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San Francisco Yankee Visits the Land Down Under for Rolex Sydney Hobart Yacht Race

Each year in the Land Down Under, while most of the world is still trying to figure out how to install batteries in their new Christmas gadgets, an intrepid group of sailors heads south to the land of wombats for the Rolex Sydney Hobart Yacht Race. The day after Christmas may seem a strange time to be starting a yachting competition, but the sun is up over 14 hours a day and folks from all over the world descend upon Sydney, Australia, to test their skills against some of the world’s fastest — and certainly largest — ocean-racing thoroughbreds.

The course stretches more than 600 miles across the Bass Strait, and has caused many sailors to rethink their decision to even start. In a good year, the 100-ft maxis are finished racing less than two days later, sometimes a lot less. This race has always had the reputation as a gear buster, and this year’s 80th edition lived up to the hype.

The Rolex Sydney Hobart fleet heads out of Sydney Harbour on Dec. 26 (AEST).
© 2026 Chad Stenwick

Generally, it takes a world war or COVID pandemic to prevent sailors from completing this course. This year, nearly one-third of the 128-boat fleet ended up heading for safe harbor due to high winds and brutal seas. The race committee takes its job seriously. The safety requirements would sink a Cal 20. Each vessel must complete inspections by three different inspectors while hauled at a yard. The hull keel joint is examined, the rudder and bearings are surveyed, and many more critical measurements are confirmed to ensure stability. Each competitor is required to have a PLB and EPIRB in addition to a life jacket and harness no more than a year old, with sales receipt to prove it.

The Richmond Yacht Club contingent, led by Commodore Jim Quanci (also chief of 2027 Pac Cup and commodore of the Singlehanded Sailing Society), Dave Garman and Andy Schwenk, were ably assisted by fellow Yanks Valerie Bucholtz, Greg O’Toole and Chad Stenwick. This crew of six joined captain and owner John Wilkerson aboard the venerable Express 37 Perplexity for this epic jaunt.

The epic jaunt included spectacular sunrises.
© 2026 Chad Stenwick

Interestingly, this vessel was the only yacht flying the Stars ‘n’ Stripes to make it from the land of making sailing great again to the land of convicts, kangaroos, and koalas on her own keel. Did I mention Wilkerson sailed her to Australia singlehanded? Even though this salty bunch of sailors had completed, among us, more than 75 transpacific crossings and dozens of other bluewater passages, this was not enough to meet the strict safety protocols. Perplexity slipped her Sydney mooring lines on December 20 to complete the required 150-mile foray into the South Pacific whale pasture to check off another box on the required safety list.

Perplexity crew hams it up before sailing out of Sydney.
© 2026 Valerie Bucholtz

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*Note: The February issue cover photo, taken by Valerie Bucholtz, is of Perplexity crew Dave Garman at the helm during the Rolex Sydney Hobart Yacht Race.

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