The airplane ride to Australia is impossibly long. Owing to time zones and the space time continuum and physics that I do not care to understand, an entire day actually just disappears while you are flying over the ocean. I left the U.S. on a Tuesday afternoon and touched down in Sydney on Thursday morning. Good riddance, Wednesday. It was trippy.
So, after all that consecutive siting, a walking tour seemed like the best way to get started. Sydney is just like every city you have ever visited and totally different from anything you have ever seen, all at once. You think you are looking at a run-of-the-mill palm tree, and then you realize there is a flock of wild cockatoos living in it. And that regular looking meadow? It is no doubt home to wallabees.
Exploring on foot is the best way to ensure you don't miss a thing, so here is a great loop that takes you past all the very best Sydney has to offer. The whole route is about 2.5 miles (4 kilometers, if you're into that) and should take you about two-and-a-half hours. Plenty of food and drink can be found along the way.
Hop the train to Circular Quay (pronounced "key") and start your morning on Observatory Hill, near Watson Road.
The copper-domed Sydney Observatory, and the Hill itself, offer a stunning vantage of Millers Point and the harbor. You might be interested to know that Observatory Hill was the site of the fledgling Australian colony's first windmill, erected in 1796. These days, Observatory Hill is a favorite destination for dedicated joggers and lunchtime crowds escaping Sydney's nearby Central Business District (CBD).
Once you have soaked in all the loveliness, take a winding walk down to Argyle Place, a charming English-style village green lined with equally charming terraced houses. Also worth noting: any Australian has the legal right to graze livestock here. (Pass it on!)
Across the road and slightly to the west, you'll find Lord Nelson Brewery Hotel.
The "Nello" started life in 1836 as a private residence, and was converted to a pub in 1841. It might be the oldest continually licensed hotel in Australia. But others make the same claim so, then again, it might not be. Test out an brewed-on-site stout or ale, if you'd like, and then head back down Argyle Place and hang a left at Lower Fort Street.
At the corner of Windmill Street you'll come to the Hero of Waterloo, another contender for oldest pub in Australia (we'll let you be the judge). Come back at night for some piano, folk, jazz or Celtic music. And, if you're brave enough, head downstairs to the original dungeon where drinkers would sleep it off before shipping out to the high seas.
If you take another left, you'll find yourself on Ferry Lane and at the foundations of Arthur Payne's house. He has the distinction (?) of being the first victim of the 1900 bubonic plague outbreak. Poor guy.
Next, double back along Lower Fort Street to Garrison Church, also known as Holy Trinity, the colony's first military church.
Australia's first prime minister, Edmund Barton, also attended school here. If you head left back down Argyle Street, you'll walk through the Argyle Cut, a convict-excavated tunnel that was finished off with a few sticks of dynamite in 1867. Ah, technology!
Just past the Cut you'll see a set of stairs on your left. Head up and along Gloucester Walk to Foundation Park, settled in the preserved ruins of an old tenement building and now filled with oversized furniture by artist Peter Cole, evoking the cramped conditions once experienced by working class families in the area.
Continue along Gloucester Walk, turn right into Atherden Street, and then right again past the terraced houses of Playfair Street. Cross Argyle Street into Harrington Street (still with me?) and then jog left into Suez Canal, a notorious lurking point for 19th-century goons. I think it's pretty safe now, but no need to linger.
Instead, turn left onto St. George's street (Syndey's oldest road), and head down the stairs to the right to Cadman's Cottage. Originally constructed in 1816 for Governor Coxswain John Cadman, Cadman's Cottage is Sydney's oldest house. The Sydney Water Police detained criminals here in the 1840s, and it was later converted into a home for retired sea captains. These days it houses the Sydney Harbor National Park Information Center, but there is also a small museum with a few exhibits.
From there, follow Circular Quay east and to the Museum of Contemporary Art. Admission is free, so it's a good place for a quick art fix, or a quick coffee at the cafe. The constantly rotating exhibitions at the MCA are well-known for raising eyebrows and controversy.
Once you've had your fill there, cut underneath the Circular Quay train station and you'll find yourself at the newly renovated Customs House. The harborside edifice houses the three-level Customs House Library, with a great selection of international newspapers and magazines to browse. Keep your eyes peeled for the swastikas in the tiling in the lobby, as well as a plaque describing their symbolism. If you are famished at this point (and I imagine you might be), head to the Cafe Sydney on the top floor for can't-be-beat views of Sydney Harbor and delicious seafood and wood-fired dishes.
Back down at the Circular Quay ferry docks, take a quick walk along the Sydney Writer's Walk, marked with circular metal discs bearing the innermost thoughts and ruminations of Australia's most prominent writers, Robert Hughes, Germaine Greer, Peter Carey, Umberto Eco and Clive James among them.
And then you will find yourself at Sydney's piece de resistance, its shining glory, its crown jewel. The Sydney Opera House.
I am not exagerrating when I tell you that I came home with nearly 100 pictures of just this building. You simply cannot take your eyes off of it. (Though try to tear your gaze away long enough to take in a great view of the Sydney Harbor Bridge off to your left.) I highly, highly recommend investing the time and the money (about $35) in a guided tour. The history of the Opera House, from its salvaged design to its over-time and over-budgeted construction, is endlessly fascinating. Plus, a tour means an inside look at some of the Opera House's six auditoriums. And, if you flash your tour ticket at the box office, you can score majorly discounted tickets to current performances. I saw the Puccini opera, Tosca, for $20. It was heaven.
Finish up your stroll by following Bennelong Point along the water's edge to the gates of the Royal Botanic Gardens.
The garden is free, and visitors are invited to sit on the grass, smell the roses and hug the trees. It is a very inviting place, indeed. The exotic plants and flowers will captivate you for as long as you care to stroll, and be sure not to miss the rare Wollemi Pine, an ancient tree only discovered in 1994 in the nearby Blue Mountains. Other highlights include the rose garden, the South Pacific plant collection and the prickly arid garden. Guided tours are free, last for one-and-a-half hours and leave from the Gardens Shop. And you can eat the best meal you might ever have on the whole continent at the Gardens' restaurant. If you are in or near the Gardens at dusk, you'll be keeping company with the large and rather vocal colony of bats that feeds there every night. They totally creeped me out at first, but appear to be harmless.
And then, I would say, you will have done Sydney right.
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