Every list of Sydney anchorages is just a list. The only question that matters at 10am is which way it will be blowing at 1pm.
Sydney has perhaps a dozen anchorages that are genuinely pleasant for a long lunch, and on any given day about half of them are wrong. The bay that was flat and perfect at ten in the morning becomes a lee shore with a metre of chop by two in the afternoon, and the only thing that changed was the wind.
From roughly October to March the default is the nor'easter. It is a sea breeze, so it is not there at breakfast; it fills in through the late morning, and by mid-afternoon it is commonly 15 to 25 knots, blowing straight up the harbour. Then, several times a summer, a southerly change arrives in the late afternoon and reverses everything in about ten minutes. Winter is different again: cold westerlies behind a front, usually strongest early, with long stretches of very light air in between.
So the useful way to think about anchorages is not a ranked list of favourites. It is a lookup table. Check the forecast for the afternoon, not the morning, and pick the bay that has land on the windward side.
You want a bay that opens to the south or the west, so the land sits between you and the breeze and there is no fetch for chop to build across.
Spring Cove, under North Head, is the standout. Store Beach and Quarantine Beach face west into North Harbour with the bulk of North Head to windward, so a strong nor'easter turns up as a breeze rather than a sea. Chinamans Beach in Hunters Bay is the Middle Harbour equivalent, tucked behind the Mosman ridge with sand to anchor in. And if it is really up, Bantry Bay and Sugarloaf Bay above the Spit Bridge are effectively immune.
Camp Cove, on the western side of South Head, works well in a plain easterly but gets restless in a fresh nor'easter, because the breeze has the whole length of the harbour to run down before it reaches you.
Now you want the opposite: a bay that opens north, with high land behind it to the south.
Athol Bay, under Taronga Zoo between Bradleys Head and the zoo wharf, faces north-west with the Mosman headland behind it and is the classic southerly lunch stop, though it collects ferry wash all day. Chowder Bay at Clifton Gardens is better protected still, sitting behind Georges Head with a beach and a wharf ashore. Spring Cove works here too, which is what makes it the most reliable anchorage in the harbour.
The southerly change deserves respect rather than panic. It arrives fast, often with a 20 to 30 knot burst and a sharp temperature drop, and it converts every north-facing anchorage into a lee shore in minutes. If a change is forecast for late afternoon and you are anchored somewhere open to the south, do not be the boat still setting a second anchor when it hits. Pull up early and go somewhere else, or go home.
There is no perfect westerly anchorage in the eastern harbour, and pretending otherwise is how people end up bouncing through lunch. A westerly has the entire east-west length of the harbour to blow across, so Rose Bay, Camp Cove, Watsons Bay and Athol Bay all get short, steep, cold chop.
The reliable answer is upstream. Sugarloaf Bay and Bantry Bay are cut into ridges high enough and steep enough that a 20-knot westerly arrives in fragments, and the upper Lane Cove River does the same job from the western side. If you are berthed at The Spit this is a fifteen-minute run. If you are at Rushcutters Bay it is closer to forty-five, which is worth knowing before you commit to a cold day.
The other winter reality is that most westerlies blow themselves out by early afternoon. Sometimes the right call is simply to leave later.
Shark Island off Point Piper, Clark Island off Darling Point and Rodd Island in Iron Cove are all Sydney Harbour National Park. Landing on them is not free and not spontaneous: you book and pay a landing fee through National Parks, which caps numbers and keeps them from being overrun. Shark Island has a wharf, lawns and picnic shelters and is the best of the three for a group.
The rules that go with them are simple and enforced. They close at sunset, there are no bins so everything you carry ashore comes back with you, and dogs are not allowed. Anchoring off Shark Island rather than landing is legal but exposed, and the tide runs past it hard enough to make a tender trip interesting.
Most anchoring problems in Sydney are social rather than technical. Arrive, look at how the boats already there are lying, and work out where you will sit when the wind swings, not just where you are when you drop. Do not anchor inside a moored boat's swinging circle. Give the swimming areas and netted enclosures a wide berth, and remember the four-knot limit inside 30 metres of anything.
Where there is a choice, drop on sand rather than seagrass. The beds in Middle Harbour and North Harbour are slow-growing and anchor chain scours them.
The honest note: on the first hot Saturday of summer, every good bay in Sydney is full by half past eleven and you will end up at your third choice. That is not a failure of planning. It is the harbour. It is also the single best argument for using the boat on a Thursday, or in May, when the list above is entirely academic because you can have any of them.
And if you have never set an anchor in 8 metres with a crosswind and an audience, book a skipper for the first few outings and watch how it is done. Nobody learns ground tackle from a manual.
Bantry Bay in upper Middle Harbour, for wind. It is surrounded by steep national park ridges with no road access and stays calm in almost any direction. For a beach stop, Spring Cove under North Head is protected from both the north-east and the south.
Usually late morning through early afternoon between October and March, building to 15 to 25 knots by mid-afternoon. Mornings are typically the calm part of a summer day, which is why experienced owners leave the berth early and pick their bay from the afternoon forecast.
Yes. Shark Island, Clark Island and Rodd Island are national park and require a booking and landing fee through National Parks. They close at sunset, dogs are not allowed, and there are no bins, so you take everything back with you.