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.

Sam Davies’ entry in the 2020 Vendée Globe was Initiatives-Coeur 3, a well-proven Verdier-VPLP design (ex Foncia/Banque Populaire/Maître CoQ III) that had been reoptimised with second generation foils fitted –…

The Open 7.50 is the fastest one-design sportsboat ever built. Designed by the Finot Group, it applies much of the developments from Open 50s and 60s ocean racing designs to…

Amaryllis, and her replica Amaryllis II, are among the coolest yachts. I had the opportunity to see her in the Herreshoff Museum in Bristol, Rhode Island, during the 2010 Little…

The highly competitive Class 40 fleet has long been a proving ground for talent, both for designers and sailors, with many going on to the IMOCA class. “I’ve had the…

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…

“For sure one of the coolest yachts is none other than the RC44 class created by Russell Coutts,” nominates Cameron Appleton. A strict one-design, the RC44 was co-designed by five-time…

“I always have been impressed by the dhow, the traditional racing boats sailed in the United Arab Emirates,” says Bruno Dubois. “The 60ft yachts are particularly impressive.” The original dhow…

“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…

The Maxi 72 Ran II was a dominant force both inshore and offshore, sailing an intense programme after its launch in 2009, including taking back-to-back wins in the Rolex Fastnet…

Terry Hutchinson is tactician for the Quantum Racing TP52 and nominates the team’s Botin-designed USA 52018. “The most recent Quantum Racing and this entire generation of TP52s have been a…

“The J/105 revolutionised downwind sailing in the sport as the first boat over 20ft with a retractable bowsprit and asymmetric spinnaker,” explains J-Boats founder Bob Johnstone. “The system was pioneered…

“Watching the gracefulness of kitefoil racing had me mesmerised the first time I saw it,” explains Will Harris. “It is an example of pure efficiency and use of all and…

“A very modern boat for her times: very large stern (almost like today’s naval architecture) and semi-round bilge hull made her very fast in reaching – and with a flush…

“I’d like to be able to say the AC40 [Women’s and Youth America’s Cup foiler] because hopefully – fingers crossed! – I will be in it and it’s definitely the…

While hyper-luxury superyachts are clearly cool to look at (and would be very cool to own) there’s no denying that speed is cool and this collection of record breaking boats…

“I think the Cookson 50 is one of the coolest yachts on earth for several reasons. First, it’s designed by one of the most renowned yacht design firms on earth:…

“In terms of complexity for speed, there isn’t anything else which has such a good ratio as a MOD 70. We’ve been over 40 knots [boatspeed] on them, and with…

America True was a ground-breaking campaign for the 2000 America’s Cup. Created by Dawn Riley, it was the first America’s Cup syndicate to be headed up by a woman, and…