Legendary boats

Saša Fegić shares his pick of the boats that shaped sailing history and transformed the sport

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The history of sailing is not just a story of wind and water - it is also a story of boats.

The sea has a way of separating the merely good from the truly legendary. Some boats are just tools-floating concoctions of glassfibre and wood-while others etch themselves into the soul of sailing, rewriting the rules and leaving wakes that never fade.

From humble trainers to ocean-conquering racers, these designs didn't just sail-they revolutionised sailing and inspired generations of sailors.

OPTIMIST

Where sailors are born

Every child's first sailboat: simple, cheap and legendary. Every sailor remembers their first love. For most, it was an Optimist, a blunt-nosed plywood pram that felt like a bathtub but sailed like a dream. It looks like a wooden box with a sail, and that's precisely the point.

Designed in 1947 by Clark Mills as a simple, affordable trainer for children, the Optimist has introduced more children to sailing than nearly any other boat. It became the gateway drug for generations of sailors. Its genius lies in its crude simplicity-three sheets of plywood, a single sail, no complications.

The story of the Optimist begins in Clearwater, Florida. A spirited group of boys was hurtling down neighbourhood hills in wooden soapbox racers. The local Optimist Club saw promise in their reckless speed and boundless courage.

The club asked Clark Mills to design a sailboat that any child could build, sail, and afford. Mills sketched out what looked like a carpenter's toolbox with a daggerboard, rudder, and a single sprit-rigged sail. He called it the Optimist Pram.

Mills built the prototype from cheap plywood and nailed-together planks. It was 7ft 9in long and 3ft 8in wide. Its sail, originally cut from bed sheets or surplus canvas, was as square as a postage stamp. But it floated. And it sailed.