Events in the Florida Keys & Key West for May 2025

KEY WEST, Fla. (April 29, 2025) — Whether chasing sunsets, tarpon, or your next favorite song, the month of May in the Florida Keys & Key West is serving up an entree of events from music, to fishing tournaments, to art walks and even an ultra-marathon. Here are a few events to put on your calendar this May: 

 Key West Songwriters Festival 

April 30 – May 4 Love learning about the stories behind your favorite country and pop hits? This five-day festival is your jam. Picture 200+ of America’s top pop and country songwriters playing more than 50 intimate shows all over Key West, with seasoned Nashville veterans sharing stages with tomorrow’s superstars. It’s year 29 for this fan-favorite event, and it just keeps getting better. Learn more. 

 I.CARE’s 3^rd Annual Trash Derby & Festival 

May 1–4 Do good, feel good — and maybe win some prizes while you're at it? This eco-minded event rallies scuba divers and land lovers to clean up the Keys. Collect the most trash? You could score big. Then celebrate your hard work at the festival on May 4 at Founders Park in Islamorada, offering live music, local food, family friendly fun and good feels. Learn more. 

 Studios of Key West: Isaac Valdes – The Way It Was 

May 1–29 Get a glimpse of Old Key West through the eyes of local artist Isaac Valdes. His detailed wood carvings capture the soul of the island—quaint homes, tropical landscapes and that laid-back island life. Nostalgia never looked so cool. Learn more. 

 Can’t Miss Key West Theater Performances 

• Paula Poundstone (May 9) – The queen of observational comedy brings her sharp wit to Key West for a one-night-only performance. Tickets 
• Duane Betts and Palmetto Motel (May 15) – Southern rock royalty takes  the stage with a guitar-driven performance rooted in Allman Brothers Band legacy. Tickets 

 Key West Outdoor Movie Night 

May 9 Movie night under the stars? Yes, please. Head to Fort East Martello for a free flick, free popcorn, and a food vendor lineup that’s got you covered—from lemonade to frozen treats. Learn more. 

 Third Thursday Art Walks May 15 

• Walk on White – Key West (6–9 p.m.): Head down to White Street for a cultural crawl full of local art, pop-up performances and even some complimentary drinks. Learn more. 
• Morada Way Arts District – Islamorada (6–9 p.m.): Art, live tunes, great eats and cool island energy in one of the Keys’ most creative communities.  Learn more. 

 Keys 100 Ultramarathon 

May 17–18 Ready to test your limits? This one’s for you. The Keys 100 is a 100-mile run from Key Largo to Key West. Not quite ready to go the full distance? There’s a 50-mile and a 50k option, too. Best part is crossing the finish line on the sand at Higgs Beach. Learn more. 

 FISHING EVENTS 

Cast your lines for the chance to win cash, support great causes and enjoy camaraderie in tons of tournaments spanning the island chain.  

• Marathon Offshore Bull and Cow Dolphin Tournament (May 2-4): A guaranteed $18,000 in cash awaits the top anglers who catch the largest bull and cow dolphin fish combined, with many other prizes awarded. Learn more.  
• Nick Sheahan Dolphin Rodeo (May 2-5): Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits Coral Shores High School students. The event features cash prizes for the top three adult anglers with the heaviest dolphin fish. Learn more.   
• 19^th Annual Mother's Day Dolphin Tournament - Fish for a Cause (May 9-10): This annual "Fish for a Cause" event benefits Habitat for Humanity of the Middle Keys, awarding cash prizes for the heaviest mahi. Learn more.  
• Ladies Let’s Go Fishing Screamin’ Reels Tournament (May 16-18): Screamin’ Reels is a fun, non-intimidating tourney with two days of fishing in Islamorada. Each tournament participant gets about $20 in free gifts, a face protector, a coozie, and more. Learn more.  
• Golden Fly Invitational Tarpon Tournament (May 18-21): The first of the “big three” tarpon tournaments held each year in Islamorada during the famed tarpon migration, The Golden Fly attracts top fly anglers and world class guides. Learn more.  
• 11^th Annual Skippers Dolphin Tournament (May 30 – June 1): This highly competitive, family-friendly tournament features cash prizes of more than $50,000 including a first-place prize of $20,000. Learn more.  

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