The ferry pulled out of Circular Quay in downtown Sydney in early January, bound for the nearby coastal enclave of Manly, one of my favorite beach towns in all of Australia. Fittingly, as the vessel made its way into Sydney Harbour, it passed close abeam to the iconic Sydney Opera House, with its celebrated curved white roof that has often been compared to the billowing sails of ships at sea. It had been almost 20 years since I was last on these waters, but I was suddenly awash in a gusher of memories. Through the years, Sydney and sailboats have played powerful roles in charting my own course through life.
My sister’s ex-husband was an Aussie America’s Cup sailor named Peter Shipway, which is how I found myself hoisting a spinnaker on the foredeck of a famous race boat called Love & War as it led a fleet of 150 boats into the harbor in 1988 to reenact the arrival of the first fleet of British convict ships for the country’s bicentennial celebration. It not only gave me a fresh appreciation for the history of a wild land that I’d come to love, but it was also my first sail in Sydney. It wouldn’t be my last.
A few years later, I was back, this time as the media manager for the BOC Challenge solo round-the-world race. My job entailed crashing out through the prominent Sydney Heads on a RIB with race director Mark Schrader to greet the incoming racers, lead them into port, and get the first interviews for my race reports. Schrader and I became great sailing mates, but that wasn’t the only important connection I made. It’s also how I met a lovely Aussie gal working for the event, Carole, who became my wife.
The next time I was in Sydney was to sail out through those heads myself, on an ex-BOC race boat called Spirit of Sydney, bound for the Tasmanian capital of Hobart, and then on to Antarctica on an expedition to Commonwealth Bay in support of a crazy Aussie pal named Don McIntyre, who’d spent a year there at the old camp of legendary Aussie explorer Douglas Mawson. After covering the BOC, I was desperate to witness the tempestuous seas of the Southern Ocean with my own eyes. Before all was said and done, we’d weathered 60-knot gales and the steepest waves I’d ever seen. I got a big taste. And then some.
Finally, I had one more Aussie line item on my personal bucket list—to sail one of the world’s greatest ocean races: the Sydney Hobart. In 2007, I finagled a ride on one of the smallest boats in the fleet, a 35-footer called Morna. We had a bit of everything: the classic spinnaker run down the coast of New South Wales, a thrash across Bass Strait, the final stretch down the jaw-dropping beauty of the Tasmanian shoreline. It was everything I’d hoped for. Even more.
Alas, Carole and I are no longer together, but the wonderful result of that union was alongside me on that Manly Ferry: my daughter, Maggie. After I voyaged around North and South America with my old mate Schrader, in 2011, Maggie was waiting for me on the docks in Seattle at the tender age of 11 when we finished the trip. I raised her as a single dad until she returned to Oz after the pandemic. Without Sydney, there’d be no Maggie. I can’t imagine.
We’ve done a bit of sailing together, including a memorable charter up the coast through the Whitsunday Islands. This was a trip of a different sort—a holiday excursion—and it was my last day. We hopped off the ferry and strolled down the beach, which gave me one final, welcome opportunity to drive her batty.
I’d forgotten to pack baggies, but there was no way I wasn’t taking one farewell Aussie dip, so I peeled off my jeans to my boxers and dived into the waves. With raised eyebrows, Maggie cast me a look of hopeless disdain, with just a trace of a smirk. I’d seen it a thousand times before; once again, it slayed me. With that, I had one more Sydney memory in my bank. The best one of all.
Herb McCormick is a CW editor-at-large.
