The annual Round the Island Sailboat race takes place on Good Friday, April 18th. This year marks the 50th anniversary of the Easter Regatta and we are hoping that we get every sailboat in Cayman out on the water to celebrate.

The first Easter Regatta was held on Easter Monday, 20th March 1965, off the Beach Club Colony, organised and run by the Cayman Islands Hotel Association. Prize money was £12 for first place, £10 for second and £5 for third and 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 5 boats in the race with John Staffords “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 we have seen a slow but steady increase in the number of Cruisers out on the waters of North Sound.

The race is run by the Cayman Islands 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 eastaways 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 westaways out of the main channel to SMB. PHRF handicapping is applied to allow all different boats to compete against each other.

This year Harbour House are going over the top to attract as many boats as possible to compete in the 50th Regatta. All boats who 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 for the last place boat of a free bottom job. All competitors will get an 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]