Below is a list of events for you to check out when you’re in the Florida Keys.
The Florida Keys always have something going on, farmers markets, art walks, concerts, and more. We’ve compiled a list of monthly/semi-monthly events, to find out what’s going on when you’re here, click on the links below:
Key West Farmers Market every Thursday.
Art Walks – Islamorada – Key West
Sheriff’s Office Children’s Animal Farm
The History of Diving Museum always has special exhibits going on.
Key West Theater for concerts, comedy, and bingo.
Concerts, conversations, and cabaret at the Tennessee Williams Theatre.
Monday Night Jazz Jams at the American Legion Post in Key West.
Marine Lab Sunday Funday, the second Sunday of every month.
July
Key West Lime Festival
Key West July 1st – 5th
Where better to celebrate citrus than Key West! 5 days of pie eating contests, sip and stroll, hot wheel races, and pie tasting tours!
Pick a day and go, or go for all five days and get your fill of pie.
250th Anniversary of the Signing of the Declaration of Independence
Key West July 3rd
How can you celebrate Independence Day any better than on the lawn of the Little White House? Enjoy a free BBQ and pony up to the cash bar. Fun for the whole family!
Don’t forget to wear your red, white, and blue.
Celebrating Freedom 4th of July
Key Largo July 4th
Parades, picnics, and fireworks in the Keys, it just doesn’t get any better than that! Begin your day by making your way to Key Largo Community Park and either watch or participate in the parade. After that enjoy a community festival and picnic. End your day enjoying fireworks.
Islamorada 4th of July Celebration
Islamorada July 4th
Food trucks, face painting, music, and a puppy parade lead to a spectacular fireworks display at Founders Park. Bring your chairs and blankets but leave your coolers at home there will be beer, rum punch, soda and water available.
Key West Rotary 4th of July Fireworks
Key West July 4th
After you’ve had your fill of hamburgers and hot dogs, head on out to the Edward B. Knight Pier, for more hamburgers and hot dogs, music, and fireworks!
Poor Boys Tarpon Fly Tournament
Islamorada July 4th – July 6th
Any tournament that starts at Lorelei is bound to be fantastic! Sharpen those hooks and swab those decks and get ready to fish. After hours, enjoy the lively clientele of Lorelei’s!
Rotary Club of Key West 5K
Key West July 4th
Lace up those shoes and hit the streets of Key West for this 5K that supports the Edward B. Knight Vocational Scholarship Fund.
Afterwards you can proudly wear your SWAG race t-shirt to the fireworks show.
Underwater Music Festival
Lower Keys July 10th – July 11th
It’s a party. Underwater. Don your favorite underwater costume and hitch a ride to Looe Key for this unique weekend of fun.
No word on whether the Little Mermaid and her entourage have RSVP’d yet.
Del Brown Invitational Fly-Fishing Tournament
Lower Keys July 12th – July 15th
Invite only rookies. This is the longest running permit tournament in the world. Get your boats ready and hope for an invitation.
Hemingway Days
Key West July 19th – July 26th
Hemingway look-alike contest, running of the bulls, interesting stories, and fellow fans are in Key West to celebrate the life of famous author Ernest Hemingway.
Key West Marlin Tournament
Key West July 22nd – July 25th
World class sportfishing and cash prizes! After your day on the water stay for the nightly festivities. Go ahead, get your boat ready and sign up now!
Hemingway 5K Sunset Run
Key West July 25th
Run or walk a 5k in Key West and then get to go to an afterparty on the beach? Yes Please! You won’t want to miss this one.
Beach and Beer Mile
Key West July 26th
One mile, four beers, are you up to it? Prizes and fun are all the rage for this event. Maybe you’ll win the prize for the least dressed if you plan your wardrobe right or ditch the wardrobe all together.
Florida Lobster Mini Season
Florida Keys July 29th – 30th
You have two days to catch spiny lobster and have the freshest lobster that you’ve ever had. Snorkel or dive and have the time of your life, please limit your haul to 6 per person.
Please follow all Florida Fish & Wildlife regulations, licensing requirements, and boating safety guidelines before heading out on the water.
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August
Key West Lobsterfest
Key West August 5th – August 9th
Celebrate the opening of lobster season the way it deserves to be celebrated. With pool parties, pub crawls, street fairs, and trivia!
Proceeds go to the Key West High School Scholarship fund.
Tropical Heat 2026
Key West August 12th – August 16th
Five days of all male fun, sorry ladies. Sizzling pool parties, clothing optional events, and adult-oriented entertainment.
Key West Rum Fest
Key West August 12th – August 16th
You don’t have to be a rummy to have fun at this fest. Day trips, pool parties, sunset sails, and live music round out this fun weekend.
Key Largo Triathlon
Key Largo August 16th
After you’ve soaked up all that rum, head on up to Key Largo and run it off at the Key Largo Triathlon. Multiple events allow you to triathlon your way. Don’t forget to attend the post-race party.
The Big Splash
Key Largo August 22nd
Bring the kids to Key Largo for a fun day of waterslides, a foam pit, and bouncing fun! Kids only on the attractions please.
Key West Brewfest
Key West August 28th – September 1st
Calling all hipsters, 5 days of craft beer tasting culminating with the battle of the best beard boss. Just kidding, 5 days of beer tasting and fun ends with the Grand Tasting event at The Southernmost Beach Resort.
Key West Brewfest
Key West August 28th – September 1st
Calling all hipsters, 5 days of craft beer tasting culminating with the battle of the best beard boss. Just kidding, 5 days of beer tasting and fun ends with the Grand Tasting event at The Southernmost Beach Resort.
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September
Just a Few Friends Festival
Key West September 3rd – September 7th
Five days of live music celebrating the legacy of Jimmy Buffet. Grab your favorite luau shirt and flip flops and get to Key West to join other parrot heads and celebrate the tropical lifestyle that Jimmy lived and loved.
Key West Open Water Swims
Key West September 5th – September 6th
Swim 800 yards, 1 mile, or 2 miles in the beautiful waters of Key West. Or click the “Do it All” button and swim all three. Just get to Smathers Beach an participate.
Parrots and Margaritas 5K Run/Walk
Key West September 5th
Start your Labor Day right with a free margarita and glass. Just sign up for the race, I don’t even think that you have to actually run in it. Or go for the Flip Flop Mile and get to the post race celebration faster.
Swim For Alligator Lighthouse
Islamorada September 10th – September 12th
“One of the eight toughest swim challenges in the world”. If that doesn’t get your adrenaline pumping, check your pulse. An eight-mile swim in open water around the Alligator Lighthouse.
It’s named for the lighthouse, so you don’t have to worry about alligators while you swim, now sharks on the other hand…
Son Del Mundo Hispanic Heritage Celebration
Islamorada September 12th – September 13th
Come and celebrate Hispanic heritage with vibrant music, lively dancing, and delicious foods. Hosted at the Florida Keys Brewing Company in Islamorada Florida.
Grassy Key Paddle Battle
Marathon September 17th – September 21st
Sharpen up your paddle and prepare for battle at Grassy Flats Beach Club and Resort. Multiple events and categories, winners share in the pot!
Take Stock in Children Backcountry Challenge
Marathon September 25th – September 27th
Sign up and fish to help support this powerful mentorship program for Florida students. Scholarships academically promising, economically disadvantaged youth end up with a 95% graduation rate.
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Current events of festivals, concerts, fishing tournaments, and other happenings in the Florida Keys straight to your inbox.
October
Fall Backcountry Fly Championship
Islamorada October 2nd – October 3rd
Get your flies tied and your tackle sorted for this redfish and snook tournament. Multiple awards categories, if you play your cards right you can be King of the Backcountry.
Key West OktobBREWfest
Key West October 3rd
60 beer vendors, more than 225 types of beer, and live music? Where do I sign up? At the Southernmost Beach Resort of course.
Pro Tip – Sign up for the VIP tickets and get a commemorative poster and a special stainless steel VIP mug.
America 250 Florida Keys: 7 Mile Bridge Sunset Celebration
Marathon October 10th
Is there a better place to celebrate the 250th of the U.S. than the 7-mile bridge? Food and live music to help you enjoy the sunset.
Reef Fest
Key Largo October 12th – October 18th
Gather with other ocean lovers at Reef Fest. Seminars, snorkeling, and diving will dominate the weekend. You won’t want to miss the happy hour social! Don’t forget to participate in the silent auction.
Fantasy Fest
Key West October 16th – October 25th
Let the debauchery begin! Balls, parties, parades, spectacular body painting, and much more! The theme this year is Musical Icons and Iconic Musicals so start getting your costume ready now.
Casting for Cats Backcountry Tournament
Islamorada October 16th – October 17th
One-day ladies fishing tournament that raises money to help spay/neuter feral cats. New this year, co-ed and junior divisions.
Ladies Let’s Go Fishing
Islamorada October 16th – October 18th
Ladies, up your angling game this weekend with seminars and guided fishing expeditions. Be sure to participate in the Fishing Fever Tournament and win your prize.
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Current events of festivals, concerts, fishing tournaments, and other happenings in the Florida Keys straight to your inbox.
November
Coming Soon
December
Working on it.
January
This is all the way in next year, cool your heels.
February
Hell, if January wasn’t done, you didn’t really think that February would be done, did you?
