13 Florida Half Marathons You'll Love Running
Big races, small races, road races and trail races, from Key West to Miami Beach, and from Cocoa Beach to Islamorada to Tampa — all updated for 2025
Key West Half Marathon
Key West, Fla. | Sunday, January 18, 2026
Fast, very flat and scenic throughout, the course for the race takes participants mostly around the edge of this, the easternmost island in the Florida Keys. It’s run during Key West’s coolest month of the year, when temperatures here average between the mid-60s and the low 70s, this race starts near the island’s ferry terminal and in its first mile take runners along world-famous Duval Street. Later stretches run past Higgs Beach and the southernmost point landmark, as well as past the Ernest Hemingway Home and Museum — home to perhaps the nation’s most interesting collection of six-toed cats (I’m not kidding).
The Donna Half Marathon
Neptune Beach, Fla. | Sunday, February 1, 2026
This is one of my favorite races, partly because it’s for a great cause — the goal of the Donna Foundation, which organizes the race, is to “finish breast cancer” — but also because it’s run through a beautiful part of coastal Florida, through neighborhoods just outside Jacksonville, including a two-mile run along the beach. It was founded by Donna Deegan, a well-known Jacksonville local television anchor who has completed several marathons after being diagnosed with breast cancer years ago — and is open to runners and walkers, with a generous 4 1/2-hour time limit.
Forgotten Florida Trail Run
Christmas, Fla. | Saturday, Feb. 1 - Sunday, February 1, 2026
A gorgeous, scenic, difficult and wild trail race through the Charles Bronson State Forest, Little Big Econ State Forest and Seminole Ranch just outside Orlando, where you’ll be able to choose from four distances: 8 miles, 15 miles, 50 miles and even 100 miles. Thanks to its location, you’ll run through and around plenty of palm trees, as well as through mud and water, and out in open meadows. As the race organizers describe it, these trails are a rare gem because the 15- and 50-milers are both single loops, with the 50-miler only repeating about a one-mile stretch. “While most races I’ve ever run are buffed out, this is more of a route than a trail,” the organizers say. “You’ll meander through massive palm growth one minute, and then be in wide-open prairie just seconds later.”
Seaside School Half Marathon
Seaside, Fla. | Sunday, February 16, 2025
Ever seen the Jim Carrey film The Truman Show? Then you have an idea of the kind of beautiful coastal architecture you’ll find along the route at this late winter race, which takes runners on a long out-and-back course along Highway 30A through several beach towns that stretch along Florida’s Gulf coast. The race is mostly flat and fast, and filled with ample views of the scenic Gulf waters and beaches, including Watercolor, Graytown Beach and Santa Rosa Beach.
Gasparilla Distance Classic
Tampa, Fla. | Sunday, February 22, 2026
Runners from around the country flock to the streets of this city that overlooks the waters of Tampa Bay in the late winter, both for the $10,000 in prize money its half marathon offers as well as the chance to record a PR, thanks to only a few turns and long stretches along flat roads near sea level. Most of the race unfolds along Tampa’s Bayshore Boulevard, which (as you might expect from its name) runs alongside the water; the other major stretch of the race is the big loop around Davis Island, just south of downtown.
305 Half Marathon
Miami Beach, Fla. | Sunday, March 1, 2026
You’ll start and finish this gorgeous run looking out onto the sand of Miami’s South Beach along its famed Ocean Drive, and from there run across two bridges, past the Miami Beach Golf Course and continue along Ocean Drive. The pair of bridges take you back and forth across Biscayne Bay, where you’ll take in the skyscrapers that tower over the intracoastal waterway, and then back again to South Beach, where you’ll run along roads lined with palm trees and past the historic art deco buildings the city is famous for.
Run Singer Island Half Marathon
Singer Island, Fla. | Saturday, March 28, 2026
Just down the shoreline from West Palm Beach, Singer Island — actually a peninsula, not an island — is known for its miles of beaches and beachfront hotels that tower over the ocean below. You’ll run long stretches along A1A, the scenic coastal highway that stretches all the way from Key West to the coast of Georgia, and inside John D. MacArthur Beach State Park, a barrier island nature preserve whose 348 acres protect endangered native tropical flora and provide nesting grounds for loggerhead, green and leatherback sea turtles. The race offers up a mix of nature trails through the park and stretches through the (much more) developed areas at the end of the peninsula, including a run across the bridge over the intracoastal waterway.
Dunes 50K Ultra + Heavy Half
Hobe Sound, Fla. | Saturday, April 26, 2025
A difficult yet beautifully scenic run along the soft sand trails and scrub forests of Jonathan Dickinson State Park, which at more than 11,000 acres is southeast Florida’s largest park. You’ll run from prairie wetlands near the start to the top of the dunes named the “dunes of Heaven” and the “dunes of Hell,” which promise to be an incredible test, especially thanks to the terrain — “endless rolling white sugar sand,” organizers say. You can choose from either the 50K or the half marathon, “through white sand dunes that will make you feel like you are going backward.”
Southernmost Half Marathon + 10K
Key West, Fla. | Sunday, October 12, 2025
Returning this year after a five-year break, this race will take you along the streets of Key West, Fla., where you’ll see the southernmost point in the U.S. — you can’t miss it, it’s marked by a red-and-yellow, bomb-shaped marker. Stretches of the race take you through the city’s Old Town neighborhood, where most of the tourist attractions and signature Key West-style architecture can be found, everything from restored wooden homes with lush tropical trees and plants growing outside to the Ernest Hemingway House, where the legendary author lived throughout most of the 1930s.
Trail Fest at Graham Swamp
Palm Coast, Fla. | Saturday, November 22, 2025
Natural trails made up mostly of soft sand and crushed shells — after all, you’ll be less than half a mile from the Atlantic Ocean — are what you’ll run at this race on the weekend before Thanksgiving. The race unfolds along the mountain biking trails inside Florida’s 3,000-acre Graham Swamp Conservation Area near Flagler Beach, about 2,700 acres of which are covered in swamps. You’ll run through a floodplain forest filled with bald cypress and sand pine trees, and as organizers say, “this trail is the most challenging trail in Flagler County, possibly even in Florida. There are lots of roots, rocks, steep descents and climbs, soft sand, quick switchbacks... you get the point. Take it all in, it’s incredibly beautiful too.”
Space Coast Marathon + Half Marathon
Cocoa, Fla. | Sunday, November 30, 2025
A race that unfolds entirely along the waters of the Indian River that flows between the cities of Cocoa and Cocoa Beach, this course is known for long, flat stretches shaded by the ever-present palm trees along the roads. You can choose between either the North or the South courses for your half marathon — either the first or the second half of the full marathon route. The north course has more hills, organizers say, plus “a great view of the NASA’s Vehicle Assembly Building just before the turnaround from across the river,” while the south course is the one to choose if you want to run “a more leisurely pace.”
Islamorada Half Marathon
Islamorada, Fla. | Sunday, December 14, 2025
You’ll run almost entirely along the Overseas Highway that stretches from the mainland of the Florida peninsula all the way to the end of the Keys at this race, which is all fast and flat thanks to its location just a few feet above sea level. While you can expect to encounter a few small bridges and a few detours onto roadside paths, the course will be pancake-flat nearly all of the way — and run through some of the most scenic stretches of these small islands.
Florida Holiday Distance Classic
Madeira Beach, Fla. | Sunday, December 21, 2025
You’ll run along the fast, flat shoreline of the Gulf of Mexico at this race, a point-to-point run from Madeira Beach all the way up to Taylor Park, along a course that mixes stretches along the beach with parts of Florida’s Pinellas Trail. Much of the course is run also through Seminole’s shaded public parks, especially the stretches along the Pinellas Trail, which offer a welcome respite from the bright Florida sunshine this time of year. Temperatures this time of year typically fall in the upper 50s around the starting time, and the race climbs only to about 70 feet above sea level at its highest point.
