June 2025 Vacation Guide Marathon Florida - Best Things to Do
- Debbie Kronebusch
- Jun 3
- 6 min read
Updated: Jun 4
Bales Away at Grassy Flats Resort & Beach Club, Woman Up at Marathon Community Theater, Mosaics in Marathon, & the Father's Day Dolphin Derby
Welcome to your summer escape where turquoise waters glisten, friendly locals greet you like family, and every moment feels like a new adventure, Marathon, Florida is calling. This June, our slice of paradise in the heart of the Florida Keys is alive with sunshine, family-friendly events, and outdoor experiences perfect for all ages.
Looking to explore? Spend the morning kayaking through the mangroves at Curry Hammock State Park, where nature and serenity go hand in hand. Visit the Crane Point Hammock & Nature Center for shaded trails and a glimpse of Old Florida history. If you're traveling with kids, the Children’s Rotary Park is a perfect pit stop to burn off energy in the ocean breeze. And for a little retail therapy, swing by Shady Palm Art Gallery & Photography to browse unique coastal art and handcrafted gifts from local makers.
Whether you're here for the festivities or simply soaking up the laid-back Florida Keys lifestyle, Marathon in June delivers the perfect mix of relaxation, exploration, and lasting family memories.
June 4, 11, 18, 25
Marathon in June isn’t just about turquoise waters and tropical cocktails—it’s about soul-stirring moments, too. And if you’re looking to catch the heartbeat of the local culture, live music at Grassy Flats Resort & Beach Club is the perfect place to start.
One of their events this season is Bales Away—a celebration of the sea, the stories that sail across it, and the islanders who’ve carved their lives along the shoreline. Hosted on the breezy beachfront at Grassy Flats, this one-of-a-kind gathering blends music, storytelling, and the laid-back vibe the Middle Keys are famous for.
Justin Angelo brings a sound that feels like salt air and soul in every note. Influenced by John Mayer, Dave Matthews Band, and Jason Mraz, Angelo’s music is heartfelt and honest—perfect for those golden hour moments when the sun dips low and the Keys come alive with music and meaning.
His voice carries that familiar Jack Johnson ease, but his lyrics run deeper. With themes of mindfulness, humility, and connection, his songs speak to those looking for more than just a catchy tune—they invite you to slow down and be present. And really, what better soundtrack could there be for a Florida Keys beach vacation?
At Grassy Flats, you’re not just watching a performance—you’re part of something that feels intimate, authentic, and totally Keys. It’s the kind of evening that makes you grab the hand of someone you love, lean back in your chair, and think: This is exactly what we came here for.
June 6 & 7
When you're in the Florida Keys, adventure often takes center stage outdoors — but here in Marathon, creativity shines just as brightly indoors. Marathon Community Theater (MCT) is a beloved local gem that brings people together to celebrate the arts, tell stories, and—this month—dance their hearts out.
This June, MCT presents its Community Dance Showcase, an evening that celebrates the rhythm, talent, and spirit of the Middle Keys. You'll witness a dazzling variety of performances from the MCT Dance Department, local studios, community groups, and solo artists—each bringing their own style, flair, and passion to the stage.
Expect a wide range of dance numbers—from graceful contemporary and ballet to upbeat jazz and maybe even a bit of island flair. This is more than just a recital—it's a full-blown celebration of local talent and the power of movement to bring people together.
The show runs approximately 90 minutes, including a short intermission—just enough time to grab something from the concessions bar. Whether you’re in the mood for a champagne cocktail, a crisp glass of wine, or some sweet and savory snacks, you’ll find treats to enjoy as you take in the show.
This is the kind of night that feels special without being fussy. It’s the perfect way to experience a deeper layer of the Florida Keys community—where art and hospitality go hand in hand.
June 7
Looking for a fun, hands-on way to soak up the Florida Keys vibes? Come spend a sunny afternoon making your own coastal masterpiece at this laid-back mosaic art experience — perfect for guests ages 8 and up!
Choose from a whole lineup of island-inspired designs like an anchor, flamingo, sea turtle, mahi, mermaid, starfish, seahorse, and more. Whether you’re into margaritas or marine life, there’s a project waiting with your name on it.
Projects start at $40–$65 (plus tax + small registration fee), and all materials are included — just bring your imagination and a splash of Keys spirit.
And when creativity works up an appetite, pop over to Sparky’s Landing next door for food and drinks with a waterfront view. (Trust us, the fish tacos and frozen drinks are worth the visit.)
Whether you're a crafty pro or just in it for the fun, this is a great way to make memories — and something beautiful to take home, too.
June 13-14
Every June, the vibrant community of Marathon, Florida, comes alive with the spirit of camaraderie and competition during the Father's Day Dolphin Derby. Celebrating its 39th year in 2025, this cherished event offers families and fishing enthusiasts an opportunity to bond over the thrill of the catch and the beauty of the Florida Keys.
Scheduled for June 13–14, 2025, the derby kicks off with a Captain’s Meeting and final registration on Friday, June 13, from 9 a.m. to 6 p.m. at Two Conchs Bait & Tackle, located at 11499 Overseas Highway. The following day, anglers will cast their lines at 8 a.m., with the fishing window open until 3:30 p.m. Participants will then bring their catches to the weigh station at Two Conchs Marina between 4:00 and 5:30 p.m.
The day concludes with an awards banquet at 6 p.m. at Florida Keys Aquarium Encounters, celebrating the day's achievements and fostering a sense of community among particpants.
The derby offers substantial rewards for standout catches:
1st Place: $4,000
2nd Place: $2,000
3rd Place: $1,000
4th Place: $500
Additionally, the Junior Division (for anglers aged 15 and under) recognizes young talent with rod and reel combos valued at $200, $150, and $100 for first, second, and third places, respectively.
Beyond the competition, the Father's Day Dolphin Derby is a heartfelt tribute to the bonds between fathers and their families. It provides a platform for creating lasting memories, teaching younger generations about the joys of fishing, and appreciating the natural beauty of the Florida Keys.
Where Laid-Back Luxury Meets the Best of the Florida Keys
Marathon in June is pure summer magic. Long, sun-drenched days meet cool ocean breezes, and every moment invites you to slow down, dive in, and truly connect—with the sea, with your family, and with yourself.
Whether you’re chasing adventure or craving relaxation, our June vacation guide for Marathon Florida delivers. You’ll find family-friendly activities, local events, and those peaceful island pockets where time seems to stretch just a little longer. From boating and beach picnics to fresh-caught seafood and breezy sunset strolls, there’s no shortage of unforgettable things to do in Marathon FL this month.
So if you're dreaming of the perfect Florida Keys summer vacation, or already tucking those flip-flops into your suitcase, we’re ready when you are. Marathon is the heart of the Keys—and once you’re here, it has a way of staying with you.
Come for the experiences. Stay for the togetherness. And let the Keys work their magic.
Whether you're casting a line in the Father’s Day Dolphin Derby, tapping your toes to live tunes at Grassy Flats, clapping along at the Community Dance Showcase, or getting crafty with a colorful mosaic workshop, June in Marathon is all about making memories with the people you love.
And when the day winds down, there’s no better place to land than Casa Feliz — your private beachfront escape where luxury meets laid-back living. Thoughtfully designed for multi-generational families, it’s a space where everyone can unwind in their own way, whether that's poolside under the palms or with a nightcap by the sea.
Looking forward to welcoming you soon.
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