Registration is open for the 18th Annual race across the islands of the Florida Keys--May 16-17, 2026. This chain of unique and inter-connected islands--some inhabited, some not--end in the City of Key West, just 90 miles from Cuba. This is a pavement race, with approximately 75% run on paved bike paths or sidewalks and the balance on the road shoulder facing traffic. The Florida Keys, known locally as "The Conch Republic", is a spectacular and laid-back sub-tropical paradise, surrounded by the turquoise waters of the Atlantic Ocean and Florida Bay/Gulf of Mexico. The Keys feature great fishing, kayaking, snorkeling and diving, hotels, resorts, B&B's and cuisine and cocktails to fit every budget. There is entertainment to fit every taste, important history and a unique culture, sunsets that will keep you spellbound, special events going on throughout the year including KEYS100 , of course, and you don't need a passport to visit here! So, what are you waiting for? We've saved a space fo
Hotels Near This Race
Find accommodation close to the start line in Key West, FL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
RaceHotelFinder earns a small commission when you book through links on this page, at no extra cost to you. Results are sorted by distance from the race venue.
Race weekend dates pre-loaded on Booking.com. RaceHotelFinder may earn a commission at no extra cost to you.
Race Travel Insurance
Don't forget travel insurance for May 16.
You've trained for months and booked a trip to Key West, FL.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
