The best way to absorb Sydney’s criminally fascinating history and culture without missing out on its great weather?
Hop a ferry to one of its harbor islands.
Cockatoo Island, Goat Island and Fort Denison are all within sight of the Sydney Harbour Bridge and a short ferry ride from the main terminal at Circular Quay.
Cockatoo Island
Don’t expect to see any of the sulfur crested squawkers the island was named after –- they've long ago flown off to the ‘burbs.
Cockatoo Island has been off limits to the public since Sydney was founded and opened to visitors only in 2005.
Cockatoo Island's industrial heritage shouts across the harbor with tall towers, rusty cranes and utilitarian buildings. You probably won’t be colored amazed to discover that the island started out as a convict prison. Governor George Gipps decided to stick them on Cockatoo in 1839 and get them building their own prison; as most convicts couldn’t swim it was the ideal solution.
Between 1850 and 1870 the Fitzroy dock was built by convicts to service shipping and in 1900 Cockatoo Island became the New South Wales Government Shipyard; the prisoners were moved elsewhere some years before.
The dockyard closed in 1992.
In other countries with such prime real estate and fabulous views of the city -- including the famed harbor and its bridge -- the government might have bulldozed the buildings and covered it in multi-million dollar apartments.
But Australia is a young country that cherishes its historic sites. UNESCO agrees. It added the island to its World Heritage list in 2010.
While there aren’t any holiday condos, you can stay in some of the heritage houses on the island or go "glamping" in one of the many pre-erected tents –- all you have to bring is a torch, sleeping bag and pillow.
Light sleepers be warned. Between the ferries, helicopters, planes and boat traffic it isn’t the quietest spot for a good night’s rest.
The facilities and view are beautiful though. A covered kitchen area with barbecues and microwaves is available. There’s also a shower block -- something the convicts would have given a limb for.
Missed the boat? Drinks at Cockatoo's Island Bar are a fine way to pass the time. All over the island are remnants of the shipbuilding it was famous for. During World War II, Cockatoo Island was the nation’s leading shipyard, with some 250 ships, including luxury liners and cargo ships, converted or repaired here.
Entry to the island is free and there are both guided and self-guided tours and free kids discovery books on both the shipbuilding and convict history.
Ferries depart frequently from Circular Quay, but check times for return ferries, which run less regularly. If you do miss one and have to wait, there’s a small café near the ferry dock.
A short walk away is the Island Bar. Constructed from recycled shipping containers, serving cocktails and wood fired pizzas, it’s a mellow place to watch the sun go down on the harbor.
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Goat Island
Goat Island, with Sydney in the distance.
What started as a stone quarry became the perfect place to store explosives.
While you can go freestyle on Cockatoo Island, you have to book to visit Goat Island through Cadmans Cottage on George Street at The Rocks, or through a Sydney boat tour operator –- these will often include more than one island visit if you want to make a whole day of it.
Goat Island and Fort Denison are part of Sydney Harbour National Park.
The government has put together some excellent guided tours, which point out the local wildlife, as well as bringing alive the history of the island. This naturally includes convicts kept in vile conditions, but also provides insight into the lives of the soldiers who watched over them.
It was fitting that all 771 episodes of the popular Sydney TV series "Water Rats" was filmed on Goat Island from 1996-2001, given one of the first water police stations in Sydney can be found here.
A tour of Goat Island is both fascinating and good exercise. If you haven’t any fat to walk off, we suggest opting for a "convicts, lunch and bubbles tour" to balance out any calories you might burn on the steep inclines.
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Fort Denison
The sandstone Martello Tower of Fort Denison in Sydney Harbour, one of Sydney's other landmarks.
Fort Denison is a spectacular place for lunch.
Across from the Opera House, right in front of the bridge, this tiny island has an excellent restaurant.
Not outrageously expensive, the food is good and the view sublime.
If it’s busy with groups, the marquee interior can make it feel a bit like you're crashing someone’s wedding, but it's well worth the trip. Reservations are essential, book online here. The restaurant is open only from 11:30 a.m.-3:30 p.m.
It’s ironic that you can chow down so comfortably on the island -- known as Pinchgut in the early days -- as, you guessed it, convicts being punished here were fed slender rations of bread and water.
Completed in 1857, the iconic sandstone Martello Tower is the only one of its kind in Australia. Today Fort Denison operates as a harbor navigation facility -- with automated tide gauge, foghorn, beacon and channel markers -- and as a museum, along with the restaurant.
Fort Denison is a five-minute boat ride across the harbor from wharfs at Circular Quay, Luna Park, Kirribilli, Woolloomooloo, Cremorne Point and Elizabeth Bay. For more info, visit the official Fort Denison website.
Still in the mood for island hopping? Other Sydney Harbour islands include the perfect picnic islands of Shark, Clark and Rodd. There’s also Bare Island, built to spare Sydney from a "back door attack" and the naval heritage site, Garden Island.
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