Cycling
(cycling.ky )
26 September: Reefathlon cycling event starting and finishing at the Reef Resort in East End. A selection of a 19, 38 or 57 mile ride is available, catering for all ability levels. For more information visit reefathlon.com.
 
17 October: Time trial championships. Contested over 10 miles down South Sound Road and back.

Swimming
(caymanactive.com )
11 September: Fosters Food Fair Sea Swim. A fun 800m sea swim along Seven Mile Beach.
Triathlon
(triathlon.ky)
28 November: Cayman Islands Triathlon. Olympic or sprint distance, as well as a 10k run.

Road running
(caymanislandsmarathon.com) 
11/18/25 September: Fidelity Fun Run series. Three two-mile races spread over three Saturdays. For more information visit caymanactive.com.
 
5 December: Cayman Islands Marathon. Featuring a full marathon, half marathon, as well as a team relay event, the Cayman Islands Marathon is a great event to train for.
 
As it only takes place in December, there is still more than enough time to get in shape.