How a sailing regatta (almost) put the wind in my sails

I don't mix well with water, but after experiencing Cowes Week I have begun to see the beauty of the boating life

A shot of the start of a race at Cowes Week (Getty)

If I won the lottery — an especially unlikely prospect in my case, as I never play it — I'd be susceptible to the lure of all the customary accoutrements of a lottery millionaire, the villa in the South of France, the sports car, the fancy holidays etc.

The one thing I'd wouldn't spend my money on is a boat. I've put sailing alongside shooting, fishing and horse riding as the pursuits I'll probably get through my life without mastering. I never felt I had the combination of practical, logistical and physical skills necessary to be a sailor, and I don't much like being on the water, which turns out to be something of a handicap, too.

On the very odd occasion that I've been invited on someone else's boat, I immediately felt a sense of claustrophobia: the idea that you can't get off exactly when you want was something I found particularly disconcerting. I can appreciate that bobbing about in the Aegean Sea at sunset, gin and tonic in hand, is a rather appealing prospect, but I feel it's possible to achieve pretty much the same effect on dry land.

Crashing through the vicious swell in the Solent at 30mph, hitting the waves like they were brick walls, the spray hitting my face like a freezing cold, salty shower, is quite another matter, and this was the way I spent part of my weekend. I was in a RIB (a rigid-hulled inflatable boat, for the uninitiated) commuting from Southampton to Cowes on the Isle of Wight.

Cowes Week, one of the world's most venerable regattas involving more than 1,000 boats of a variety of sizes, has managed perfectly well without me for 186 years, and it's unlikely that my observations will create much of a ripple at the Royal Yacht Squadron.

The most striking of my first impressions looking out to sea was that I couldn't make head nor tail of what was going on. It made a really impressive sight, but hundreds of boats of different classes taking part in different races at the same time was, to the untutored eye, little more than organised chaos. Passenger ferries and commercial boats weaved their way through the flotilla of yachts, adding to the general sense of disarray. It was the nautical equivalent of Hyde Park Corner.

I was extremely fortunate that my guide to what was going on was Shirley Robertson, the Olympic sailor and the only British woman to win gold medals at consecutive Games, in 2000 and 2004. Shirley is as patient as she is delightful, and she answered my pathetically naive questions - “What's a spinnaker?”, “How do you sail against the wind?”, Do they have the Internet on the Isle of Wight?“ - with forbearance and good humour.

And then, when she clambered on to a racing boat and delivered her instructions to the crew, dispensing individual responsibilities, I could see that here was a master practitioner at work. As the boat sailed away, gracefully slicing through the waves, and heading smoothly towards the setting sun, I understood, for the first time, the universal beauty of this esoteric sport. It was almost enough to make me revise my opinion of sailing. But not quite.