There is a deliberate irony painted on the transom of Bill Kidman’s 1994 Murray Ross 12. Pretty Boy Floyd shares her name with the Depression-era American bank robber who won public favour by destroying mortgage documents during his heists.
Yet, this high-performance racing machine was originally commissioned by New Zealand rich-lister Eric Watkins and built by Kerry Alexander in Brown’s Bay. Now, after a lifetime of ocean racing across Australia, Noumea, Fiji, and Tonga, she is facing her purest test: the 2026 Solo Trans-Tasman Challenge from Opua to Southport, Queensland.
Murray Ross is known for designing high-performance racer-cruisers. She’s stylish; a red hull under clean white decks. You can’t but help admire her lightweight racing feel.
She’s about 3.8-metres across her beam; with that comes a sense of space. She needs it; her steering wheel, at my closest guess, is about 1-metre in diameter, perhaps even larger. It is indeed massive.
Downstairs she’s built as a racer, built to take the rough and tumble. For that lightweight endurance, which she’ll take to the open ocean with. She has raced her whole life, spent time in Australia, and been to Noumea, Fiji, and Tonga. Murray Ross himself sailed her shorthanded on occasion.
Kidman’s sailing history goes back to before he could reliably remember. His parents had a K class, Norseman, then a half-tonner, Thrasher, then a Young 88. By the time he was racing properly, he was on Ross 930s, eventually building his own 8.5-metre Murray Ross boat, Dodge Taxi. He did the Round the North Island two-handed in 1999. He has raced keelboats, multihulls, skiffs, and dinghies, and built enough boats to have formed strong opinions about all of them.
He has spent the past year preparing Pretty Boy Floyd for the Solo Trans-Tasman. New rod rigging handled by New Zealand Yacht Services. New batteries. Water ballast to compensate for the absent crew. A Starlink aerial. Fresh paint, a prop treatment courtesy of Propspeed and International Yacht Paint, and a full below-waterline system from Altex, the work done through Bay of Islands Boatyard. She looks, as Kidman points out without much modesty, like a racing boat. Because she is one. And she looks formidable.
On Saturday at noon, Kidman will leave Opua and point Pretty Boy Floyd at Australia, alone, in the 2026 Solo Trans-Tasman Challenge.
The decision to enter crystallised about a year ago, after a knee replacement. The Trans-Tasman had been on the list for years, sitting there the way big things do when life keeps getting in the way. Running the Great Escape Sailing School and Yacht Charters with his wife Julie for nine years, then selling it. Before that, two offshore family cruising trips in the 14-metre cat he designed and built himself, Synchronicity. The race kept getting deferred. Then came the knee, and with it the clarity. If not now, when?
“Do it today,” he says, “because tomorrow doesn’t exist.”
Sailing her solo will be a different proposition. The boat was designed for 12 people. The systems, the sail plan, the sheer physical scale of the thing, all of it assumes bodies on deck. Kidman has adapted what he can and accepted the rest. He operates primarily from the cockpit, within reach of the clutches and the sheets, sheltering under a large dodger he had made specifically for the crossing. A beanbag, a net rigged into the hatchway, multiple thermal cups of coffee. When conditions allow, he rests there rather than going below. Things happen too quickly offshore to be out of sight of the deck.
His sleep plan is a 20-minute cycle, around the clock. Day and night, a timer keeps him moving. Up, look around, check navigation, check for traffic, back down. From experience he knows it takes roughly two days to settle into properly. Exhaustion does strange things to experienced sailors, and Kidman knows it. He has prepared laminated checklists for every significant manoeuvre. Tack, gybe, sail change. Things you would never forget in normal circumstances become genuinely forgettable at sea on day three. He recounts a qualifying passage where, three and a half days in, he went through a tack and knew something was wrong. Couldn’t place it. Checked the list, looked up the main, and found he hadn’t let the runner go. The boat had been sailing, just not quite right. He fixed it and moved on.
That qualifying passage took him 170 miles offshore before a weather system that wasn’t in the forecast found him. He saw over 45 knots and six-metre swells. It wasn’t comfortable, but it was useful. A few things he thought he’d handle one way, he discovered he’d handle differently. Better to learn that 170 miles from home than 700 miles from anywhere.
The autopilot will do most of the driving. When conditions get difficult, particularly deep reaching in heavy air, Kidman expects to take the helm himself. It’s a fast boat in the right conditions. Light and reaching, he believes he can be competitive at the pointy end. On a hard reach, the bigger boats will likely pull away.
He’s realistic about the field. He names Sharon Ferris-Choat helming Vixen Racing, a Verdier 40, and Malcolm Dickson aboard Sarau, a Dickson 55, as the likely monohull front-runners. Wave, a Grand Soleil 50 helmed by Glen Jeffery, and Catnip, a Beneteau First 45 helmed by Geoff Thorn, are the benchmarks he expects to be racing against. He thinks Roaring 40, a Lutra BOC Open 40 skippered by Kevin Le Poidevin, with serious offshore miles under its keel, will be formidable. Kidman’s target is fourth or fifth. Anything better than that is a bonus.
Pretty Boy Floyd departs Opua at noon on Saturday. Destination: Southport, Queensland.
I think Bill might find himself pleasantly surprised by the end of the race.
