Your Guide to Top Florida Keys Activities - May 2025 Things to Do in Marathon
- Debbie Kronebusch
- May 4
- 5 min read
The Siegel at Marathon Community Theater, Mother's Day Dolphin Tournament, Drag Queen Bingo, & The Keys 100 Ultra Marathon
If you're dreaming of a spring getaway where the ocean sparkles, the community welcomes you with open arms, and every day offers a new adventure, Marathon, Florida is your perfect destination. This May, our island town is brimming with events and activities that celebrate the unique spirit of the Florida Keys.
Beyond the events, Marathon offers a plethora of attractions to explore. Visit the Turtle Hospital for an educational tour, relax on the sandy shores of Sombrero Beach, or take a scenic walk across the historic Old Seven Mile Bridge to Pigeon Key. For marine life enthusiasts, the Florida Keys Aquarium Encounters provides interactive experiences with local sea creatures.
Whether you're here to participate in the festivities or simply soak in the laid-back island vibes, Marathon in May promises a blend of excitement, relaxation, and unforgettable memories.
May 8-24
Looking for a delightful night out while you're here in the Keys? Don’t miss a performance at Marathon Community Theatre, our small-town gem with big-time heart. This month, they’re bringing The Siegel to life on stage—a sharp, witty romantic comedy about love, timing, and the sometimes-messy business of moving on.
The story follows Ethan Siegel, a hopeless romantic who unexpectedly shows up at his ex-girlfriend’s house with a bold question: will she marry him? The only hiccup? She’s already with someone else. What unfolds is a funny, thought-provoking ride through modern relationships and second chances.
With its intimate setting and passionate local cast, catching a show at MCT feels like being part of the community—even if it’s your first visit. It’s a perfect low-key evening for those who love great storytelling, a few laughs, and a cozy, cultural slice of Keys life.
Performances run throughout the month—grab your tickets early, they do sell out!
May 9-10
If you're looking for something memorable (and just a little thrilling) to do this Mother's Day weekend, the 19th Annual Mother’s Day Dolphin Tournament in Marathon is a local favorite—and for good reason.
Held May 9–10, this tournament isn’t just about fishing; it’s about community, giving back, and making lasting memories on the water. Anglers of all ages and experience levels are welcome, with divisions for Pro, Weekend Warrior, Lady, and Junior anglers. Whether Grandma’s holding the rod or the grandkids are cheering from the boat, it’s the kind of event that brings generations together.
Proceeds go to Habitat for Humanity of the Middle Keys, so every fish you reel in helps reel in support for affordable housing right here in the Keys.
Here’s the reel deal:
Captain’s Meeting: Friday, May 9, 6–7 PM at The Island Fish Company
Fishing Day: Saturday, May 10
Lines in: 7:30 AM
Lines out: 3:30 PM
Weigh-in: 3:30–6 PM at Marathon Yacht Club
Awards Banquet: 7–9 PM at the Yacht Club
Entry Fees range from $85 (Junior) to $200 (Pro/Weekend Warrior), and every penny raised helps local families find safe, affordable housing.
So if you're spending Mother’s Day here at Casa Feliz or anywhere in the Middle Keys, this is a fantastic
way to get out on the water and give back—all while chasing that prize-winning mahi.
May 11
If you're in the Keys this Mother's Day weekend and craving something fabulously fun, Drag Queen Bingo at Marathon Community Theatre is the place to be! On Sunday, May 11, from 5 PM to 7 PM, join the inimitable JJ Mills for an evening brimming with laughter, sass, and a touch of glam.
This month's theme is "Happy Mother's Day!", so feel free to don your most dazzling attire—costumes are welcome but not required. Doors and concessions open at 4 PM, offering a variety of snacks and drinks to keep you energized for the evening's festivities.
Tickets are just $12, and with limited seating available, it's wise to secure yours early. This event is for guests 18 and over, ensuring a night of mature humor and unbridled fun.
Whether you're a local or just visiting, Drag Queen Bingo at MCT promises an unforgettable experience filled with joy, community spirit, and a whole lot of fabulousness.
May 17
If you're visiting the Keys in mid-May, don’t be surprised if you see determined runners powering down U.S. 1 with support crews in tow—it's all part of the Keys 100 Ultra Marathon, happening May 17, 2025. This isn’t just any race; it’s a bucket-list challenge through some of the most scenic stretches of the Florida Keys, and it’s just as inspiring to watch as it is to run.
Whether you’re cheering on a friend or just love the buzz of a good competition, this weekend-long event is a great excuse to explore the islands at a slower pace (with a coffee or mimosa in hand).
🗺️ Where to Catch the Action
Key Largo to Key West: Runners in the 100-mile individual and team relay start bright and early in Key Largo and pass through each major island—including Marathon—before finishing at Higgs Beach in Key West.
Marathon Start Line: The 50-mile race and team relay kick off in Marathon at 9:00 AM on May 17. This is a great spot to catch the energy of a start line while soaking up some sunshine.
Big Pine Key: The 50K race begins here at noon, and runners hit their stride as they enter the home stretch toward Key West.
Key West Finish Line: Higgs Beach becomes a celebration zone as finishers arrive late Saturday into Sunday morning—many of them having run through the night. It’s emotional, triumphant, and definitely worth seeing.
💡 Pro tip: Bring a sign, a cowbell, or just your best cheering voice. These runners are out there for up to 32 hours, and your support really does make a difference.
So if you’re in town that weekend, don’t just watch the waves—watch people accomplish something extraordinary. Whether it's sunrise in Marathon or sunset in Key West, this race brings an unforgettable energy to the islands.
A Welcoming Place to Stay While You Experience Things To Do in Marathon Florida
Marathon in May is nothing short of magical. Our island town knows how to blend adventure with ease—offering moments that make you laugh, relax, and reconnect with the ones you love.
From family-friendly fun to unforgettable community events, there's something about May in the Middle Keys that just feels...right. Like the world slows down just enough for you to savor every salty breeze, every fresh catch, every joyful cheer from the sidelines.
So whether you're planning your visit with some of the many things to do in Marathon, Florida, or already packing your flip-flops—we can't wait to welcome you to the heart of the Keys. Here, memories aren’t just made. They’re made meaningful.
No matter what brings you to the Florida Keys—adventure, relaxation, or simply quality time with loved ones— when it’s time to unwind after a day of exploring, we invite you to a stay at Casa Feliz — a perfect blend of laid-back luxury and effortless hospitality. Make yourself at home in paradise. We’d love to welcome you soon!
Comments