Yachting World has pooled the knowledge of some of the world’s best sailors and marine industry gurus to choose the coolest, most influential and innovative yachts in the world.

What makes a cool yacht?

As with beauty, coolness is in the eye of the beholder. Our list of coolest yachts runs from superyachts, to high performance offshore racers and dinghies, through historic 17th century clippers.

Each yacht holds a special place in the heart of one of sailing’s biggest names. Reading about their favourites demonstrates it doesn’t need to be the latest bit of tech or multi-million-pound superyacht that can inspire a life on the sea.

Coolest superyachts

Superyachts might be the preserve of the rich and famous, but that does not always mean that the most expensive and most sought and coolest superyachts are necessarily brand new bits of high tech kit.

The J-Class – the yachts on which the America’s Cup was contested in the earthly 19th century – have long been the most desirable yachts on the face of the earth.

It is hardly surprising, then, that former world No 1 match racer Pete Holmberg chose the J-Class Topaz as his pick for worlds coolest yacht.

At the other end of the scale in terms of modernity, when we asked one of the world’s best yachting photographers to nominate a cool yacht, Gilles Martin-Raget selected Wally 142 Esense.

“Sailing this very sensitive monster with this huge, totally silent and empty deck was a truly unforgettable experience,” he said.

Coolest performance yachts

Some of the coolest yachts you can find come in the form of boats designed to break records or push the boundaries of the sailing world.

In terms of both these remits, it’s hard to look beyond the world’s fastest sailboat, Vestas Sailrocket 2. Sailrocket was built by Paul Larsen and his team with one aim, to break the sailing speed record.

It’s fair to say they were successful, even if it took many years of tweaking and development to get there.

But get there they did, and in November 2012 Larsen and his team achieved a 500m run with an average speed of 65.45 knots, smashing the previous record.

It’s no surprise, then, that designer Pascal Conq (of the famed Finot Conq design office) selected Sailrocket 2 as his pick from coolest yacht.

Another record setter is also a popular choice in this category. Yachting World writer and Vendèe Globe sailor, Pip Hare selected the ocean-going foiler Hydroptère as her pick of coolest yacht.

The Hydroptère team’s ultimate goal was the outright sailing speed record over 500m. In 2009, they pushed this to 52.8 knots, and in the same year set a record of 50.1 knots over a one-mile course.

Hydroptère was well ahead of the world in terms of technical innovation and was foiling across oceans years before the Ultime trimarans were getting up on foils. A true trend setter and design achievement.
Coolest historical yachts

There are many sailors who value tradition over and above outright speed, impressive size or technical innovation.

Another yachting photographer, Rick Tomlinson picked Jolie Brise as his selection for coolest yachts.

For those not in the know, Jolie Brise won the very first Fastnet Race in 1925 and is still constantly sailing. Owned by Dauntsey’s School, she is crewed by students who regularly sail her across oceans.

Even older than Jolie Brise, however (and currently sitting in the position of the oldest coolest yacht we have seen nominated), is Mayflower.
Round the world sailor, turned world-girdling cruiser, Pete Goss nominated her on the 400th anniversary of the famous Pilgrims’ voyage from Plymouth to the New World.

The Cherub is a 12ft two-person dinghy with a single trapeze (twin in the UK), designed in 1951. It evolved into an international development class, with a wide range of…

My choice would be the yacht Reliance of 1903 designed by the famous Nat Herreshoff. I read the book Temple to the Wind a long time ago and could not…

Aquitaine Innovations was 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 and the…

I was so fortunate to be working with an owner in Jim Clark who had a vision of all speed/no compromise. He was dared by a couple of Australian 100-footer…

“I stepped on board Volvo 70 Puma for the first time in Southampton to start trials for Team SCA for the Volvo Ocean Race. I’d just come from the Olympics…

Westward was designed by the great Nathanael Herreshoff and launched in 1910 and at 96ft LWL (135ft LOA) the steel schooner was the largest yacht Herreshoff had built so far.…

“What I love about My Song 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…

“What sets Pride of Baltimore II above all the other boats I’ve encountered is the combination of the boat itself, her captain and crew, her history and what she represents.…

“Kuka Light is the most extreme keelboat I have ever sailed,” explains Mitch Booth. “At 42ft and built in an autoclave she is VERY light and stiff. But when you…

“I would take a complete crazy thing: a Snipe. I think it’s an excellent boat for kids to start sailing in, and even for grown-ups. I have a Snipe dinghy…

“I’ve been fortunate to race on board and race against a great many boats I could nominate for my Coolest Yacht, but for me it would have to be the…

“This choice is made out respect for the boat (and crew),” says Rick Tomlinson. “There is nothing new in sailing, it’s all been done before by someone. Jolie Brise is…

I’d choose the MOD70 without too much doubt because the boat is so beautifully thought out. It is a great combination of speed, safety (even though four of them have…

“I’ve climbed a lot of mountains so choosing the coolest is a tough one, but it has to be the J Class Topaz. I love what we are able to…

“I’d been intrigued by solo or short-handed sailing since the early days of the BOC Challenge (Around Alone 5 Oceans) and was blown away by the wide beam Finot-Conq designs…

“I thought Hydroptère was the most incredible boat for a long time,” says Vendée Globe solo sailor Pip Hare of the groundbreaking 60ft (18m) foiler. “It was the first flying…

“In 1983, at 16 years old, I dreamed of building my own keelboat. An IOR Half Tonner was the top of my list, but I soon realised this was far…

“For me ‘Moby’, as Ellen MacArthur’s trimaran was known, is one of the coolest yachts,” says top yachting photographer, Thierry Martinez of Ellen’s B&Q Castorama. “In this photograph Ellen is…

“For my most influential boat, my mind drifted to the story of Swallows and Amazons, which gripped me as a child,” Nikki Henderson recalls. Arthur Ransome’s much-loved tale of children…