16 Mitala Street, Newport NSW 2106   Tel: 61 2 9998 3700


16 Mitala Street, Newport NSW 2106
Tel: 61 2 9998 3700


Checkmate Launches Aussie Assault at Pittwater to Paradise Regatta

Owner, Ray Roberts and crew of the iconic US-built Peterson 50, Checkmate are looking forward to launching the vessel’s Australian racing career in the 2018 Club Marine Pittwater to Paradise Regatta, which starts Tuesday 2 January.

Inclement conditions during delivery to Sydney from the Gold Coast resulted in damage that put the yacht, renamed Checkmate of Hollywood, out of this year’s Rolex Sydney Hobart Yacht Race.

As Michael Spies, seasoned sailor and long-time friend of owner Ray Roberts, explained: “We were pretty devastated not to make the Sydney Hobart, but with the adverse weather during delivery, we just weren’t prepared in time.”

Instead, they prepped and sailed Ray’s FARR 55, Hollywood Boulevard, which finished 10th, and are now flying back from Hobart in time for New Year’s Eve on Sydney Harbour, then a quick scoot to Pittwater for the Race start on Tuesday.

Checkmate is a sensational dual-purpose boat,” continued ‘Spiesy’. “She’s a proper yacht – nothing like the disposable boats we’ve been sailing for 30 or so years. We’ll watch the NYE fireworks on Sydney Harbour then get ready for the P2P.”

With her eye-catching gleaming timber hull, 50-foot Checkmate of Hollywood, with a sail number well-known to TV addicts of a certain age: 90210 (the Hollywood post code), is a 40-year-old IOR Doug Peterson design, built of Brazilian mahogany in San Diego by the illustrious Carl Eichenlaub, and updated in 2000 to make her a fast, competitive racing yacht.

In October 2017, Ray “Hollywood” Roberts bought the boat from the Orange County School of Sailing and Seamanship where she had given great service following her donation by the previous owner.

Roberts immediately sailed her to a win in her Class in the 53rd San Diego to Ensenada International Yacht Race.

Checkmatesailed from the US West Coast across the Pacific to Australia and cleared Customs at Southport Yacht Club at the end of November, before heading to The Boat Works on the Gold Coast for a thorough overhaul.

Roberts said Checkmate is one of the last cold-moulded wooden boats and unique in Australia. “It’s a showpiece and with her age allowance, we could be half a chance.”

The boat was originally commissioned for Monte E. Livingston who, apart from being one of Hollywood’s first entertainment Lawyers, was also one of Howard Hughes’ attorneys. He and his firm partner raised the funding for The African Queen staring Humphrey Bogart.

“You don’t see boats like this anymore,” said Joe Goddard, who oversaw the refit. ““Everyone who sees her is captivated. The stern is a lot fairer than the usual Peterson boats, making her a narrower, faster boat.

“It’s a middle-aged boat, but she is incredibly beautiful and fast. During the refit, we must have taken 500kg of junk off her, and with her new sail wardrobe and professional crew, with her IRC rating, she has really good odds.”

The crew comprises Skipper Ray Roberts, Michael Spies, Polish/international sailor, Filip Pietrzak who is Bowman, and Olympians and brothers, Jamie and Bobby Wilmot.

“We pride ourselves on a solid crew,” said Spiesy, adding “we have a good mix of old fellas who’ve been around the block”.

“We’re hoping to get a reasonable result in the P2P, given the time, effort, passion and money that have been invested in Checkmate of Hollywood.”

In terms of pedigree and potential, this exceedingly special, veteran yacht is one to watch.

“With our IRC rating we will be very competitive,” said Spiesy. “No older boat has been done properly in Australia. It’s our long-term plan to spend the next phase of her life creating a new tradition for this brilliant boat in Australia, then competing in Asia.

“In the P2P, we won’t be happy if we get screaming southerlies, but if it’s a mixed bag of conditions, it will be a tight race.”

Following the P2P, Checkmate of Hollywood will be berthed at Sydney’s Rozelle Marina and used as a training boat for the next generation of sailing talent. The Destination!The Destination!


The official weather briefing will take place at 9am on Tuesday 2 January at RPAYC.

For more information visit http://www.pittwatertoparadise.com.au/

Facebook: @pitt2paradise

Twitter: @Pitt2Paradise

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The Royal Prince Alfred Yacht Club - RPAYC is a yacht racing and sailing club based on Pittwater.

The yacht club offers year round inshore and offshore racing, cruising, centreboard dinghy racing, sail training and courses plus has a large marina accommodating up to 352 vessels.

There is also a modern boatyard with comprehensive marine services to help maintain your vessel.

Membership, including family membership is now available.

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