join others from 6 to 7 p.m. at Marathon Community Theater to sip and compare tastes of four different Chardonnay wines. $15 admission at the door. 5101 Overseas Hwy.


September 21,  in Key West
Key West Tropical Forest & Botanical Garden: Nature is Art Children's Workshop
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.


September 21,  in Key Largo
Wesley House Family Services Pickleball Tournament
Enjoy a day of fun and philanthropy at the inaugural Pickleball Tournament to benefit Wesley House Family Services. The tournament is a round robin style event based on players' skill levels with top teams advancing to the playoff round. Check-in at 9 a.m. with the tournament starting at 9:30 a.m. Registration fees include an event shirt, swag bag, plus free hamburgers, hot dogs, beer, mimosas and bloody Mary's. The deadline for player registration is Sept. 13th. The event takes place on the NEW pickleball courts at Key Largo Community Park, 500 St. Croix Place.


September 22,  in Key West
Sheriff's Animal Farm Open House
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.


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


September 27 to September 28,  in Key West
Key West Paddle Classic
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.


September 27 to September 28,  in Islamorada
Conch Scramble Charity Golf Tournament
The Conch Scramble is a charity golf tournament that uses boats instead of golf carts. Costumed teams boat to "holes" located at area marinas, bars and restaurants where players tee off from land to hit holes situated in the water. The legendary kick-off party - open to the public - takes place on Friday, Sept. 27 from 5 to 9 p.m. at SD Marine, mile marker 85.5 bayside, with the tournament on Saturday. Spectators can watch the wacky play from several favorite Islamorada watering holes on Saturday including Lorelei, Marker 88, and Oceanview Inn.


September 27 to September 28,  in Marathon
Sword Fest
Warriors on the Water, a group that funds and facilitates providing an outlet in nature for veterans through positive fishing experiences, presents Sword Fest, the ultimate swordfish fishing battle. Lines in at 5 a.m. Friday 9/27 with weigh in from 3 to 7 p.m. on Saturday 9/28 at Two Conchs Bait & Tackle, 11499 Overseas Hwy. An awards ceremony follows at 7:30 p.m. at Key Colony Inn, 700 West Ocean Dr., Key Colony Beach. With 30 boats entered, 1st place heaviest swordfish pays $10,000 and 2nd place $4,000. Optional entries available with additional fees for big payouts. All tournament proceeds benefit Warriors on the Water.


September 28,  in Marathon
Marathon Community Theater: Story Slam
The theater hosts Story Slam on Saturday night at 7 p.m. All are welcome to attend and share a story or listen to others on the theme, "When a Dream Came True...or Didn't." There'll be a $50 cash prize for the best story. Free admission. 5101 Overseas Hwy.




The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax
[email protected]

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