Every day is an adventure in the Florida Keys, where the subtropical climate and scenic natural setting make an ideal backdrop for high-energy sporting activities all year round.
You can easily enjoy watersports and eco-excursions, unparalleled diving and offshore, inshore and flats fishing — no matter what the time of year. But the Keys also offer an energetic calendar of organized sporting events: marathons for runners, swim competitions, triathlons, cycling treks and much more.
For example, adrenaline enthusiasts can compete either on foot or on paddleboards in the Malibu Rum Hemingway 5k Sunset Run and Paddleboard Race set for Saturday, July 19.
It’s a highlight of the annual Hemingway Days festival, which celebrates the writing and exuberant outdoor lifestyle of the legendary author who spent the 1930s in Key West. You can test your strength in the 3-mile ocean paddleboard challenge, 5k run through historic Old Town — or even register for both!
And if you’re a paddleboard or self-propelled watercraft fan, Keys attractions also include the 12-mile Key West Paddleboard Classic. The race usually occurs in May, and the course takes you all the way around the United States’ southernmost island.
Have stamina to spare? Then consider competing in one of the Keys running events that test physical limits and personal resolve to the max. Chief among them is the KEYS100 Ultramarathon, also held in May, where U.S. and international contestants race 100 miles (yes, really!) from Key Largo to Key West.
Other Florida Keys running competitions include April’s Seven Mile Bridge Run across the longest segmental bridge in the world, and the Key Largo Bridge Run each November. And if you’re visiting Key West, enter the renowned Key West Half Marathon in January or the Southernmost Marathon & Half Marathon in October.
Besides running, the Florida Keys are home to swimming events that have inspired athletes for many years. They include the Florida Keys Community College Swim Around Key West, held each June, and Key Largo’s Orange Bowl Swimming Classic in January — a test of ability for the best collegiate swimmers in the U.S.
But that’s not all. If you enjoy mixing sports with history, check out Islamorada’s 8-mile Swim for Alligator Light. Generally scheduled for September, it helps raise awareness about the need to preserve the island chain’s aging lighthouses.
In addition, the Florida Keys host triathlons and cycling races that draw thousands of participants eager to vie for victory in multiple sports disciplines. If you’re one of them, start training for the annual Key West Triathlon. Held each December, it brings endurance-sports enthusiasts to compete in a fast-paced swim in ocean waters, bike ride and run along the Atlantic Ocean shoreline.
If cycling is your passion, the Keys also offer opportunities to enjoy biking vacations and tours. Among the most popular are the annual 200-mile BubbaFest Bike Tour, generally held in November, and the lively excursions hosted by Key Largo Bike and Adventure Tours.