When Major Cyril Windeler suggested to the Island Sailing Club that it should run a race round the Isle of Wight, it was to him an obvious opportunity for the owners of smaller yachts to enjoy a bigger than usual competition.

Major Cyril Windeler, founder of the RTI

This was the age of Big Boat racing and the beginning of the J Class, but the new race was restricted to vessels of between 5 and 25 tons. The course was challenging, but not too challenging and could be successfully completed in a day from the centre of British yachting – Cowes.

What began as a race for 25 starters in 1931 has grown and grown to a peak of over 1,800 competitors. For many sailors, the Round the Island Race is a once-a year, not-to-be-missed jolly on a summer’s day. For others it is a battle of wits over a complex course, involving changing currents, unpredictable breezes and idiosyncratic tides.

There have been many changes over the years. It is taken for granted now that the race is sailed in a westabout direction, but the second race, in 1932, had the fleet of 32 starting to the east.

Threading the Needles

Until 1955, Bridge buoy had to be left to port and then there were years in which it was possible to ‘thread The Needles’, passing between two of the chalk pillars. Jack Knights did so with great success in a Yachting World Diamond to win the race in 1961, but the practice was frowned upon and from 1963 until 1980 Palm buoy was dropped offshore of the infamous hazards, Goose Rock and the wreck of the Varvassi.

When the entry was extended to boats of more than 25 tons in 1948, the bigger boats raced for the Crankshaw Bowl and had to round the Nab Tower. That practice was dropped after one year. The start line was also the finish line until 1980 when a separate finish was set between Prince Consort buoy and a committee boat to the north – three years later the double finishing line, as used today, was established.

Round the Island facts

First raced 1931

Biggest fleet 1,875 in 2008

Distance 50 nautical miles

Startline Royal Yacht Squadron line, Cowes

Finish Off Prince Consort, Cowes

Last winner of Gold Roman Bowl Contessa 26 High Potential, Ross Applebey

Course record 2h 22m 23s MOD70 Concise 10 Ned Collier-Wakefield (2017)

Fastest monohull 3h 43m 50s Mike Slade, 2013, ICAP Leopard

Most wins Sir Edward Heath, 4, in a succession of Morning Clouds

Yachts are in view the whole way round from vantage points on the Isle of Wight and from Hurst Point and Gilkicker on the mainland

For many years there was no time limit for the race – that changed in 1975 – and nowadays there is no shortened course facility. The reasoning behind this is that there is such a wide range in the boats’ speeds that a call for a shortened course would have to be made within three hours of the start, by which time some of the slower boats might still be in the west Solent and the fastest in the east Solent.

Ghosting along to windward in 1932. The 8-metre Felise leads from Guenora, Cutty Sark and Farewell

And it is at the eastern entrance to the Solent that there have been recent changes. The clearance of the obstruction between No Man’s Land Fort and the Island shore allowed boats inside the Fort, which was, until 2005, a mark of the course, but the practice was actively discouraged.

The critics complain that it gives an added advantage to the smaller boats, but ever since the first race when Peter Brett’s 22ft Cornish fishing boat won on handicap, half the races have been won by boats of less than 30ft LOA.

The pattern changed in the Sixties after a couple of victories by modified folkboats, with the introduction of one-tonners. There were two wins in succession for Sir Max Aitken’s Roundabout and then in the Seventies came the Admiral’s Cuppers, led for three years in a row by Sir Edward Heath’s Morning Clouds – in 1971 and 72 the 40ft Lallow-built S&S version and in 1973 the 45ft Morning Cloud III.

Former Prime Minister Sir Edward Heath sailing Morning Cloud IV to victory in 1980. Photo: Beken

The former Prime Minister claimed a fourth win – a record no one has bettered – in 1980 with the Ron Holland-designed 44ft Morning Cloud IV.

Dominating folkboats

However, folkboats do appear to have claimed the limelight, even if some are lightly disguised as Contessa 26s. Builder Jeremy Rogers and his family have scored three victories (only the second skipper to do so) with Rosina of Beaulieu, but it must be recorded that since Edward Donald’s win with Celia Mary in 1999, there have been seven victories for folkboats or their derivatives, making a total of 11, the earliest being H.B. Shaw’s Katrina in 1948.

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The exact nature of the error that led someone to share the wisdom of the ‘5Ps’ with me has grown…

Which does tend to point a finger towards the handicap systems used. When the race began, and until 1971, the RORC Rating and time scales, in seconds per mile, were used to determine the winner of the Gold Roman Bowl, the overall handicap prize.

Sir Max Aitkin’s S&S-designed Roundabout in 1971. She won the Gold Roman Bowl twice in the Sixties. Photo: Beken

After that it was the International Offshore Rule (IOR). An unrated class was introduced in 1977 and this quickly became popular, accounting for 761 of the then record entry of 1,813.

In 1984 the Channel Handicap System (CHS) was introduced and in 1999 the IRC which continues to be used to this day.

Notorious hazards

There are a number of notorious hazards to the race that have a nasty habit of fighting back. The list of those who have hit one or other of the obstructions off The Needles is almost endless, but happily there have been no life-threatening accidents. The ‘hairpin’ bend at this stage is tempting in the extreme, and there are Goose Rock and the wreck of SS Varvassi to avoid.

A press of spinnakers as the fleet rounds The Needles in 2006. Photo: Thierry Martinez

In 1990, Bruno Troublé hit the Varvassi wreck in the French Admiral’s Cupper Xeryus and so damaged the boat that it had to be abandoned and sank. Part of the stern was recovered and can still be seen in the Haven Bar in Lymington.

Three years later my Barracuda of Tarrant, with the current editor of this magazine in her crew, was forced too far west at this point and the starboard rudder hit the Varvassi’s boiler, bent the stock and forced the aft edge to pierce the hull. Donning lifejackets, the crew abandoned the boat as it was taken in tow.

Goose Rock has trapped a few too. In 1995, Mike Slade’s Longobarda hit the western end of it and came to a grinding halt. Chris Law, who was steering, went through the port steering wheel. Having warned the crew: “Brace yourselves,” I joined him and the owner through the starboard one.

Surprisingly, Spirit of the North, with vastly experienced Owen Parker in charge, must have seen our dilemma yet still piled onto the eastern end of the rock. Doubtless others will hit these hazards in the future.

Spirit of the North receiving assistance after hitting Goose Rock off The Needles in 1995. Photo: Jamie Lawson-Johnston/PPL

For the majority, the passage will be safe, and for some fast. In 1933, two boats took more than 24 hours to complete the course (there was no time limit until 1976), but when multihulls were allowed to enter in 1961, a new world opened. The race record had stood to the 12-metre Little Astra at 7h 45m since 1948, but Don Robertson’s 36ft catamaran Snow Goose reduced it to 6h 34m. Tony Bullimore in Apricot and Mike Whipp with Rodney Pattisson in Paragon reduced the time further and, in 2001, Francis Joyon, sailing with Pattisson in the 60ft trimaran Dexia Eure et Loire cut it to 3h 08m.

The monohulls got quicker too. In 2001 Mike Slade in Skandia Life Leopard claimed his third monohull record only to shatter it again in 2008 and 2013. Records come only when conditions are ideal – when the wind is due north, for example, and the tide turns in favour at The Needles and the flood is not too strong after Bembridge Ledge buoy.

Any boat entering the Round the Island Race follows in the footsteps of many famous boats. Chris Ratsey’s Evenlode, a Fife-designed 34-footer was twice best on corrected time. Franklin Woodroofe’s 36ft Nicholson design Lothian was a double winner, as was Sir Max Aitken’s S&S one-tonner Roundabout.

Photo: Thierry Martinez / Sea&Co

There have been many other level-raters at the front, including Robin Aisher, with his Yeoman XXV. And in 1988, Harold Cudmore steered the Whitbread maxi Drum for Arnold Clark to win the Gold Roman Bowl. There have been J Class yachts such as Velsheda and hordes of dayboats, Dragons, Etchells, Ultra 30s and South Coast One-Designs such as Marbella, which won the Silver-Gilt bowl in 2007. And there will be many more.

The mystery of the Gold Roman bowls

When Cyril Windeler’s idea for a race was still gestating within the Island Sailing Club, he set about finding a trophy. He spotted a recently recovered Roman drinking vessel in a London goldsmith’s window. This Thames-dredged cup suited Windeler’s style and he commissioned a copy to be made by Mappin & Webb.

The replica, as was the custom of the day, was fashioned in silver and gilded. It wasn’t quite what Windeler had wanted, but it was sufficient for the first race in 1931.

But a second Roman Bowl was commissioned (and hallmarked) in 1937 from S. Blanckensee & Son of Birmingham to be fashioned in gold. It is 112mm in diameter with a single handle of 46mm and stands 72mm above the wooden plinth (fashioned of oak from HMS Victory). It weighs 244g. Windeler also ordered three silver replicas, which bear the hallmark of Blanckensee, but in Chester.

A sporting gesture by Chris Ratsey, who had been declared the winner in 1938 with the Fife-designed Evenlode, but suggested that he might have fouled another competitor and withdrew, led to Windeler presenting him with a silver bowl he had commissioned.

That cup, which is now presented to the boat finishing 2nd on overall handicap, was presented on Ratsey’s death to the ISC and is joined today by another silver-gilt trophy, which goes to the overall winner on ISC handicap rating.

The mystery as to which trophy is which comes from 1984 when what is thought to be the original silver-gilt trophy, bearing a 1931/2 hallmark, was presented to the Royal Lymington YC by the estate of Lionel St Clair Byrne. Byrne had won this bowl in 1953 when Windeler decided it should be awarded as a keepsake to the winner in Coronation year.

Local folklore records that Byrne used the two bowls for cocktail snacks, but decided that the gold one was too valuable to sit on his mantelpiece and took it for safe deposit to the bank. When the time came to return it to the ISC, he discovered he had deposited the silver-gilt one and inadvertently kept the gold one on show in his home.

The silver-gilt one is now the Lionel Byrne Cup and is presented each year to the Royal Lymington YC member with the best performance.

But where is the original Roman bowl dredged from the Thames? Could it be in the Mansion House (the official residence of the Lord Mayor of London) or at the Goldsmiths’ Guild or in some dusty cabinet?