By day, Grace Shipway is a Senior Property Manager at Charter Hall. By weekend, she charters a much more temperamental environment – the ocean. Born into a family of sailors, Grace knew from a young age that she would one day be aboard a boat on one of the most difficult yacht races in the world, the Sydney to Hobart Yacht Race – and what better yacht to compete on than Love & War, the race’s three-time winner (once sailed by her father, Peter Shipway). This year she marked her second Sydney to Hobart Race, steering the yacht across the finishing line in Hobart in a competitive third place, and cementing her place as a seasoned veteran in one of Australia’s most demanding sports.
Can you tell us a little about your path after leaving St Andrew’s – where life has taken you since your time at the College?
Since leaving Drew’s, I’ve spent the past five years working in Commercial Real Estate. Outside of work, I’ve always been drawn to life on the water – from the intensity and camaraderie of surfboat rowing with Palm Beach, to more recently stepping back into the world of yachting on Sydney Harbour.
How did you come to competitive offshore sailing, and what drew you to the Rolex Sydney to Hobart specifically?
I came to competitive offshore sailing somewhat organically. What started with my Dad pushing me off a beach in Vaucluse in a dinghy when I was five gradually evolved into yacht racing and, eventually, offshore sailing. The Rolex Sydney Hobart Yacht Race has such an iconic status – not just within sailing, but in Australian sport more broadly. It’s one of those events I remember watching every Boxing Day from as early as I can remember, always thinking, “One day, that’ll be me.”
The combination of endurance, teamwork, & strategy makes it unlike any other sporting experience I’ve had, which is what ultimately drew me to it. And with my Dad having completed 31 Hobarts himself, I figured I’d give it a shot… not to mention the party on arrival – that’s pretty good too!
What was the experience of the race like – the conditions, the crew, the moments that stood out?
I remember dialling into the official weather briefing before the Boxing Day start, where the meteorologist outlined some fairly intense conditions for at least the first 48 hours: a 25+ knot southerly with waves forecast to exceed three metres. As a first-timer, I was definitely nervous. But the moment I stepped aboard Love and War, I immediately felt reassured by the experience and calmness of the crew around me.
I was sailing with 10 other crew whose combined Hobart experience totalled more than 150 races, so I knew I was in very safe hands. That level of experience, teamwork and composure under pressure was incredible to witness firsthand. The boys definitely looked after me!
Heading into those conditions was intense from the outset. As we turned right out of Sydney Heads and pointed south towards Hobart, I knew we were in for a serious few days. Waves were crashing over the bow as we pushed through a strengthening southerly, and life onboard quickly settled into survival mode. The crew was split into two watches, rotating three hours on and three hours off for most of the race – a routine that sounds manageable on paper, but feels very different when you’re cold, wet and constantly being thrown around offshore. Even going to the toilet was an absolute mission! (sorry for the TMI).
One of the moments that stands out most was finally sighting Hobart on day four. After 4 days at sea, minimal sleep, seasickness, surviving he cold, and such demanding weather conditions, seeing land again – and realising we were actually going to complete the race – was a pretty incredible feeling.
What did the race teach you – about sailing, about yourself, about working under pressure?
The race taught me a lot about composure. In offshore sailing, things rarely go exactly to plan, so you learn very quickly how important adaptability and clear communication are. It reinforced the importance of staying calm under pressure, trusting the people around you, and focusing on the next task rather than becoming overwhelmed by the things to come.
Are there any qualities or experiences from your time at St Andrew’s that you feel shaped who you are today?
Definitely – my time at St Andrew’s College played a big role in shaping who I am today. Being involved in Rosebowl Rowing at College was a standout experience for me. The teamwork required really carry through into a lot of what I do now. It taught me how to show up consistently, back the people around you, and perform as part of a crew rather than as an individual. And of course, Drew’s is never shy of a good celebration on the finish line – that sense of camaraderie is definitely something I still chase!
What’s next for you – on the water or beyond?
I’m still sailing most weekends, always learning and developing through different roles on the boat, and continuing to be mentored and coached by more experienced sailors. It’s a constant process of improvement, which is what keeps me coming back.
Looking ahead, I’ve got a pretty full sailing calendar. This year includes both summer and winter seasons, Hamilton Island Race Week, and then rejoining Love & War for the Cabbage Tree Island Race and the Classic Yacht Regatta, before once again making the journey south for the next Rolex Sydney Hobart Yacht Race.
Is there anything you’d like to say to current students who might be considering pushing themselves into new and unfamiliar territory?
Get mentored, put yourself out there, and don’t wait until you feel completely ready – back yourself and go for it. Some of my best experiences come from stepping into situations that initially feel out of reach, and this was certainly one of them. I definitely didn’t think I could achieve it at the time, but that’s often exactly the point. And if you’re thinking of heading south for a Hobart Race… definitely pack plenty of thermals!