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.
February
8th Annual Spanish Fly Music Festival
Ramrod Key Feb 1st
Get yourself down to Boondocks Grille and Drafthouse and help support the Jose Wejebe Foundation. They get support for their charitable endeavors, you get a day of music, sunshine, and cold drinks.
Cuda Bowl Fishing Tournament
Sugarloaf Key Feb 5th – 7th
Fish the shallows and bring up barracudas for fun and prizes!
Beats on the Bay – Touch and Go
Islamorada Feb 6th
Wear your favorite nu-wave outfit and rock to the sounds reminiscent of the Cars on the waterfront in Islamorada. Food and drinks sales help the Islamorada Community center fund scholarships for local young artists.
Key West Home Tours
Key West February 13th – 14th
Key West homes can be beautiful from the outside, and the Old Island Restoration Foundation gives you a chance to see them on the inside. Wander around the inside of 5 different homes a month from December to March. Just be respectable and don’t open the cabinets please.
President’s Day Cookout
Key West Feb 16th
Is there any better way to spend President’s Day than a cookout at the Little White House in Key West? Wear your red, white, and blue and enjoy a grilled burger.
20th Annual Florida Keys Seafood Festival
Key West Feb 14th – 15th
Did somebody say fresh seafood, music, activities, and crafts? I sure did! Head over to the Truman Waterfront Park for the weekend. Bonus: your admission gets you into a raffle for $250 worth of seafood. Don’t forget to save room for the Key Lime Pie.
Key West Art and Craft Festival
Key West Feb 21st – 22nd
Key West’s largest outdoor art show is at the Truman Waterfront Park. You won’t want to miss your chance to pick up nautical inspired crafts for your home, among other things.
17th Annual Sombrero Beach Run 5K/10K/15/
Marathon Feb 28th
Probably the best beach run ever! And it ends with a post-race celebration so be sure to bring your favorite lounge chair.
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March
Key West Orchid Festival
Key West March 6th – 8th
Key West Garden Club hosts this yearly event at the West Martello Tower. Stop on by to see local Florida vendors and learn all you need to know about Orchids.
Conch Honk
Key West March 7th
Limber up your lungs and lips for this conch shell blowing contest. Held at the Oldest House Museum & Gardens on Duval Street. Food, cocktails, and entertainment will be available. Conch blowing is free, food and drinks are not.
Beats on the Bay – Bay Jam 31
Islamorada March 7th
Live music from top local and national musicians on the waterfront in Islamorada. Food and drinks sales help the Islamorada Community center fund scholarships for local young artists.
Merch Merkin Fly Fishing Tournament
Key West March 9th – 12th
The largest catch and release permit tournament IN THE WORLD! Sign up and test your skill with anglers of all levels. If fishing isn’t your thing, go for the silent auction and help support conservation in the Keys.
Key West Home Tours
Key West March 13th – 14th
Key West homes can be beautiful from the outside, and the Old Island Restoration Foundation gives you a chance to see them on the inside. Wander around the inside of 5 different homes a month from December to March. Just be respectable and don’t open the cabinets please.
St Paddy’s Island 5K/10K
Islamorada March 15th
What a better way to get your body into shape before you blow it out on St Paddy’s Day. After your done with your run, be sure to hit the Florida Keys Brewing Company for the after party. First beer and a SWAG bag are available for the participants.
The Original Marathon Seafood Festival
Marathon March 14th – 15th
Help support local continuing education and scholarship programs while you get your fill of seafood. Don’t overfill because you’ll want to do some of the fun activities there. Plus! Live music, it just doesn’t get any better than this, unless…
Key Largo Seafood Festival
Key Largo March 21st – 22nd
Not to be outdone by Marathon, the Key Largo Seafood Festival features seafood, arts and crafts, live music, and BOATS! That’s not all, Saturday is also the Beer and Wine Festival (see below). PSA: bring your beach chair.
Key Largo Beer & Wine Festival
Key Largo March 21st
Enjoy your seafood and then get your craft beer attitude going at the Beer and Wine Festival. Unlimited samples of over 100 beer, wine, and spirits, now you can look down on those Miller Light drinkers in style.
Taste of Key West
Key West March 23rd
Sample dishes from over 40 Key West restaurants. There are three ways to enjoy, General Admission, Two for Taste Pass, or go all out and spring for the VIP experience.
Key West Sailfish Tournament
Key West March 26th – 28th
How can you top fishing for sailfish, prizes, and parties? You can’t. Don’t miss out on Key West’s best sailfish tournament, get your crew together and sign up now!
Island Fest
Islamorada March 28th – 29th
Arts and crafts, music, car show, home-made boat races, and a hula hoop contest! It doesn’t get any better than this! All at the beautiful Founders Park in Islamorada. This is Keys living!
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April
Spanish Fly Shark Tournament
Key West April 2nd – 4th
Get your team together and reel in that record size shark plus get featured on TV! You can’t lose; you’ll already be in Key West.
Ninth Annual Easter Egg Roll
Key West April 4th
Two! Easter egg hunts, plus get your pic with the Easter Bunny Himself. Get yourself and family down to the Truman Little Whitehouse and enjoy arts and crafts, live music, and refreshments. Plus the kids get a commemorative wooden Easter Egg!
Bets For Pets
Key Largo April 4th
Break out your polyester shirt and dust off those platform shoes and head on over to the disco themed Casino Fundraiser to help support Marrvelous Pet Rescue. Open bar, $2,500 in gambling tokens, and maybe even a pet adoption is waiting for you.
Afro Roots Fest
Key West April 3rd – 5th
Live music, cultural performances, and fantastic food round out this weekend event.
7 Mile Bridge Run
Marathon April 11th
You’ve driven over it, now run over it. Join the Marathoner’s Runners Club and experience the 7 Mile Bridge like you never have before.
Key Largo Anglers Club Offshore Tournament
Key Largo April 11th – 12th
Fishing in paradise and getting prizes? What’s not to like?
Key Largo Anglers Club Flats Tournament
Key Largo April 16th – 18th
Fishing in paradise and getting prizes? What’s not to like?
Marathon Premier Sailfish Tournament
Marathon April 16th – 18th
You can’t be the fishing capital of the world and not have a sailfish tournament that also helps underprivileged kids. Sigh up today and help make a difference. The awards banquet makes it all worthwhile.
Marathon Premier Sailfish Tournament
Marathon April 16th – 18th
You can’t be the fishing capital of the world and not have a sailfish tournament that also helps underprivileged kids. Sigh up today and help make a difference. The awards banquet makes it all worthwhile.
Beats on the Bay – Crossfire Creek
Islamorada April 17th
Don your favorite cowboy hat and boots and experience country music on the waterfront in Islamorada. Food and drinks sales help the Islamorada Community center fund scholarships for local young artists.
Dead Fest Key West
Key West April 17th – 19th
Don’t forget the Alamo’s Key West Dead Fest. Live bands paying tribute to the Grateful Dead all weekend long.
Conch Republic 44th Independence Celebration
Key West April 17th – 26th
Plan your vacation around this one! A whole week of parties, galas, balls, boat races and a lot more.
Florida Keys Lionfish Derby and Art Festival
Key Largo April 22nd – 26th
Lionfish, the invasive species that everybody loves to hate, and eat. Family friendly activities, lionfish tasting, and conservation information.
Foreigner at Coffee Butler Amphitheater
Key West April 23rd
Lou Gramm sings all the Foreigner hits for one night and Coffee Butler Amphitheater. It feels like the first time you’ll want to urgently get your tickets now to see these juke box heroes. They’re just waiting for a girl/guy like you to attend.
Key West Songwriters Festival
Key West April 29th – May 3rd
Catch a rising country star at the Key West Songwriters Festival. This festival has helped kick off the careers of notable stars Florida Georgia Line, Kacey Musgraves, Jake Owen and more. Show up for five days and night of fun!
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May
Nick Sheahan Dolphin Rodeo
Tavernier May 1st – May 3rd
Saddle up your favorite dolphin, wait, scratch that. Get your fishing gear together and join the competition to catch the biggest dolphin, maybe even win the $25K prize! Proceeds go to scholarships for Coral Shores High School students.
Marathon Bull and Cow Tournament
Tavernier May 1st – May 3rd
Three days of fishing with a guaranteed $20,000 first prize? Better get your boat in spring shape.
Happy Birthday Harry Truman
Key West May 8th
Celebrate Harry Truman’s birthday at the Little White House. Festivities and history on the front lawn.
Key West Paddle Classic
Key West May 9th
They’ve been racing paddleboards since 1997 for fun and prizes. You don’t have to race to participate in the silent auction. Cross off your racing bucket list with this race that starts at Higgs Pier.
Ladies Let’s Go Fishing, Screaming Reels
Islamorada May 15th – May 17th
Gather up the girls for a fun weekend of fishing, lessons, and parties! You don’t even need a boat; charters are part of the fee.
Golden Fly Tarpon Tournament
Islamorada May 18th – May 20th
Try to top world class anglers and top guides in this fishing tournament. Leaves from the Lorelei Restaurant with your chance to win custom art and gear.
Skippers Dolphin Tournament
Key Largo May 29th – May 31st
Fishing, dockside parties and awards, sounds like the perfect weekend. Sign up and get your gear ready.
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Don’t miss out on events and happenings when you’re in the Florida Keys!
June
Don Hawley Tarpon Fly Tournament
Islamorada June 1st – June 5th
Fish to become the Grand Champion! Get your name on the Perpetual Trophy of this fly tournament that has been going on since 1975.
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