The definitive top 100 coolest boats of all time

What are the Coolest yachts of all time? Some of the greatest names in sailing choose the most iconic boats ever built

How do you define ‘cool’? It’s an unquantifiable quality. What’s cool to one person, might be banal or brash to another. But when it comes to boats, like people, some just have it. That vibe. That authenticity. That swagger. That je ne sais quoi. That undeniable cool factor.

Over the years we have asked some of the most successful sailors, designers and other leading lights in our sport to choose their ‘Coolest Yacht of all Time’. For 100 issues they have featured on the back page of Yachting World, from dinghies to dhows. With a century of nominations to consider, we’re trying to answer that unanswerable question: what makes a yacht cool?

When we ask for a ‘Coolest Yacht’ nomination, it’s a pretty open brief: sailors can choose any boat that inspired or excited them, or they found memorable or iconic. It can be the boat they most loved sailing, a boat they wish they’d sailed, or made a formative impact on their sailing career. Our only stipulations are that it is, ideally, not a boat that has been chosen before, but – as you’ll see from the list – some have been popular choices.

We also request pro sailors don’t automatically choose their current campaign, though a few have made it onto the list by dint of being, well, pretty darn cool. Otherwise, the choice is theirs.

So, what are the coolest boats ever? And which gets your vote?

WINDWARD PASSAGE can be considered the first modern Maxi. Photo: Oli Tennent/Getty

Pure brilliance

If ‘cool’ can be decided by the popular vote, then the most-read nominations here on yachtingworld.com offer three stand-out contenders.

Luca Bassani, the visionary founder of Wally Yachts, nominated Windward Passage. “For a long time she was the fastest boat in real time in the SORC regattas – ie the world’s fastest boat – and she can be considered the first modern maxi yacht.”

Designed by Alan Gurney as an ocean record breaker, Windward Passage’s semi-planing hull was beamy with a shallow canoe body, fin keel and an elegant run aft to a broad transom – a shape described on launching as a ‘73ft dinghy’. Successes included a race win and course record for the 1971 Transpac Race.

“A true yet forgotten myth,” concludes Bassani.

Navigator and innovator Stan Honey voted for the Cal40. The cruiser-racer has iconic status in the United States, famed for its downwind surfing performance. With its flat-bottomed hull and separate rudder and keel, “The Cal40 revolutionised yacht design,” says Honey.

“All ocean racers that came after had the fin keel and spade rudder that the Cal40 proved in the mid-1960s.

CAL40 Famed for its downwind surfing performance. Photo: Betsy Senescu/ultimatesailing.com

“The Cal40 remains competitive in racing and an easy-to-sail, well-mannered cruising boat, perfect for a couple,” he adds. “One aspect of owning a Cal40 is that everywhere you go folks come by the boat and tell stories about how they love the boat.

“It’s like driving a 1965 Mustang, everybody has fond memories. The Cal40 changed the design of offshore sailboats, like the ‘65 Mustang changed the design of cars, forever.”

Our single most popular nomination online is the Mumm 30. “I picked the Mumm 30 partly out of respect for Bruce Farr,” says designer Mark Mills. “The Mumm 30 for me is the most distilled essence of the clean, light, simple philosophy. It was drawn to be fast, easy to build, and straightforward to sail.”

MUMM 30 A clean, light and simple Bruce Farr design. Photo: Gilles Martin-Raget

Anyone who has sailed a Mumm 30 will know it could test you, thrill you, and get you very wet. “It went well in all conditions but perhaps its finest achievement was 11 years of the Tour de France à la Voile, where the variety of conditions and distances challenged many of the world’s best sailors in one of its best boats,” adds Mills.

INTERNATIONAL CADET Cultivates champion sailors. Photo: TimHampton.uk

Childhood heroes

It’s perhaps not surprising that for many sailors, their all-time favourite boat is their first boat. The simplest, smallest designs have launched great careers.

“I’ve been lucky enough to sail on a good selection of the ‘coolest’ yachts and I remember the excitement of the first time sailing each of them as I’m something of a fan boy when it comes to cool boats,” explained pro navigator Simon ‘Si Fi’ Fisher. “The MOD70, VO70, Comanche or a foiling IMOCA rightfully hold a place on this list, as do the TP52, IACC class and J-Class.

“So I’m going to the other end of the spectrum and nominating a junior class that gave me so much joy growing up. The International Cadet dinghy isn’t fast by modern standards or very technologically advanced but it was the boat that really cultivated my passion for sailing, whether racing at the weekends or tinkering on the driveway after school.” Jack Holt’s pram dinghy design dates from 1947 and is just 10½ft long.

CHERUB Grassroots sailing fun – fast, fiddly and unique. Photo: Suellen Hurling

Fisher is not the only Ocean Race and J-Class sailor to pick a traditional dinghy – Bouwe Bekking chose the 15ft, 1931-designed Snipe, which he sails with his family.

Emma Sanderson (née Richards) chose the Cherub. A popular ‘project boat’, Cherubs are fast, fiddly, and unique. The New Zealand fleet features parent-and-teen combos, including legendary sailors like Ray Davies and Dean Barker. “The Cherub has definitely rekindled grassroots sailing fun,” she says.

Hannah Diamond fell back in love with the sport when introduced to skiff sailing. “When I moved out of Oppies… I lost the love completely.” An afternoon trying a 29er changed everything.

Such formative memories don’t even have to be of a boat you physically sailed. “The story of Swallows and Amazons gripped me as a child,” Nikki Henderson recalls. “Like people, I believe boats have an aura, or a personality. To me, Swallow [represents]: adventure, freedom, and an innocent childlike curiosity.”

BALTIC 130 MY SONG A racer built for cruising in great comfort. Photo: Studio Borlenghi/ALeA

Superyacht icons

The superyacht world is where imagination can run riot, and has produced some truly innovative designs. Vasco Vascotto nominated the ketch Wallygator II (now Nariida) – the first all-carbon big boat, designed by Luca Brenta and Luca Bassani. “I remember an iconic picture of it reaching along at 25 knots… at an IOR time when the maximum speed was around 10 knots, so this was another level!” Vascotto says.

For photographer Gilles Martin-Raget, it’s the radical lines of the Wally 143 Esense, while superyacht designer Malcolm McKeon’s pick is the classic beauty of Alejandra, a 135-footer commissioned for King Juan Carlos of Spain.

HETAIROS A fusion of traditional looks and superyacht modernity. Photo: YPS Peter Neumann/Panamax

The Dykstra-designed 60m/218ft ketch Hetairos is ocean racer Mike Golding’s nomination: “Hetairos is a wonderful fusion of traditional looks and state of the art hull design and construction. Superyachts are seldom cool, in my view, but Hetairos is an exception. I’m full of admiration for owners willing to engage in projects of this scale: the yacht is a technical masterpiece.”

The Baltic 130 My Song got navigator Nacho Postigo’s vote (before the 40m racer-cruiser was sadly destroyed during a shipping incident). “What I love is the fact that somebody has been brave and said ‘OK, I want to go cruising, I want to have comfort, but let’s make sure this boat is fast’,” he explained.

NGONI The final, and possibly best, design by the late Ed Dubois. Photo: Breed Media

Perhaps the boldest of concept is Ngoni, Shirley Roberston’s nomination. The owner’s brief was famously to ‘Build me a beast. Don’t build me a sheep in wolf’s clothing.’ Ngoni was designer Ed Dubois’s final yacht before he died in 2016. “In so many ways Ngoni pushed Dubois and the builders, Royal Huisman, more than ever before,” says Robertson. “But I can’t help but think Ed saved the best to last.”

J CLASS RAINBOW For superlative superyachts, the J Class is hard to beat. Photo: Sailing Energy

However, when it comes to superlative superyachts, it’s hard to surpass the J Class. From the timeless elegance of Velsheda to the perfectionism of Svea or the irreverent smiley-face-hulled Ranger, all are iconic. Champion match racer Peter Holmberg nominated the 2015-built Topaz: “I love what we are able to do [with the Js], to sail to a high level, combining history with modern technology. Figuring out how to manoeuvre this thing properly, accurately, and do it right, is the ultimate challenge.”

Big boat favourites

Pro racing sailors are spoilt for choice, yet some classes have come up time and time again. One is the TP52 – Ian Walker voted for Patches five years ago, and his reasons still hold true. “The class has stood the test of time – the reason for its longevity and popularity, I think, is that it’s a perfect size and an absolute blast to sail.”

The Maxi 72 is another fleet with multiple votes. Mike ‘Moose’ Sanderson explains: “The Maxi 72 is the biggest boat where you feel you’re doing things properly. They don’t have a canting keel or daggerboards but are incredibly fast, beautiful to sail – right in the sweet spot – and potent under IRC because they are so refined.

MOD70 PHAEDO3 Built for the rigours of round the world racing. Photo: Carlo Borlenghi/Rolex Fastnet Race

One of the most popular nominations has been the MOD70. British ocean racer Brian Thompson says: “I’d choose the MOD70 without too much doubt because the boat is so beautifully thought out.

“They were born from the ORMA 60s development class. The best people of the ORMAs decided to build a boat that could go round the world, but was stronger, and having that buffer meant it is bulletproof. You can absolutely hammer it across the Atlantic then hose it off and go sailing again!”

Sam Goodchild agreed: “We’d be racing against boats like Comanche, they’d have 20-something people on the rail and we had five, doing circles around them!”

The Volvo 70s are another class that make those who’ve sailed them around the world a bit misty-eyed. Stu Bannatyne nominated the record-breaking Ericsson 4, Annie Lush and Benjamin Schwartz picked Puma.

“If I had to narrow it down to one boat, it would have to be Camper, which I skippered in the 2011/12 Volvo Ocean Race,” explains Chris Nicholson.

VOLVO 70 A boat that can make even grown sailors go misty-eyed. Photo: Dave Kneale/Volvo Ocean Race

“I first raced in the Volvo Ocean Race at the end of the Volvo 60 era, and then it was a quantum leap to the new Volvo Open 70. It started out with boats breaking and sinking and destroying themselves – to where we ended up with Camper.

“The Volvo 70s were a real handful and we had some huge moments, but the thing was they just demanded the best people you can find on the planet, at the top of their game, and that was such a cool, cool group of people to be part of. Camper brought out the best in us.”

OPEN 60 KINGFISHER Tiller steered and strapped in for a bumpy ride. Photo: Nature Picture Library / Alamy

Rapid development

Other nominations track the development of ocean racing. Nick Moloney voted for the innovative Open 50, “I was blown away by the wide-beam Finot-Conq designs that began to push the parameters of form stability,” he recalls.

Will Oxley went for Offshore Challenges’ Open 60 Kingfisher. “This thing is tiller-steered and you’re strapped in. You’re getting water pouring down the deck, screaming along. I remember it being the most amazing sailing I’d ever done in my life.”

Nigel Musto chose Aquitaine Innovations. “One of those breakthrough boats that precipitated a step change in sailing. Yves Parlier was, and continues to be, one of the sport’s great innovators. Aquitaine was the first Open 60 to use deck spreaders, allowing a full-chord carbon wing mast.”

IMOCA 60 CHARAL Pushing the class rule boundaries. Photo: Damien Meyer

Now foiling IMOCAs have taken offshore racing to another level. “When you look at what the designers and engineers have put in place to get round IMOCA rules and balance on a single foil, I think that is something extraordinary,” said Conrad Humphreys when he nominated the IMOCA 60 Charal.

The Cookson 50 deservedly claims its place on this list, as yacht designer Matteo Polli explains: “It included plenty of innovation for the time, including a canting keel system [with trim tab] to maximise stability.” The Farr design won classic offshore races, including the Fastnet Race and Sydney Hobart.

Mitch Booth voted for another canting-keeled design, the 42ft Kuka Light: “The most extreme keelboat I have ever sailed!” Booth said. “Around 3,200kg with a beam of 4.6m and draught of 3.5m makes Comanche look very conservative by comparison!”

You can’t pick an offshore racer without considering the huge and diverse fleet of Class 40s. Yoann Richomme says: “the best sailing potential of any glassfibre-built boats: they are now incredible machines.”

MINI 6.50 Small but full of adventure. Photo: Pilpre Arnaud/La Boulangere Mini Transat

But perhaps the coolest of all is the – often wildly complex – Mini 6.50. Clarisse Cremer started her career racing a 21-footer in the 2017 Mini Transat. “I have so many wonderful memories on the boat. I could have done a Moitessier, and if someone had thrown me some water and food, I’d have kept on going forever. It was just so beautiful and such an adventure!”

CLUB MEDITERRANÉE Four-masts and 75m long, built for single-handing. Photo: James Andanson/Getty

Bonkers but brilliant

Some boats truly are like nothing else. Club Mediterranée fits that bill. The outlandish 246ft (75m) four-masted behemoth was built for French sailor Alain Colas to sail solo across the Atlantic in the 1976 OSTAR. To control nearly 1,000ft2 of sail area, it included developments that were marvels of their time – cameras to monitor the masts, hydraulic winches, and push-button controls at the helm.

HYDROPTÈRE Built to take the 50-knot record over 500m – which it did. Photo: Marcel Mochet

Another yacht that is utterly unique is Hydroptère. “I thought Hydroptère was the most incredible boat for a long time,” says Pip Hare. “It was the first flying boat we’d ever seen. It crossed oceans and also was going for the 50-knot record.” The 60ft foiler was the brainchild of skipper and project founder Alain Thébault, together with design studio VPLP. In 2009 it took the 500m speed sailing record to 52.8 knots.

Less known, but equally ground-breaking, is Williwaw. Nominated by designer Rob Humphreys the 31ft foil-borne plywood home-built trimaran was designed by ‘unsung hero’ Dave Keiper in the 1960s. “He cruised her for 20,000 miles in the Pacific. That’s right – 20,000 miles of fast, hydrofoil bluewater cruising nearly 50 years ago!”

ULTRA 30 The original spectator-friendly chaotic short course racer. Photo: Stephen Munday

Firmly in the little bit bonkers category are the Ultra 30, nine-man trapeze monster skiffs. “The Ultra 30s were way ahead of their time,” says Eddie Warden Owen. Ultra 30 racing was the original spectator-friendly sailing, with short-course, crash-and-burn style races broadcast on BBC Grandstand. The 30s were monstrously overpowered, with bowsprits up to 15ft long and over 500ft2 of sail area. “Even the best would capsize and at the end of a 20-minute race the crew would be completely exhausted. And we’d have three races a day.”

SUPERFOILER Hard to sail, but rewardingly fast when you got it right. Photo: Andrea Francolini

Their modern descendant is the similarly manic Superfoiler. “A three-person, fast foiling boat that could reach pretty much 40 knots, with electronic rake control,” recalls Luke Parkinson. “It was a boat like no other. It always kept you on your toes – really hard to sail, but very rewarding when you got it right.”

ARABIAN DHOW Crew weight and sandbags keep them upright. Photo: Karim Sahib

The over-canvassed Arabian dhows secured Bruno Dubois’s nomination. “They are totally unstable with a huge mainsail.” The keel-less designs move sandbags and water ballast plus their 11-man crew weight for trim.

IACC VERSION 5 A ‘perfect blend of technology and beauty’. Photo: Domenico Stinellis/AFP/Getty

America’s Cup contenders

As the sharpest point of bleeding edge design, the America’s Cup has attracted nominations from some of the world’s most successful racing sailors.

Australian Tom Slingsby recalls: “I was obsessed with the Version 5 America’s Cup boats back in the early 2000s, I used to sit and stare at the TV.” The IACC yachts were last used for the 32nd America’s Cup in Valencia in 2007, with 11 Challengers.

“For me, those things are just the perfect blend of technology and beauty.”

Dawn Riley nominated America True – her yacht for the 2000 Cup which had the first gender-balanced crew in the event’s history (the otherwise all-female 1995 Mighty Mary crew had a sole male tactician).

USA 17 A huge wing-sailed tri, requiring enormous bravery on the helm. Photo: Pascal Lauener/Reuters/Alamy

The 2010 Cup saw arguably two of the craziest designs ever in a Deed of Gift match. Round the world record breaker Thomas Coville suggests, “The big trimaran challenger, USA 17. When you saw the size of the wing and the size of Jimmy Spithill steering the boat, and flying on one hull, I think it was totally amazing! We should give a medal to the generation in San Francisco for creating so many new ideas and dynamics, but for me the first step of flying was when those guys arrived with a trimaran with wings.”

New Zealander Ray Davies nominated the AC72, the wingsail catamarans sailed in the 34th America’s Cup in San Francisco in 2013. “It was at the infancy of foiling and a very radical stage. It was a bit of a cowboy show doing it for the first time. Early in that campaign we were down on lakes, towing craft around and capsizing and nose diving, pitch poling and all sorts of things.”

Freddie Carr voted for the next iteration – the AC45F one design raced leading up into the America’s Cup in Bermuda. “It hit a real sweet spot in the sport where we were sailing foiling catamarans – but we still had ropes and winches. Everything was human-powered, but we were doing stadium racing.

“The top speed we did in one was 41 knots. We bore away to go from a reach to downwind, and we were all drop-hiking. We were hanging on a toe strap, doing 41 knots. It was ridiculous. And I’ve never felt more vulnerable in my life on a boat!”

AC75 INEOS BRITANNIA The most successful British AC boat in 90 years. Photo: Ricardo Pinto/America’s Cup

And of course, there’s INEOS Britannia – the best performance British Challenger in over 90 years. British Cup helm Dylan Fletcher nominates the AC75 saying: “Sailing RB3 was breathtaking. An incredible piece of engineering that is rewarding to sail, hugely technical, that requires finesse to maximise performance.”

VESTAS SAILROCKET 2 Simply the fastest boat in the world. Photo: Vestas SailRocket

Record breakers

Is there anything cooler than being the first or the fastest in the world? Record-breakers feature highly in our list.

And the coolest of them all? Perhaps the fastest boat in the world. “With no hesitation, my choice for the world’s coolest yacht is Vestas SailRocket 2,” says designer Pascal Conq. The asymmetric Vestas SailRocket 2, piloted by the Paul Larsen, is one of the most extraordinary pieces of yacht design ever created and set a world speed sailing record of 65.45 knots (peaking at 68) in 2013 – which has never come close to being bettered.

Few boats became household names quite like the 75ft B&Q/Castorama, as nominated by photographer Thierry Martinez, who captured Ellen MacArthur’s return as she set a solo non-stop around the world record of 71 days in 2005. The photos made headline news the world over.

B&Q/CASTORAMA Made history with Ellen MacArthur. Photo: Th.Martinez

That record has tumbled over the years to just 42 days, most recently set by François Gabart in 2017. Dee Caffari nominates Gabart’s Macif, a 100ft trimaran which set a record the foiling Ultims are yet to smash. “This is a boat only a handful of people have ever been aboard but it’s a boat all the cool kids would really love to sail!” laughs Caffari. “It’s very, very fast. Gabart set the 24-hour record of 851 miles on his own – and he is very cool himself!”

GITANA 17 Ultims are technically the peak of sailing at present. Photo: Eloi Stichelbaut/polaRYSE/Gitana SA.

Since the advent of the Ultims, the world-girdling Maxi Edmond de Rothschild Gitana 17 (now Actual 4) has been nominated several times. “The Ultims are the most technologically advanced and fastest boats that you can still go offshore with, at incredible speeds: 30 knots upwind! They are technically the peak of sailing at the moment,” says Ocean Race co-president Johan Salen.

It’s not just multihulls. Mari Cha III was the pick of Yachting World’s former editor Elaine Bunting. The 146ft (44.7m) Philippe Briand maxi ketch was fast, elegant and formidable on the race course, setting records that included a transatlantic outright time in 1999 of 8d 23h.

RAMBLER 88 Designed as a giant slayer… and does just that. Photo: Carlo Borlenghi

Rambler 88 was designed as a giant slayer. After the loss of his Rambler 100, owner George David asked designer Juan Kouyoumdjian to create a boat that was capable of taking on 100-footers. Rambler 88 has claimed line honours wins in many classic offshore races, but in 2016 they took on the ARC rally, setting a new course record of 8d 6h.

“Although the ARC is a cruising rally for ‘normal’ cruising boats, it adds to everyone’s excitement when the course record is beaten. Most boats complete the 2,700-mile crossing in around 18 to 21 days!” recalled World Cruising Club boss Paul Tetlow.

“The sense of how developments in race boats filter into cruising boat design felt very real.”

COMANCHE Built for just one thing – to break records. Photo: Stefano Gattini

But for true swagger it’s hard to better Comanche, the 100ft rocketship so beamy she was nicknamed the ‘aircraft carrier’.

“Owner Jim Clark had a vision of all speed/no compromise. He was dared by a couple of Australian 100-footer owners to come join the party. The first lesson is never dare a billionaire to do anything! The result was Comanche,” recalled Ken Read. “VPLP and Guillaume Verdier’s design group created something that blew away our loftiest expectations.

“Comanche was built to do one thing only: be first to finish and break records. And that she did. Comanche is a water-bound rocketship, a pleasure to sail, turns heads wherever she goes, and so much fun to be a part of.”

STAR Finding the right balance is a true art in this class. Photo: Tom Gruitt

Olympic heroes

For many Olympians the boat that carried their national flag is irreplaceable. Enricco Chieffi represented Italy in the Star in 1996. To him the Olympic keelboat is enduringly cool. “It’s a 100-year-old design and yet so modern in its way. The Star is a very unbalanced boat and to find the right balance is kind of an art. But when you find it, it’s like getting fine music from a piano.”

Vita Heathcote went to the 2024 Games in the 470 – an Olympic class since 1976. “Very complex and fine-tuned, there is no tweak the 470 hasn’t undergone!” she says.

49ER Demands great tactical skills. Photo: Clive Mason

Spanish sailor Iker Martinez took gold in 2004 in the 49er, plus silver in 2008 and 2012. For him the men’s skiff is the pinnacle of sailing. “You need to sail very well as a tactician. You need to be very good on the starts. And you need to have some balls when it’s windy!”

Francesca Clapcich voted for the 49erFX, having represented Italy in 2016, the first Games the women’s skiff was introduced.

TORNADO Once you get a taste of this boat there’s no way back!. Photo: Jeff Brass

Carolijn Brouwer represented Belgium at the 2008 Games, helming the Tornado catamaran. “The Tornado is a really cool boat. Once you get a taste for it, there is no way back!”

She sailed with crew Sébastien Godefroid, long before mixed Olympic crews were commonplace. “This showed that being a woman you can be very competitive in a mixed gender configuration – just like the great Paul Elvstrøm did sailing with his daughter,” Brouwer reflects.

INTERNATIONAL MOTH Started a foiling monohull revolution. Photo: Martina Orsini

Fast flight

The first ever ‘Coolest Yacht’ pick was the International Moth, nominated by Paul Larsen. The Moth class was where the foiling monohull revolution really gained traction some 20 years ago.

“A cool boat it stands on its own, and for what it has since inspired. This little foiler came to the skiff/cat party and smacked all the old cool kids down. Things change when that happens,” says Larsen.

WASZP Foiling one design gone global, with huge racing fleets. Photo: Down Under Sail

Foiling designs have come and gone since, but the one-design Waszp has gone global, with huge fleets at their world championships. Hattie Rogers says: “It’s just awesome coming off the line flying with 80 other boats.”

Another class that was a source of development pre- and post-foils is the C-Class catamaran. Helen Darvelid explains: “The boats were marvels of DIY, small-shed ingenuity and efficiency. They were ultra-rare and if you wanted one, you had to design and build it yourself. These elegant wonders showed the sailing world what wing sails could do. America’s Cup, SailGP and outright speed sailing owe the C-Class a big nod of respect.”

F50 Top speed of over 50 knots – but there’s more to it than that. Photo: Jon Buckle/SailGP

Nathan Outteridge picked the foiling F50 in 2021. “The headline top speeds of over 50 knots are impressive, but there is so much more to these incredible boats.”

RELIANCE Engineering feat designed on paper and built in a short time. Photo: Niday Picture Library/Alamy

Game changers

Ask a yacht designer for their coolest yacht of all time, and chances are they’ll come up with a boat from the history books that changed the course of sailing. And many of them were designed by the great Nathanael Herreshoff.

Andre Hoek’s pick is the 1903 America’s Cup winner Reliance.

“The yacht was, for its day, such an extreme design and engineering feat, without computers and all designed and built in a short time. Herreshoff was the master.

“Reliance measured over 200ft overall with just 90ft of waterline [the huge overhangs were to take advantage of the rating rule when heeled], it displaced 189 tons and had a sail area of 1,500m2 (16,000ft2)!”

WESTWARD A vast sail plan at the leading edge of technology. Photo: Beken of Cowes

Bill Tripp nominated Herreshoff’s 1910 schooner Westward, whose vast sail plan was “at the screaming edge of tech at the time,” while Juan Kouyoumdjian also chose one of ‘Capt Nat’s’ boats, the 38ft Dilemma. Designed for Herreshoff himself, Dilemma was the first boat to successfully carry a fin keel, made of steel with a lead bulb. Antoine Koch chose Herreshoff’s multihull Amaryllis “the first modern catamaran”.

Then there are the experimental foilers. “It has to be Monitor, of course! The father of all flying rockets!” says Michel Desjoyeaux, adding, “Today it’s very difficult to find pure innovation.” But Monitor was hydrofoiling in 1955.

MONITOR Truly innovative and foiling back in 1955. Photo: Courtesy of Mariners Museum USA

Or what of boats that were ocean racing game-changers? Guillaume Verdier says: “Mike Birch’s Olympus Photo, designed and built by Walter Greene, sits at the root of all modern multis. Mike and his boat began the legend of the Route du Rhum and made offshore racing so popular.” The 40ft yellow trimaran beat the 69ft monohull Kriter on the line in 1978, and the potential of multihulls for ocean racing was proven.

Next came the trimarans – Vincent Lauriot-Prévost nominates Biscuits Cantreau 2. “Formula 40 was a very simple rule for multihulls for offshore racing,” he explains. “The boat had to be 40ft long, about 40ft wide. The majority of the fleet were catamarans, but we started with a trimaran. We wanted a trimaran which sailed like a catamaran, flying a hull – that was something very new. She was faster than the catamaran fleet, and beat them all.”

SWAN 55 GALIANA Performance, comfort and seaworthiness. Photo: Tapio Lehtinen/OGR

Going the extra miles

Many nominations are there for the experience they gave, rather than speed or results. Jimmy Cornell nominated Duen, a 50ft traditional Norwegian fishing boat that had been converted for liveaboard sailing. “I cannot think of a better example of a happy cruising family than the crew of Duen. As Duen plodded her way around the world with time of absolutely no importance, other young people were welcomed aboard with open arms, fed and looked after.”

Jeremy Wyatt nominates the modest Beneteau First 25.7, “a real pocket cruiser that provides a lot in very little.”

Modern performance cruisers on the list include the Finot Conq-designed FC53 Nica, a water-ballasted swing keeler; and the Gunboat 66 catamaran.

It’s no surprise that much-loved S&S Swans have numerous nominations. Tracy Edwards picks the Swan 65, while Tapio Lehtinen nominates the Swan 55. “In my opinion the Swan 55 is the classiest and most beautiful design Nautor ever built. It offers exceptional performance combined with comfort and seaworthiness – Galiana will take me safely anywhere on the planet.”

In terms of punching above its size, the S&S 34 is hard to beat. Don McIntyre selects it as “an innovative all-time classic”, citing its many remarkable feats, including Morning Cloud winning the 1969 Sydney Hobart, Jon Saunders’s twice circumnavigating solo in Perie Banou and 15-year-old Jessica Watson’s solo round the world in Pink Lady.

FOLKBOAT Can go for a leisurely picnic sail, race, or cross oceans. Photo: Tim Wright

But the boat that most proves ‘it’s not the size of the dog in the fight, but the size of the fight in the dog’ is perhaps the Folkboat. “The humble Nordic Folkboat is so simple, so beautiful, and so versatile,” nominates Leo Goolden, who sailed the 25-footer solo transatlantic.

“It can be taken for a leisurely picnic sail, quickly transform into a finely-tuned class racer, or even set up for ocean voyaging – and will excel at all three, with minimal expense. What could possibly be cooler than that?”

ORMA 60 Paved the way for the foiling Ultim trimarans. Photo: Kos Picture Source/Getty

Cult status

Still not convinced one of these is the Coolest Yacht of All Time? There are yet more boats that have been nominated, and many that – surprisingly – have not.

Would we have the foiling Ultims without the knife-edge control of the ORMA 60 trimarans? Where would the America’s Cup have gone without Australia II, a cool combination of original thinking, chutzpah and racing smarts? Or where would offshore racing be without Dorade or Stormy Weather?

Volvo 70s have been repeatedly nominated, yet iconic Whitbread Ocean Race yachts such as Silk Cut and Steinlager are yet to be. Despite the number of top sailors who cut their teeth in the Optimist, nobody has voted for the junior class.

IMOCA 60 HUGO BOSS Gained celebrity status with skipper Alex Thomson. Photo: Lloyd Images

The 18ft Skiffs are still going strong, and anyone who’s seen an International 14 up-close recently will have done well not to stare. Alex Thomson’s keelwalk and other stunts elevated his Hugo Boss Open/IMOCA 60s to celebrity status, while the unshowy capabilities of the Contessa 32, and their many adventurous owners, has given it a cult-level cool…

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