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, 2023
Year: Month:  
August 31 to September 04,  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, Sept. 2nd on Key West’s South Beach at 1319 Duval St. VIP tickets ($100 per person) and general admission tickets ($45 per person) for the popular tasting festival are available online. Visitors and residents are advised to secure their Signature Tasting event tickets in advance before they sell out.


August 31 to September 02,  in Key West
Comedy Key West: Kevin Farley
Kevin Farley, brother of late comedian Chris Farley, brings his brand of "positive" stand-up comedy to Comedy Key West for three nights. Doors open 7:30 p.m.; showtime 8:30 p.m. Single tickets $30. 218 Whitehead St.


September 01 to November 30,  in Big Pine
Scarecrows in the Forest Art Exhibit and Contest
The Key West Tropical Forest & Botanical Garden is showcasing local artists’, community members’ and local students’ unique versions of the fall season’s Scarecrows in the Tropical Forest. The scarecrows, made from natural and recycled materials, may be discovered throughout the 15-acre garden. The exhibit, open 10 a.m. to 4 p.m. daily, will be a lesson in recycling, art talent and a contest with cash prizes for the entries. The Garden is located at 5210 College Road.


September 01 to September 03,  in Marathon
Florida Keys Heroes Salute Tribute Weekend
Military, fire rescue, police and medical personnel are to be honored with specially priced rooms at Hawks Cay Resort and recreational programs as part of an annual Heroes Salute Labor Day weekend. Highlights of the patriotic, “heroes in action” weekend include a family fun night, a special Heroes Tribute presentation, live entertainment by local musicians, the ability to access Hawk's Cay's Keys to Country performance on Sept. 3, a fireworks show, food, games and contests. On Saturday, Sept. 2, there is to be a 5k run/walk through Duck Key followed by a special "Touch a Truck" event featuring local first responders that are both open to the public as well as to the heroes attending the special Hawk's Cay weekend. The resort is located at 61 Hawk's Cay Blvd., Duck Key.


September 02,  in Key West
Shakedown on the Green -- Key West Island Market
The Shakedown on the Green: Key West Island Market takes place the first Saturday of every month on the Sunset Green Lawn at 24 North Hotel, 3820 N. Roosevelt. This family-friendly, Key West Island Market features local goods, artists, food trucks, $5 mimosas, and more. Free admission and free parking.


September 03,  in Key Largo
Caribbean Club: Flocks on the Rocks
Support the Florida Keys Wild Bird Center at Flocks on the Rocks, Sunday afternoon, Sept. 3 starting at 2 p.m. at the Caribbean Club. Enjoy live acoustic music by Edie James, Pusser's Pelican Rum Punch, food, raffles and more. Mile marker 104 bayside.


September 03,  in Marathon
Hawks Cay Resort: Keys to Country
Hawk's Cay Resort on Duck Key presents the next "Keys to Country" concert and resort package starring Craig Morgan & Friends appearing live on Sept. 3rd. Headliner Morgan's signature hits include "Redneck Yacht Club," "Bonfire," Almost Home," "Wake Up Loving You," and more. Other artists in the lineup include Marla Cannon and Shane Minor. The concert is limited to resort guests who book the Keys to Country package and attendees of the Heroes Salute Tribute Weekend. Hawk's Cay Resort is located at 61 Hawks Cay Blvd., Duck Key.


September 03,  in Key West
It's 5 O'Clock in Key West Second Line Procession: In Honor of Jimmy Buffett
Key West will honor Jimmy Buffett with a Second Line Procession starting at 5 p.m. at the corner of Front and Duval Streets. There is to be a commemorative stop at Margaritaville, then the procession will end at Truman and Duval. Participants are encouraged to wear tropical attire and leis. The event benefits the Bahama Village Music Program.


September 06 to September 10,  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 and sunset cruises, live entertainment, an art workshop and much more.


September 07,  in Key West
Key West Theater: Girly Burly Burlesque Show
The Girly Burly Burlesque Show is back for a special Womenfest production in the Back Stage Listening Room at the Key West Theater. The evening of bump and grind beauties that stars Mona Amour and the Key West Burlesque dancers is hosted by local favorite drag king sensation, Chief Peach. This will be a “one night only” performance not to be missed. Tickets $35 and $65, with two showtimes, 6 and 9 p.m. 512 Eaton St.


September 10,  in Big Pine
Sheriff's Animal Farm Open House
The family-friendly Sheriff's Animal Farm is open 1 - 3 p.m the second and fourth Sundays of the month. Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a lemur, an alpaca, a skunk, a prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located at 5525 College Rd. on Stock Island at the Sheriff's Office Headquarters complex.


September 10,  in Key Largo
Florida Keys Lionfish Derby and Festival
Hosted by Reef Environmental Education Foundation, the public is invited to attend the Lionfish Festival festival Sunday at Postcard Inn Beach Resort & Marina, at mile marker 84 oceanside. Enjoy lionfish cooking demonstrations, lionfish tastings, raffle prizes, art and more.


September 11,  in Key West
September 11 Remembrance
The Key West Firehouse Museum, in cooperation with the Key West Fire Department, will hold a remembrance for the victims of the tragedy of September 11, 2001 on Monday beginning at 8:30 a.m. at the museum, located at 1024 Grinnell St. The public is invited to attend.


September 12,  in Key West
24 North Hotel: Paint & Sip Night with Artist Lance Berry
Get ready to laugh and have a blast with the whole family or a couple of pals at Paint and Sip night with Key West artist, character and life-of-the-party, Lance Berry. Your $40 ticket includes your first drink, plus all the art supplies and instruction you'll need to create your own masterpiece. The class takes place the second Tuesday of the month at Republica Bar & Lounge at 24 North Hotel, 3820 N. Roosevelt Blvd.


September 13 to September 18,  in Key West
Big Gay Key West
Come to the island paradise of Key West for the Big Gay Key West gay men's social event with exclusive access to four beautiful, welcoming resorts: Island House, New Orleans House, Alexander's Guesthouse and Equator Resort. Enjoy reciprocal access to all of the guesthouses, which are a short walking distance from each other. Nightly happy hours, rotating pool parties at multiple resorts and bars with complimentary cocktails, hors d'oeuvers, 24/7 access to health club amenities at Island House as well as many surprises. Book event packages and lodging online.


September 13,  in Key West
Green Parrot Bar: Lovely Cruise, A Local Tribute to Jimmy Buffett
Join some of Key West's finest musicians for a 90-minute set of Jimmy Buffett's classics during a special tribute show at the Green Parrot starting at 5:30 p.m. 601 Whitehead Street.


September 14,  in Key Largo
John Pennekamp Coral Reef State Park: REEF Fish ID Talk
Representatives from REEF Environmental Education Foundation present a Fish ID talk at 11 a.m. in the Visitor Center auditorium. Learn how to identify the many species of fish you can spot while snorkeling the reefs within John Pennekamp Coral Reef State Park. Free with regular park admission. Mile marker 102.5 oceanside.


September 14,  in Key West
Key West Art & Historical Society: Happy Hour with the Historian
The next Happy Hour with the Historian, presented by Key West Art and Historical Society at Comedy Key West, takes place from 5 to 6 p.m. on Thursday the 14th. Attendees receive a complimentary drink and are treated to a short presentation titled Clear Havanas: Key West's Cigar Industry, about the rise and fall of the cigar-making industry in Key West. Tickets $15. 218 Whitehead St.


September 15 to September 17,  in Islamorada
Herman Lucerne Memorial Backcountry Fishing Championship
Named after the man known affectionately as “Mr. Everglades,” the event is headquartered at the Islander Resort. Anglers target fish in multiple species only in the boundaries of Everglades National Park, fishing areas that Lucerne favored. Anglers are challenged to catch at least one tarpon, redfish, snook, seatrout, snapper, bonefish, and black drum. Awards are given in 22 individual categories.


September 15,  in Islamorada
Key Dives: World Cleanup Day 2-Tank Dive
Key Dives is hosting a FREE 2-tank dive for participants in a marine debris cleanup in honor of World Cleanup Day. The only charges will for be for nitrox or any dive gear that is needed. Funding to support this marine debris cleanup dive is provided by the National Marine Sanctuary Foundation. Divers check in at 7:30 a.m. and return at 12 p.m. Please register by calling Key Dives at 305-664-2211.
Contact: 305-664-2211
Email: [email protected]

September 15,  in Key Largo
John Pennekamp Coral Reef State Park: Restoring Corals Talk with Coral Restoration Foundation
Representatives from Coral Restoration Foundation present a talk on coral restoration efforts on our Florida Keys reef at 1 p.m. in the Visitor Center auditorium. Learn about ongoing efforts to repopulate the reef with nursery raised coral and scientific innovations to help corals survive and thrive. Free with regular park admission. Mile marker 102.5 oceanside.


September 16,  in Islamorada
Islamorada Boutique Poker Run
Stop in at each of five participating boutiques between noon and 6 p.m. to build your winning poker hand for a chance at the grand prize of $250 in gift cards. The boutiques are: Otherside Boardsports, Evolve, Heed, Mrs. Monroe and the Banyan Tree. Entry is $10 to benefit Castaways Against Cancer and includes a five card poker hand. You'll find a dealer at each boutique, where you'll pull a card from the deck that is recorded on your scorecard. When your hand is complete, head to Florida Keys Brewing Company to turn in your score card no later than 6 p.m. The Brewery is located at MM 81.6 in the Morada Way Arts District.


September 20,  in Islamorada
History of Diving Museum: Monterey Abalone Divers
This month's Immerse Yourself presentation is virtual. Sign up to hear from Tim Thomas, Monterey Bay area historian. He takes participants through the fascinating history of Monterey Bay's Japanese abalone divers, who used traditional methods as well as diving helmets to hunt for abalone in the cold waters of the California coast. To watch with others, there will be a viewing room at the History of Diving Museum during the Wednesday night presentation that begins at 7 p.m. Or, sign up to watch on your computer.


September 21 to September 24,  in Marathon
Marathon International Bonefish Tournament
The 64th annual Marathon International Bonefish Tournament starts with a registration and captains meeting Thursday at 4 p.m. at Overseas Pub & Grill, located at 3574 Overseas Hwy, oceanside, followed by three days of fishing. Contact Barbara Hewlett at 305-304-8682.
Contact: [email protected]


September 21,  in Key Largo
John Pennekamp Coral Reef State Park: REEF Fish ID Talk
Representatives from REEF Environmental Education Foundation present a Fish ID talk at 11 a.m. in the Visitor Center auditorium. Learn how to identify the many species of fish you can spot while snorkeling the reefs within John Pennekamp Coral Reef State Park. Free with regular park admission. Mile marker 102.5 oceanside.


September 21,  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 22 to September 24,  in Key Largo
Take Stock in Children Backcountry Challenge
This annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. Fishing is allowed around the clock from Friday night through Sunday afternoon. A popular weekend auction showcase and Sunday evening dinner are open to the public. Proceeds support local vocational scholarships for all ages and Take Stock in Children scholarships for financially challenged Upper Keys students.


September 24,  in Big Pine
Sheriff's Animal Farm Open House
Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located at 5525 College Rd. on Stock Island at the Sheriff's Office Headquarters complex. The family-friendly Sheriff's Animal Farm is open 1 - 3 p.m the second and fourth Sundays of the month.


September 24,  in Islamorada
Mangroves & Mimosas
Join Surfrider Foundation for a morning mangrove cleanup at 10:30 a.m. followed by celebratory drinks for purchase at Robbie's beach bar at 12:30 p.m. Bring your own paddleboard or kayak or rent one for free from Robbies, located at MM 77.5 bayside.


September 24,  in Key Largo
Dolphins Plus Marine Mammal Responder Open House
Visit Dolphins Plus Marine Mammal Responder's free open house from 10 a.m. to 2 p.m. for activities, demonstrations, tours, kids activities, food trucks and more. There will also be a birthday celebration for dolphin "Tug," who is turning seven years old. The organization provides a home for dolphins that can't be released to the wild, and is also the only whale and dolphin stranding organization in the Florida Keys. 31 Corrine Place.


September 28,  in Key Largo
John Pennekamp Coral Reef State Park: REEF Fish ID Talk
Representatives from REEF Environmental Education Foundation present a Fish ID talk at 11 a.m. in the Visitor Center auditorium. Learn how to identify the many species of fish you can spot while snorkeling the reefs within John Pennekamp Coral Reef State Park. Free with regular park admission. Mile marker 102.5 oceanside.


September 29 to September 30,  in Marathon
Sword Fest
Warriors on the Water and Two Conch Charters present the first annual Sword Fest tournament -- the ultimate swordfish battle. Cash payouts increase with the number of entry fees. With 30 boats, first place for heaviest swordfish pays $10,000. The tournament benefits Warriors on the Water, providing a positive outlet for veterans to enjoy nature and one-of-a-kind charter fishing experiences.


September 29 to September 30,  in Islamorada
Conch Scramble Charity Golf Tournament
Floating greens, golf boats and biodegradable fish food balls highlight the annual “par-tee” on the water. Fans of golf and boating can expect to have a “hole” lot of fun honing their swings and raising money for charity one shot at a time. Teams of four and a designated boat driver “caddy” make stops at nine Islamorada waterfront venues and come ashore to tee off. Each player has two shots at the floating holes using biodegradable golf balls that dissolve into fish food after 90 hours in the water. Both the Friday night kick-off party and Saturday tournament start take place at SD. Marine, 85500 Overseas Hwy. bayside.


September 30,  in Key Largo
ReMARCable Tour de Keys
The ReMARCable Tour de Keys is a 100-mile, one-day bicycle ride from Key Largo to Key West. Each rider is asked to raise $100 for the Monroe Association for ReMARCable Citizens, providing services for developmentally disabled adults. This event is not a race, but rather a charity "century" ride. The supported ride departs from the Holiday Inn at MM 100 in Key Largo at 7:00 a.m. with expected arrival at the Opal Key Resort in Key West at MM 0 at 3 p.m., with a party at the resort from 3 to 5 p.m. Pre- and post-ride hotel rooms and bicycle rentals are available to book for ride participants at special rates. Find more info and registration at marchouse.org


September 30,  in Key West
Key West Paddle Classic
The 26th 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.




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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