We ask top sailors and marine industry gurus to choose the coolest and most innovative yachts of our times. Well respected boat designer, Bill Tripp, picks the Herreshoff designed Westward as his selection

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.

Skippered by America’s Cup winner Charlie Barr, she showed unbeatable upwind pace thanks to her huge sail area.

“The sails are extremely good and balanced with what was the screaming edge of tech at the time,” explains Bill Tripp.

Westward was a schooner using the limits of materials at the time – the headsails put so much compression on the foremast, which is why they were schooners. The main mast didn’t have the headsail compression so the aft mast could reach for the sky.

“When they did the replica Eleonora they cut the bowsprit and mainsail down because they were scared by the thought of controlling all that sail as well as Charlie Barr could…”

Stats rating Westward

Top speed: 19 knots
LOA: 135ft/41.1m
Launched: 1910
Berths: 30
Price: $118,000
Adrenalin factor: 90%

Bill Tripp

Bill Tripp has yacht design in his blood – his father William H Tripp created many well known US designs. Bill Tripp’s designs include the 86m Aquijo, the largest sailing ketch in the world, the 62ft custom daysailer/racer Chessie Racing, Wally Yachts Esense and Saudade and design collaborations for Y-Yachts, Baltic Yachts and Solaris.

See the full list of World’s Coolest Yacht nominations.

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