FLORIDA KEYS (June 5, 2025) —This Father’s Day Weekend, swap neckties and grilling gear for flip-flops and fresh-caught seafood in the heart of The Florida Keys. The centerpiece this year is the I Love Stock Island Festival, a five-day celebration packed with authentic island culture, vibrant community spirit and can’t-miss events perfect for the whole family – especially Dad.
From June 11-15, 2025, Stock Island rolls out the welcome mat with an unforgettable lineup of events steeped in local flavor and flair. This year’s festival invites visitors and locals alike to slow down, soak up the sun and experience the best of Stock Island’s culinary creativity, artistic soul and waterfront charm.
Highlights Include:
- Cayo Hueso Brewing Low Country Shrimp Boil (June 11): Kick off the festival at Cayo Hueso with cold craft brews and a bubbling shrimp boil in a real brew kettle. This deliciously laid-back feast sells out fast – so snag your spot early!
- Stock Island Food Truck Tour: Get your foodie fix all weekend long with a self-guided tour of Stock Island’s tastiest food trucks. No tickets needed – just follow your cravings and the interactive map to some seriously good local eats.
- Mural Art & Local Culture: Take the Stock Island Mural Art Tour, discover street art gems and snap Insta-worthy shots with the iconic 2025 I Love Stock Island Festival sign. Dive deeper into island lore on the Stock Island History Tour or join the Stock Island Collaborative Clean Up to help keep paradise pristine.
- Sip & Savor Experiences: Enjoy wine tastings and chef-crafted bites at An Evening with Winebow(June 12), ride the Taste of Stock Island Trolley Tour (June 13), or treat Dad to Bourbon, Beef & BBQ Dinners at Matt’s Stock Island Kitchen all weekend long.
- VFW Father’s Day Fishing Tournament (June 14-15): Set sail with Dad and cast a line for a cause during the 13th Annual VFW Fishing Tournament, where proceeds support local veterans. Register here.
- Father’s Day Brunch & Bonding: Whether it’s Father-Son Haircuts at Beards and Brews or a waterfront brunch at Matt’s Stock Island Kitchen (June 14-15), Stock Island is serving up quality time with the dads who matter most.
- Family Festival (June 14): Head to Bernstein Park from 4-8 p.m. for the I Love Stock Island Family Festival. From artisan markets, food, games, raffles, and music, it’s the ultimate community celebration with a purpose. Proceeds benefit the SOS Foundation and Food Pantry.
- Festival Closeout Bash (June 15): Wrap up the weekend with the Perry Marina & Bad Boy Taqueria’s Pool Party, featuring good vibes, tasty tacos and cool community fun.
Check out the full schedule of events and get more info at ilovestockisland.org.
Father’s Day Fun Across the Florida Keys
Father’s Day Dolphin Derby
June 13-14
Perfect for father-child bonding on the water, this two-day fishing tournament targets dolphin (mahi-mahi) and includes special divisions for kids 15 and under, who can win rod and reel combos and other great prizes. It’s a family-friendly event that combines the thrill of offshore fishing with a laid-back Keys vibe. Learn more.
College of the Florida Keys Swim Around Key West
June 14
This open-water endurance event challenges swimmers to complete a 12.5-mile loop around the island of Key West, taking competitors past mangrove islands, under bridges and through some of the clearest water in the Florida Keys. Participants can swim solo or as part of a relay team. Shorter races are also available for those looking for a less intense experience. Learn more.
Hot Rods and Dad Bods Car Show at Boondocks Grille and Draft House
June 15
This brand-new Father’s Day tradition in the Lower Keys features a classic car show hosted in partnership with the FL Keys Southernmost Car Club. Families will enjoy live music by StormFront, ice-cold drinks, raffle giveaways, a silent auction and activities for all ages. Whether you’re showcasing your vintage vehicle or just taking in the chrome and horsepower, it’s a day of cool cars and even cooler vibes. Learn more.
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