A total of 16 of the world’s largest sailing yachts are scheduled to set off on the historic America’s Cup round the island course in the Rolex Race Around the Isle of Wight on Monday 13 June. The race, organised by the Royal Yacht Squadron in co-operation with the New York Yacht Club, is being run as part of the finish celebrations for the Rolex Transatlantic Challenge fleet, just as it was in 1997 for the Atlantic Challenge Cup presented by Rolex.

The 55-mile course, clockwise around the Isle of Wight, was used in the 100 Guineas Cup on 22 August 1851, when America, belonging to a syndicate led by New York Yacht Club Commodore John Cox Stevens, beat the best yachts the British sailing establishment could muster. In winning this race and taking the 27-inch tall trophy back to their New York club house, thus began a series of races known as the America’s Cup and a winning streak that would last until 1983.

A majority of the yachts competing in the Rolex Race Around the Isle of Wight will have competed in the Rolex Transatlantic Challenge, including race favourites Robert Miller’s 140ft (43m) schooner Mari-Cha IV and Charles Brown and Bill Buckley’s 100ft (30.5m) Maximus. Mike Slade’s Leopard, which holds the counter-clockwise race record for around the Isle of Wight, is another entry. However, there are several additions. The Grand Prix class is joined by Charles Dunstone’s 76ft (23.1m) Reichel Pugh maxi and 2003 Rolex Fastnet Race winner Enigma and American Mike Webb’s Breakaway. The Performance Cruising class will see additional entries from Hamilton, a Swan 86 also owned by Charles Dunstone, and Richard Matthews’s Oyster 74 (22.5m) Oystercatcher XXV.

This clockwise course was last raced during the America’s Cup Jubilee regatta in 2001 when the elapsed time winner was Stealth, the all-black maxi of the late Gianni Agnelli, in a time of 4 hours and 48 minutes–less than half the time it took America to sail the course.

The Rolex Race Around the Isle of Wight will start from the Royal Yacht Squadron line with a first warning signal at 0800 UTC (0900 local time).