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  • 44 Adams Ave, Malabar, Sydney NSW 2036, Australia
    Australia is world-renowned for scuba diving, but you don’t have to go all the way to the Great Barrier Reef or Ningaloo. Most people don’t know there is plenty of good diving in and around Sydney, too. One of the best sites is Magic Point off the tip of Malabar Headland National Park south of Maroubra. There’s an extensive reef system and large caves that are home to weedy sea dragons, stingrays, and a recovering colony of grey nurse sharks (which by most accounts are harmless to humans). Local outfitters such as Frog Dive Scuba Centres can lead you there.
  • Harbour St, Sydney NSW 2000, Australia
    The largest and most storied of the Sydney Harbour islands, Cockatoo was once an Aboriginal fishing ground, a naval shipyard, a girls’ reform school, and a gruesome prison. Today, it offers fascinating walking tours, a casual café, and a number of events such as the Biennale of Sydney. When most visitors line up in the evening to catch the ferry home, those staying on the island are just setting off on a leisurely sunset stroll. They can watch the city light up from what feels like another world and then retreat to their campsite, canvas “glamping” tent, heritage home, or modern apartment until they wake up to birds and boats the next morning.
  • 3 Vickers Street
    A bright space in Darwin’s Parap neighborhood, Nomad Art Gallery emphasizes limited-edition prints and collections produced by contemporary Australian Artists as well as Aboriginal art centers around Northern Australia. The focal point is cross-cultural collaborations between artists and master painters and etchers. In addition to the prints shown in exhibitions and sold online and through the shop, visitors can purchase textiles, books, and small sculptures.
  • Cowper Wharf Road &, Dowling St, Woolloomooloo NSW 2011, Australia
    The meat pie is synonymous with Australia, and no place is more iconic in Sydney than Woolloomooloo’s Harry’s Cafe de Wheels. What started out as a simple stand turned into one of the first food trucks when local ordinances dictated that mobile food carts had to move at least 12 inches every day. There are now dozens of Harry’s around Sydney, each serving up their famous pies. “The Tiger” is the most well known: a pie topped with mashed potatoes, gravy, and mushy peas. There are no tables to speak of, but rather a counter attached to the truck. Thousands of celebrities, politicians, and locals have flocked to Harry’s for their pie fix. And the place is open until 2 a.m., making it a great late-night spot.
  • George St, The Rocks NSW 2000, Australia
    The Rocks is undoubtedly one of Sydney‘s most beautiful areas. Follow George Street until the very end and it’s almost like you’ve stepped back in time—there are cobblestones under your feet, quaint stores to browse, and great pubs to visit. One of the best experiences you can have in Sydney is to visit the Rocks Markets, especially on Friday nights during spring and summer for the Rocks Markets by Moonlight. The warmer months in Sydney are the most exciting; pair them with all the beauty of the famous Harbour Bridge, Opera House and this historic hub and you’ve got the best version of this amazing city. There are stalls offering everything from handmade gifts and sweets to unique jewelry and fashion, but the atmosphere is set off by all of the other quirks that you would never have expected—puppeteers and magicians roaming the crowd, dozens of people young and old wearing headphones and dancing at a silent disco, musical performances and pet displays with some of the most enormous cats and rabbits you’ve ever imagined. All of this set among historic buildings and Sydney’s oldest sites makes for a truly unique experience indeed.
  • 66 Hunter St, Sydney NSW 2000, Australia
    The most stunning dining room in celebrity chef Neil Perry’s restaurant empire has got to be Rockpool Bar & Grill in Sydney. Seated amid soaring green marble columns and Art Deco windows in a space designed by Emil Sodersten, diners can choose between the finest steaks, seafood, cocktails, and wines—more than 3,000 of them—that Australia has to offer. Dry-aged beef and sustainable fish are simple yet succulent, cooked over an open flame or in the wood-fired rotisserie. Start with the signature Four Raw Tastes of the Sea before savoring the Wagyu or Cape Grim steak, or opt for classy appetizers and cocktails in the candlelit bar, adorned with 2,682 hanging Riedel riesling glasses.
  • 34 Harrington St, Sydney NSW 2000, Australia
    Chiseled from a sandstone-and-brick wool factory on the site of Sydney’s first hospital, the Harbour Rocks Hotel is one of the most historic accommodations in the Rocks—and maybe the most haunted. Hotel staff say part of the building, named Scarlett’s Cottages after a well-known lady of the night, is watched over by Eric, a man who once lived here and who still searches for Scarlett in the labyrinthine corridors after she swore her love to him and then disappeared. Ghosts aside, the hotel’s 59 rooms are peaceful, with high ceilings, Georgian arched windows, brick walls painted dark gray, Old West–style textiles, and wool carpeting that recalls the building’s former life. The place is filled with fun artifacts, too, from the ancient luggage lift to old maps and letters framed on the walls. The early-20th-century history that pervades the building is also found in every direction outside its doors.
  • Sydney Harbour Bridge, Sydney NSW 2000, Australia
    I love finding Love Locks all over the world. Sydney did not disappoint with a collection on the Sydney Harbour Bridge, with a perfect view of the Opera House.
  • 267 Darlinghurst Rd, Darlinghurst Sydney, Australia
    Owned by Terry Kaljo—a former model and founder of the Contemporary Hotels collection of upscale rental homes and villas—the Medusa Boutique Hotel offers 18 unique accommodations in Darlinghurst, an eclectic area and the epicenter of Sydney’s gay community. The 19th-century home is filled with wacky touches, from red Alice in Wonderland–style carpeting that runs up the grand staircase to pastel-pink walls studded with maple leaves in the entryway. The midcentury-modern rooms—with their retro primary colors, geometric patterns, and vintage chaises longues—attract fashion, media, and design professionals looking to get beneath the surface of one of Sydney’s liveliest neighborhoods. But there’s still the opportunity to relax, as guests can settle in next to the fireplace in the lobby to read the newspaper, enjoy a complimentary pastry, or make new friends. Longtime staff members offer the kind of local knowledge and personal attention that keeps guests coming back.
  • Bradleys Head Rd, Mosman NSW 2088, Australia
    Travelers should visit Taronga Zoo as much for its harbor views as for the 4,000 resident animals (who get to see them all day long). Ferry 15 minutes from Circular Quay and take an optional Sky Safari cable car, included in the ticket price, and you’re in an exotic land of giraffes, elephants, and bongos as well as native echidnas, wombats, and Tasmanian devils. Wildlife tours, zookeeper talks (including impressive bird shows), and special events such as the Twilight at Taronga summer concert series are on the calendar, and a tented camp accommodates overnight guests who help feed select animals before a sunset dinner set against the Sydney Opera House and Harbour Bridge. Tent cabins feature decks that lure campers out of bed for sunrise.
  • Sydney Harbour Tunnel
    There are certain touristy things that one must do while traveling. And some places are so great that even locals flock to them despite the fact that they’re heavily trodden. The Opera Bar at the Sydney Opera House is one of those places. There really isn’t a good reason not to hit happy hour at the Opera Bar. The drinks are reasonably priced, and the selection is impeccable. There is live music every night of the week and the vistas offered by the bar are some of the best in all of Sydney. Transportation options to and from the Opera House are plentiful not to mention that site-seeing and drinking almost always go good together.
  • 1 Notts Ave, Bondi Beach NSW 2026, Australia
    This 7.5-mile round-trip walk has some of the most amazing coastal views in Sydney and is a great introduction to the city’s Eastern Suburbs. Starting from Icebergs pool in Bondi, the path hugs cornmeal-sand coves, natural seawater pools, a marine reserve (Gordons Bay) that’s great for snorkeling, and unique attractions from ancient Aboriginal rock art sites to the oceanview Waverley Cemetery. In late October, site-specific art installations pop up along the cliffs between Bondi and Tamarama beaches as part of the Sculpture by the Sea exhibition, one of the largest outdoor sculpture events in the world. Spring (September through November) is also an excellent time to see migrating southern right whales spouting in the sunset. Toast your trek with a drink at the Coogee Pavilion.
  • 169 Dolphin St, Coogee NSW 2034, Australia
    A quick bus ride from the city (or a refreshing end to the Bondi to Coogee Coastal Walk), Coogee Pavilion is one of the most happening beach bars in Sydney. The downstairs area is home to a wood-fired pizza oven, oyster bar, juice stall, and kids’ zone with giant Scrabble, pétanque, ping pong, and nautical books, while the breezy rooftop features four different bars, outfitted with love seats and wire-frame stools for taking in the breathtaking bay views. Aussie wines and beers plus fruity cocktails shaken with house-made juice pair with Mediterranean-themed tapas like chargrilled lamb chops and blistered Padrón peppers.
  • 1003 Upper Fort Street
    In the 1850s, a rugged hill overlooking Sydney Harbour was capped with the Sydney Observatory at the behest of English astronomer and clergyman William Scott. What started as a sandstone structure used primarily for time-keeping and navigation developed into an observatory that has been illuminating the southern sky for more than a century. Sydney has much more light pollution today, but the original retractable copper dome does a good job of blocking it out to bring distant constellations and nebulae into view. The resident astronomer will target planets such as Jupiter and Saturn as well as only-in-the-southern-hemisphere sights such as the Southern Cross constellation or the astronomer’s favorite: Jewel Box, a rare cluster of glimmering stars whose different colors reflect distinct ages.
  • The hike from Coogee Beach to Bondi Beach in Sydney, Australia, is one of the best urban paths I have experienced. Although you’re never far from the city, the walk feels quite scenic at times, and the many beaches you come across along the way are all beautiful. Of course, you can always walk from Bondi to Coogee if you find yourself heading in the other direction. Either way, you’ll find yourself at one of Sydney’s top beach destinations. The hike is an easy walk that will include towering cliffs, sandy beaches, public pools, rock formations, parks, and epic vistas along the 6-kilometer trail. You could do the hike in a few hours, but it would be best to allocate at least three hours to fit in a stop at Bronte Beach for lunch or drinks. And if it is a hot day, you’ll want some time for a swim!