Events in the Florida Keys & Key West for May 2025 Celebrate Music, Marine Life & Reel Good Times
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 3rd 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.
- 19th 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.
- 11th 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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Did someone say jam-session? Gable Bradley and Joey Hyde show the crowd how it’s done during the kickoff concert for the 29th Annual Key West Songwriters Festival in Key West, Fla., on April 30, 2025. FOR EDITORIAL USE ONLY (Mark Hedden/Florida Keys News Bureau)
Music fans got a double dose of satisfaction with this brilliant backdrop at the 29th Annual Key West Songwriters Festival kickoff concert. Hundreds of fans swayed to the music written by emerging artists on Ocean Key’s Sunset Pier in Key West, Fla., on April 30, 2025. FOR EDITORIAL USE ONLY (Mark Hedden/Florida Keys News Bureau)
Two participants from last year’s Keys 100 Ultramarathon cross the iconic Bahia Honda Bridge along the Overseas Highway in the Florida Keys. The 100-mile race spans from Key Largo to Key West. FOR EDITORIAL USE ONLY (Tuan Nguyen/Florida Keys News Bureau)
Several participants from last year’s Keys 100 Ultramarathon run along the Overseas Highway just outside Marathon, Florida. The 100-mile race stretches from Key Largo to Key West through the heart of the Florida Keys. FOR EDITORIAL USE ONLY (Tuan Nguyen/Florida Keys News Bureau)
A diver cleans up debris during a guided I.CARE Coral Restoration Dive, which took place Friday, May 3, 2024. During the annual dives, participants help transplant coral and gain a deeper understanding of the critical role these reefs play in the health of the local marine ecosystem. FOR EDITORIAL USE ONLY (Frazier Nivens/Florida Keys News Bureau)
ABOUT THE FLORIDA KEYS & KEY WEST
The Florida Keys & Key West is a premier getaway destination located at the southernmost tip of Florida and the continental United States. The Keys stretch over 125 miles connected by 42 bridges and bordered by the Atlantic Ocean and the Gulf. Discover the spectacular array of diverse activities offered in the Florida Keys like fishing, diving, natural wonders, fine dining and cultural heritage. From large resorts, secluded waterfront hideaways and courtyard guest houses, visitors can uncover the perfect place for their vacation. Restoration, renovation and preservation have become a way of life in the Florida Keys. Whether you’re driving or flying into the Keys, one thing is for sure: there’s simply no place quite like it. Want more reasons to visit The Florida Keys & Key West? Get inspired at visitfloridakeys.com and follow us @thefloridakeys on social media.
MEDIA CONTACTS
Mary B. Haban
Senior Director of Public Relations
Visit Florida Keys & Key West
(305) 394-3142
Visit Florida Keys & Key West PR Agency Team (TURNER)