From family-friendly 5Ks to the legendary 7 Mile Bridge Run and the extreme Keys Ultra 100, the Florida Keys are a runner’s paradise. Race season here is more than just miles, it’s about fitness travel, stunning scenery, and the island lifestyle. Whether you’re chasing a new PR or planning a fun running getaway with friends, there’s an event for every pace.
Here’s your month-by-month guide to the Florida Keys races for 2025–2026.
October 2025: Scenic Starts & Island Vibes
October 12 – Key West Southernmost Half Marathon/10K | Register Here
Kick off race season with a classic destination half marathon in Key West. With flat roads, ocean breezes, and island charm, it’s one of the most scenic races in the U.S.
October 20 – Fantasy Fest 5K (90’s Theme) | Register Here
Run, dance, and celebrate during Fantasy Fest. Key West’s biggest party of the year. Expect bold outfits, live music, and island fun at every turn!
November 2025: Family Runs & Holiday Traditions
November 15 – Islamorada Old Highway 5K | Register Here
A casual, family-friendly run through Islamorada’s historic Old Highway. Great for all ages and a perfect excuse to get moving in paradise.
November 27 – Southernmost Turkey Trot 5K & Rooster Romp (Key West) | Register Here
Swap the Turkey Trot through your neighborhood for one surrounded by roosters and island charm. Start Thanksgiving morning the Key West way! Fit, festive, and fun.
December 2025: Bridges, Beer Miles & Big Races
December 6 – Key Largo Bridge Run (5K/10K) | Register Here
For one day a year, the Jewfish Creek Bridge closes to traffic and opens to runners. With 360° water views, it’s one of the most breathtaking race experiences in the Florida Keys.
December 13–14 – Islamorada Half Marathon, 10K, 5K & Beach & Beer Mile | Register Here
A whole weekend of racing and celebrating. Push your endurance in the half marathon, or just kick back and laugh through the Beach & Beer Mile with your running crew.
December 14 – Key West Triathlon | Register Here
Swim, bike, and run in paradise. Athletes rave about the warm-water swim, the stunning coastal course, and the electric finish line energy. This isn’t just a race, it’s a world-class triathlon experience in a one-of-a-kind setting.
January 2026: New Year, New Goals
January 17–18 – Key West Half Marathon | Register Here
Recognized as one of the best winter half marathons in the U.S., this race combines a flat, fast course with unbeatable scenery. Perfect for kicking off the new year with strong strides and sunny skies.
February 2026: A Luxe Women’s Getaway
February 14 – Islamorada Women’s Only Half Marathon | Register Here Elegant. Empowering. Unforgettable. This women’s-only event blends high-end touches with Keys island charm, making it the ultimate running getaway for girlfriends or a Valentine’s weekend retreat.
April 2026: The Bucket-List Bridge
April 11 (Tentative) – 7 Mile Bridge Run (Marathon) | Register Here
Since 1982, the 7 Mile Bridge Run has been one of the most iconic events in Florida. Runners cross one of the longest bridges in the world, surrounded by nothing but turquoise water. It’s only 7 miles, but the challenge lies in both the run and the registration. Spots sell out in minutes! So when it comes to this race, the early bird gets the bib.
Travel Tip: Even if you don’t snag a spot, the Keys buzz with energy during this event, making it the perfect springtime visit.
May 2026: Endurance Redefined
May 16–17 – Keys Ultra 100 (Key Largo–Key West) | Register Here
A grueling 100-mile journey across the entire island chain. For ultra runners, this is the ultimate endurance test. A once-in-a-lifetime chance to push your limits surrounded by breathtaking scenery.
Run Hard. Rest Easy. Stay with Star Properties Destinations.
After your miles are logged, let the Florida Keys lifestyle take over. At Star Properties Destinations, our vacation rentals provide everything you need to recover and recharge:
● Spacious homes for stretching out sore legs.
● Pools and hot tubs for post-run recovery.
● Waterfront views for the ultimate cool-down.
● Prime locations near Key Largo, Islamorada, Marathon & Key West.
● Concierge services to elevate your recovery: post-run yoga, in-home massage, or even bike rentals to keep your legs moving.
Because here in the Keys, the finish line is only the beginning of your fitness escape. ️
🏝️ Run hard. Rest easy. Stay with Star Properties Destinations.
