Easter regatta sails into focus

The 50th Easter Regatta is just three weeks away. 

The annual Round the Island sailboat race takes place on Good Friday, April 18.  

This year the Cayman Islands Sailing Club is hoping to get every sailboat in Cayman out on the water to celebrate. The first Easter race was held on Easter Monday, March 20, 1965, off the Beach Club Colony and was organized and run by the Cayman Islands Hotel Association. Prize money was £12 for first place, £10 for second and £5 for third as catboats raced with Sunfish and an assortment of small boats. 

By 1980, the Round the Island race for cruisers had become the main focus of the Easter Regatta. There were five boats in the race with John Stafford’s Aries beating out Canac, Sea Gypsy, Caronade and Honey. 

The numbers competing grew each year until Hurricane Ivan saw the demise of many boats in the fleet. Since then, there has been a slow but steady increase in the number of cruisers out on the waters of North Sound. 

The race is run by the sailing club in partnership with Harbour House Marina. The start of the race is in North Sound, and the course takes boats out of the main channel and then east around the Island, ending on Seven Mile Beach. The following day there is a shorter race “back to the sound” to complete the circumnavigation. There is also a short race course for smaller boats which goes west out of the main channel to Seven Mile Beach. Performance Handicap Racing Fleet handicapping is applied to allow all different boats to compete against each other. 

This year, Harbour House is going all out to attract as many boats as possible to compete in the 50th regatta. All boats that take part in the Round the Island Race will be eligible for a haul out and power wash prior to the race, at half the normal cost. Prizes include special 50th anniversary trophies for the first three boats and also Gill jackets, shirts and gloves for the podium crews. There is also a consolation prize of a free bottom job for the last-place boat. All competitors will get anniversary T-Shirts, and there will be a post-race party on Seven Mile Beach. 

If you would like to enter for the race, contact Rick Caley at [email protected] 


Cruisers will be in focus on the sea.

Support local journalism. Subscribe to the all-access pass for the Cayman Compass.

Subscribe now