What makes a boat cool? Yachting World has spent 100 issues asking the biggest names in sailing — Olympic champions, Volvo Ocean Race veterans, designers, navigators — to nominate their coolest yacht of all time, and the resulting top 100 reads like a love letter to the water, from tiny pram dinghies to 60-metre superyachts.
The online favourites say a lot about what floats people's boats. Windward Passage, the 73ft Alan Gurney design that sailors nicknamed a '73ft dinghy' on launch, was arguably the world's fastest yacht of its era and set a course record in the 1971 Transpac. The Cal40, meanwhile, gets the Mustang comparison: Stan Honey calls it the boat that changed offshore design forever, proving the fin keel and spade rudder combo in the mid-1960s — and still winning friends wherever it's moored. Topping the web votes is the Mumm 30, Bruce Farr's distilled one-design that gave 11 seasons of hard racing in the Tour de France à la Voile.
Then there's the nostalgia corner. Pro navigator Simon Fisher skipped the superyachts he's sailed and picked the International Cadet, Jack Holt's 10.5ft dinghy from 1947, where his passion was born. Others chose the Snipe, the Cherub and the 29er skiff. One nominee, Nikki Henderson, picked a boat she never sailed at all: Swallow from Swallows and Amazons, chosen purely for the childhood sense of adventure it represents.
At the other end of the scale, the superyacht picks are properly wild. Ngoni was commissioned with the brief 'build me a beast, don't build me a sheep in wolf's clothing' and became Ed Dubois's final design. Hetairos, the 60m Dykstra ketch, earns praise for fusing classic looks with cutting-edge hull engineering. And the J Class keeps its grip on the imagination — Peter Holmberg nominated the 2015-built Topaz for the way it blends 1930s lineage with modern technology.
Racing classes dominate too: the TP52, the Maxi 72, the bulletproof MOD70 trimarans that could cross an Atlantic then be hosed off and raced again, the record-breaking Volvo 70s, and the foiling IMOCA 60s now pushing offshore sailing to its limits. There's even room for the gloriously eccentric 42ft Kuka Light, a canting-keeled keelboat so extreme it makes the famous Comanche look conservative.
Why does this matter if you're not a racing sailor? Because boats are where sailing holidays begin. Charter a first boat, take a dinghy course, or simply daydream — this list is a masterclass in why people fall for sailing, and a reminder that today's hero boats started as someone's crazy idea. Skim it before your next flotilla trip and you'll have conversation material for every marina bar.
