The Wonders of Oz

Sydney is the best port of entry. It’s usually the cheapest destination from North America, and the New South Wales capital puts you at the hub for all domestic flights. It would, however, be a mistake to hop straight onto a domestic flight when you arrive; Sydney is an awe-inspiring city regardless of season and the Blue Mountains, an opulent outdoor arena, are only a two-hour train ride from the city center. And even though you’re officially heading to Sydney during the winter, banish any images of arctic winds and six-foot snow drifts; winters can get chilly, but temps seldom drop below 40 degrees and the days are often sunny, clear, and warm. Sydney-siders may consider it “freezing” but anyone used to a real winter will be fine if they follow the logic of layering. So don’t let the natives fool you—while visiting in July (the “dead” of winter) this year, I spied several folks decked out in full winter parkas, scarves, and hats (or “beanies” in local parlance). But they also wore flip-flops (or “thongs”) on their feet—winter attire donned in the name of fashion, not function.

Paradoxical wardrobes aside, Sydney’s elaborate coastline does mean the city’s tailor-made for summertime, which makes winter accommodations easy to find. It’s possible to save as much as $20 to $30 off summer rates (ask when making reservations for off-season rates, and check hotel website for special winter discounts). As with most major urban centers, there are a wide variety of options, from backpacker hostels in the red-light district of Kings Cross to boutique hotels like the charming Medusa (www.medusa.com.au/sydney-hotel-medusa/) or the apartment-style Medina Grand Harbourside (www.medinaapartments.com.au) in the swank Darling Harbour neighborhood.

Outside of discounted accommodations, however, there’s not a huge amount of off-season savings in Sydney. But you will notice—and enjoy—the dearth of tourists. For example, the spectacular Bondi to Bronte Coast Walk—a two-mile paved route starting at the northeastern tip of Bondi Bay and weaving along the city’s serpentine coastline past Bronte Beach to the Waverley Cemetery, arguably the most envious final resting place in the world)—is chock-a-block with joggers, dog walkers, and strollers during the summer, but it can be your own private scenic jaunt from June through September. OR head to Sydney Harbour National Park and choose from a swath of hiking trails. Learn-to-surf “Surf-faris” are easy to organize, crowds at the New South Wales Art Gallery are nominal, and cafés lining Sydney’s beaches are populated by locals, not tourists sporting tropical shirts.

As the coast-to-coast walk will indicate, Sydney is a massive city poured around the intricate, amoeba-shaped Sydney Harbour hemmed in by national parks to the north and south. It’s impossible to get a full appreciation for the intricate waterways—the harbors, bays, and beaches—while on terra firma. A few options should therefore be considered. At the lower end of the economic spectrum, forego the Harbour Bridge Climb (which costs as much as AUS$225 for a twilight ascent) and head for the bridge’s South East Pylon where you can climb the 200 steps and take in stellar views of the Opera House and Sydney Harbour for under AUS$10. Or take a three-hour sail for AUS$130 into the harbor itself with Sydney by Sail (www.sydneybysail.com), a friendly outfitter based in Darling Harbour next to the Maritime Museum—and for the more ambitious, they do have discount mid-season charter rates available.

Or see Sydney the way you have to see it: by seaplane. A ride over Sydney Harbour toward Bondi Beach, then further up to the city’s national-park-lined northern beaches costs AUS$125 and is worth every cent; it’s really the best way to appreciate the region’s labyrinthine coastline. On our one-hour jaunt we enjoyed a staggering aerial view of the city’s landmark arched bridge and Opera House in full, sun-glinting splendor, and caught sight of a family of dolphins swimming in a long line in the azure waters off Bondi Beach. Sydney Harbour Seaplanes (www.seaplanes.com.au) departs from the pastoral Rose Bay and offers a wide variety of options, from half-hour jaunts to full-day, catered flight-and-hike trips. And don’t flinch at tossing $100+ at such indulgences—remember, you already saved big by flying during the off-season.