The Hot and Fleeting Relationship of Sydney

Ahhhhh, Sydney.

Sydney is that really good-looking guy, who is really inconvenient, that you never get over. Sydney is breathtaking, whether you’re walking the pristine coastline, watching the sun go down from Mrs. Macquarie’s Chair, or enjoying one of the many views from the harbor itself on a ship. It merits a trip halfway around the world just to get there.

However, to make it as convenient as possible to explore the city, I’ll stick to four basic areas: Circular Quay, Manly, Bondi, and Surry Hills. Be forewarned: Sydney isn’t cheap. The prices will make NYC seem like a bargain, but it’s worth it.

The Quay:

All buses and ferries seem to lead to Circular Quay, and most visitors navigate their trips from here. It’s a fantastic place to people watch: you’ll get to witness everything from Aborigines playing didgeridoos, brazen magicians with super-bougainy accents, and tourists from all around the world. When ships aren’t in port, I recommend grabbing a spot near the Overseas Passenger Terminal (Cruise Bar, a funky cocktail lounge with patio seating, and Wildfire, a fine-dining grill with outdoor heaters, are both good options).

This spot would position you across from the Sydney Opera House, one of the world’s best views. If there is a ship in port, head to the other side of the Quay, which is just under the Opera House at Opera Bar. And don’t worry: you’ll have a view of the Sydney Harbour Bridge from this vantage point, and a panoramic view of the Quay. This is a good time to take stock of what you’re drinking down under. Australia has a number of wine regions, and you’ll find them all on the menu here. While Australia is known for its Shiraz, I’d also recommend wines from the Margaret River Valley.

Manly: [sociallocker]

“Seven miles from Sydney and a thousand miles from care.” Hop a ferry from the quay (be sure to get in line EARLY for the ferry to jockey with other aggressive tourists for the spots that will face the Opera House as you pull out—it’s worth every Kodak moment). Over the course of the thirty-minute ride, you’ll pass more sailboats that you’ve ever seen total, the naval base at Woolloomooloo, and get to peep through the mouth of Sydney Harbor out to the Indian Ocean and beyond.

Once you arrive at Manly Wharf, you’re looking for a view, and of course, you’ll have several options. If you’re not a beach lover, you’ll still love Manly. It has an old-timey feel, from the architecture to the long time north-side residents you meet during your visit. The Manly Wharf Hotel is a great place to grab an outdoor drink or snack near the wharf. Wander down to the beach, which will lead you to the hilarious tourist shops along the way and some seriously cool Australian beach gear. End your ramble at the Hotel Steyne (many of Sydney’s best watering holes have “hotel” in their names), and wind your way upstairs to Moonshine, a cider and rum bar (16 ciders on tap, and even more in bottles). Here, sample all varieties of Australian cider before you settle on one, and head out to the slender bar that overlooks Manly Beach and the boardwalk. The beach is a busy hive of activity: surfing lessons, beach volleyball games, and ill-prepared tourists colored a painful shade of pomegranate. Due to the sun’s extreme power here, I recommend SPF 70 for even a peep out in the sun, although every Australian you meet will argue that anything over 30 is nonsense.

A trip to Sydney wouldn’t be complete without a trip to Bondi. Take the iconic Bondi-Bronte walk and prepare your senses for even more views. On your way back, if you’ve brought along your international passport, you can stop in Icebergs, with its famous pool filled by the ocean. My favorite place to kick back is The Bucket List, which is right outside the Bondi pavilion. Sink into a beanbag with a pitcher of cocktails and watch the world run, walk and surf by you. Note: The bartenders are an integral part of the view, as well.

Surry Hills:

Simply put, Surry Hills out-cafes Vienna, Paris, and any other place claiming coffee supremacy. You can’t walk into a café in this part of town without getting a fabulous cup. Most shops have relationships with their growers, and all are delivered with a cheeky accent. They’re even better with a bacon-and-egg roll. There are several sauce choices, but I recommend the tomato relish. Beware, though, the bacon is not of the American sort (which, really, should make you even more keen to try it).

Some standouts are: Kawa (a shabby chic café frequented by locals and famous folk), Bourke Street Bakery (here, you can wash down a flaky sausage roll with a perfectly portable, freshly-brewed iced coffee bottle), and Twig (the interior patio is a tiny natural oasis in the city). Repeat each day as necessary in order to wash away the effects of the prior evening, in which you’ve spent too much time at some of the following water holes:

Shady Pines—This place is the carved-Indian, whiskey-serving, mock honky-tonk, underground bar that you’ve secretly been dreaming of having in your basement forever.

The Beresford Hotel—The back patio is one of the most glorious ways to spend a summer evening, and the interior bar features one of the prettiest showcases of old subway tile.

The Local—This tiny sliver of a bar has one of the best craft beer selections in the city. Try a paddle of 5 beers for $15. Suit your mood with either a comfy couch downstairs or a balcony seat upstairs. Enjoy interacting with the crowd—they’re endlessly entertaining.

Flinders Hotel—This spot is where you end your night, and ponder why you haven’t visited Sydney sooner. [/sociallocker]