The month of May is here, which means a feast of food, fishing, art, music and even an ultra-marathon in the Florida Keys & Key West.
Top events and festivals come thick and fast this month. Here are just a few top happenings not to miss in May in the Florida Keys & Key West:
Key West Songwriters Festival
Until May 4 Learn the stories behind your favorite country and pop hits. There are 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. This eco-minded event rallies scuba divers and land lovers to clean up the Keys. Collect the most trash? You could score big. Celebrate the hard work at the festival on May 4 at Founders Park in Islamorada, offering live music, food, and family friendly fun. Learn more.
Studios of Key West: Isaac Valdes – The Way It Was
May 1–29 A glimpse of Old Key West through the eyes of local artist Isaac Valdes. His detailed wood carvings capture the quaint homes, tropical landscapes and that laid-back island life. 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 at Fort East Martello with free popcorn, and a food vendor lineup from lemonade to frozen treats. Learn more.
Third Thursday Art Walks May 15
Walk on White – Key West (6–9 p.m.): Down White Street for a cultural crawl full of local art, pop-up performances and 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 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 to win cash, support great causes and enjoy camaraderie at an array 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.
