Sailing holidays on Sydney Harbour: Blissful staycation

Sydney is not short of spectacular waterfront venues for a romantic night out, but there's nothing like seeing the sparkling harbour in all its glory from the water. Preferably on a large, elegant yacht set up for an overnight stay for just the two of you – and a skipper who does all the sailing business while you kick back with a glass of something delicious.

We board the gleaming, 12-metre James Chin at Sydney by Sail's private marina, handily situated in front of the Australian National Maritime Museum in Darling Harbour. "Is there anywhere special you'd like to see?" skipper Mike asks as we motor past the museum's collection of venerable vessels on one side and the ever-growing, ultra-modern Barangaroo site on the other. 

My husband is keen to start our three-hour afternoon cruise, the first part of an overnight stay aboard, with a trip to Cockatoo Island, so we head up the Parramatta River, marvelling at the mix of industrial buildings, imposing sandstone houses, ferry wharves and waterfront reserves in this part of the inner west. 

We set the sails just past the Harbour Bridge – and when I say "we", I mean Mike. Although we are competent sailors, it's a treat to do nothing more arduous than taking the helm on a boat trimmed for comfort rather than speed. Sydney by Sail offers a range of experiences – private charters, sailing lessons, tours and match races – and these Romance B&B packages are tailored for couples who can choose to do as much or as little as they like on the boat. 

We choose the latter option – and even though the wind is blowing a robust 20 knots, James Chin is perfectly designed for a smooth sail around the harbour. So smooth that as we whisk past Fort Denison, we open a bottle of wine and drink a toast to the beauty of the Emerald City. 

There's a lot to be said about the romance of sail – we are so in love with it, we were married on a vintage yacht – and it's no surprise Sydneysiders are taking to boating in unprecedented numbers since the pandemic struck. 

As we tack back and forth, making our way past Taronga Zoo, Mike points out landmarks and hidden coves. We circle back past Shark Beach (Nielsen Park), Hermit Bay, Shark Island and Clark Island, and before we know it we're back at the Opera House and sailing under the Harbour Bridge again. 

It's time to refurl the sails and motor towards Balls Head Bay, our anchorage for the night. Once Mike has dropped anchor and cut the engine, he checks everything is in place, bids us farewell and heads to shore in a dinghy. 

We go below to check out our luxury accommodation. Although the boat is three years old, it looks like new; there are blond-wood cabinets and a table in the saloon, comfortable seating with lots of cushions, a bright shower and bathroom and, best of all, plenty of headroom. Our bedroom in the bow is plenty big enough for two of us and everything is immaculately designed and, well, stylishly shipshape.

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We can play our own music, cook on the gas stove (ingredients for a hot breakfast are stocked in the fridge), and watch TV, although I don't imagine that gets a lot of use when you consider the surroundings. We lounge on deck as the sun goes down, then dine on a delicious seafood platter and gourmet salads from that generous fridge. You can even book a chef to cook dinner for you before he or she discreetly disappears on a dinghy, an option Mike says is popular for marriage proposals. 

As twilight settles in, we see one or two people walking along the beach but otherwise we have this glorious bay to ourselves. The boat swings gently on its anchor chain, and apart from bursts of birdsong and the occasional hooting of boats from afar, all you hear is the water lap-lapping quietly against the hull. It is pure, heavenly peace. 

By the time night falls, lights around the harbour foreshore are winking and flashing, speaking their secret language to seafarers. Every navigational light has a directional meaning but tonight it's enough to gaze at the spectacle and colourful reflections across the water. 

Navy divers from nearby HMAS Waterhen are up and about early the next morning and ferries are already criss-crossing the harbour. We enjoy doing nothing but cooking and eating a leisurely breakfast until our skipper arrives in the dinghy to steer James Chin back home. It feels as though we've been away for days – our love affair has fresh wind in its sails. 

The writer was a guest of Sydney by Sail; sydneybysail.com.

This article appears in Sunday Life magazine within the Sun-Herald and the Sunday Age on sale February 14.  To read more from Sunday Life, visit The Sydney Morning Herald and The Age.

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