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8 Days Discovering Sydney and New South Wales
Sydney is one of the world’s great cities, of course; but its fabled sites and food scene are just part of the city’s undeniable appeal. Another reason why so many visitors fall in love with Australia’s largest city is that the natural beauty of New South Wales is never far away. In fact, you don’t even have to leave the city limits to experience some of the world’s best beaches.  

Venture farther afield and there’s even more to discover. Up in the higher altitudes, you’ll find an environment ripe for produce to flourish—with vineyards, truffle farms, and orchards peppered among the rolling hills. 

This 8-day itinerary uses Sydney as a base to discover some of the gems of New South Wales and the charming wine and fruit-growing region of Orange. The trip even includes a surprise detour at its end—to overnight at an open plains safari-style zoo.
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    Day 1
    Arrive in Sydney
    You’ll land this morning in Australia’s largest city, Sydney. Even though it’s home to more than five million people and offers an impressively cosmopolitan choice of restaurants, museums, and neighborhoods, part of what separates Sydney from other cities is that the great outdoors is always close by. The city is built around an incredible natural harbor, and world-class beaches lie just minutes from the central business district.  

    The rural and natural sides of New South Wales shape life in Sydney in other ways, too. You’ll find the state’s bountiful produce appearing on your plate in leading restaurants (and even in your cocktails), while the grapes grown here become some of the world’s best wines.  

    Sydney has an impressive array of hotel options—from old-school elegance to trendier contemporary options. At the Sebel Pier One, rooms are built on and above the water (with harbor views from many of them), and the décor celebrates Sydney’s maritime heritage. Another waterfront option is the Park Hyatt Sydney, just across the water from the opera house and next to the Sydney Harbour Bridge.  

    From either hotel, it’s a short walk to the Rocks—Sydney’s oldest neighborhood. Wander the cobblestoned lanes and streets before heading to dinner at Henry Deane, a cocktail lounge and restaurant located on the fourth and fifth floors of the Hotel Palisade. You can admire the panoramic views from the floor-to-ceiling windows as you sip on a handcrafted signature cocktail or mocktail, or enjoy a selection from their curated wine list. Shared plates are mostly Mediterranean in inspiration, with some Asian touches.
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    Day 2
    A Day at the Beaches
    Just as Beefeater guards are icons of England, Australia’s lifeguards have become symbols of the country. Once you’re in Sydney, the reasons why will become clear. Much of life here revolves around the beach, and even from the heart of Sydney’s central business district, you only have to travel a few minutes to reach world-famous beaches.  

    Start today with a visit to Bondi, on the eastern side of the city. The town of Bondi has long had a somewhat bohemian attitude and atmosphere, feeling like a remote beach destination instead of a neighborhood within greater Sydney. That laidback attitude is still on fully display, despite Bondi’s international fame. And the beach is truly spectacular—a golden crescent of sand where surfers ride the waves. Bondi is also the home of another icon of Sydney, the Icebergs Pool, where you can swim some laps before posting a selfie on Instagram.  

    Afterwards, head north to Manly Beach by car or ferry (the trip offers excellent views of the Opera House and the Sydney Harbour Bridge). Manly is also impressive—a stretch of sand that extends for almost two miles, with consistent swells that make it especially popular with surfers. But you’ll also find areas suited to swimming, all monitored by lifeguards keeping a watchful eye. To take a dip without battling the current, visit the two rockpools, Freshwater and Queenscliff, at the beach’s northern end. These public swimming pools along the water’s edge were, like many others along the New South Wales coast, constructed when saltwater swimming became popular. You can get a closer look at the marine life near Manly with a snorkeling tour with EcoTreasures. More than 200 different species of fish, invertebrates, and algaes can be spotted along the northern beaches and in the Cabbage Tree Bay Aquatic Reserve.  

    Enjoy a late lunch at one of the many casual spots along the Corso—a pedestrians-only strip connecting the beach and the ferry—before traveling back to central Sydney.
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    Day 3
    Sydney’s Iconic Structures
    If you chose to stay at one of Sydney’s harbor front hotels, you’ve already enjoyed many views of the Sydney Opera House and the Sydney Harbour Bridge over the last two days. Today, you’ll get an even closer look at them. The Sydney Harbour Bridge Climb is a must for many visitors. The bridge, which was completed in 1932, is an engineering wonder—the tallest steel arch bridge and the sixth-longest spanning arch in the world. During the experience (complete with jump suits and harnesses), you’ll learn about the structure, then ascend it and take in sweeping views of the city and harbor. Choose from several different climbs, lasting from 1.5 to 3.5 hours.  

    After you return to solid ground, visit some of Sydney’s museums. The Art Gallery of New South Wales has a number of notable works by European artists, but its most fascinating galleries are the ones focused on Australia’s Aboriginal and Torres Island Strait populations. You’ll see how the landscapes of the continent and the cultures of its original people were translated into fascinating works of art. The exhibits also include pieces by contemporary artists from both of those communities.  

    The Museum of Contemporary Art has an enviable location—right on the waterfront in the Rocks. Start your visit with lunch at the rooftop MCA Café, and then visit the galleries where both international and Australian artists are represented.  

    In the afternoon, head to the Urban Winery Sydney in Moore Park. While later in the week you’ll travel to the vines, today the grapes make their way to you. This urban winery uses the fruits from New South Wales vineyards to create their wines, and during your experience at the Urban Winery Sydney, you’ll learn about the art of blending different varieties and finish the session with your own unique creation. 

    Later, a Sydney Opera House tour provides a behind-the-scenes look at Australia’s most-visited site. The building, with its soaring sails in white, was completed in 1973 and is both an architectural and an engineering marvel. After your tour, have dinner at Bennelong at the Sydney Opera House, which serves classic Australian dishes in one of Australia’s most famous buildings.  

    You could also choose to explore some of Sydney’s neighborhoods. Check out the atmospheric Paddington Reservoir Gardens, a sunken garden built in a former Victorian reservoir; Chippendale’s White Rabbit Gallery, which specializes in Asian art; or Carriageworks, a multi-disciplinary cultural space in Eveleigh.
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    Day 4
    A Harbor Cruise and Neighborhood Walks
    Many different companies offer cruises of Sydney’s harbor, and once you get on the water you’ll see why: It’s an enormous bay with hundreds of miles of coastline. Some stretches are lined with buildings, while others remain undeveloped, giving a glimpse of what this part of Australia may have looked like when English ships first arrived in the 18th century. The harbor is also dotted with islands: Fort Denison, Shark, Clark, Rodd, Goat and Cockatoo Islands. The last on the list was the site of a penal colony; it’s one of 11 locations in Australia that are part of a collective UNESCO World Heritage site covering the English penal settlements.  

    In the afternoon, take a deeper dive into one of Sydney’s neighborhoods. Much of the excitement and energy of Sydney is found in them; each one feels like its own town within the larger city. Surry Hills has long been one of Sydney’s most popular areas, with its laid-back cafes and many boutiques. In recent years, the openings of a number of new hotels and restaurants have made it an even better area to spend a day exploring. Darlinghurst is one of the city’s most culturally eclectic neighborhoods—the center of the city’s lively LGBTQ scene. Potts Point is liveliest at night; its many bars and clubs are concentrated near the newly energized neighborhood of Kings Cross.
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    Day 5
    Drive to Orange
    Say farewell to Sydney (at least for now) and make the roughly three-hour drive to Orange. Sitting beneath Mount Canobolas, an extinct volcano, the rich soil here has helped make this a bountiful region, full of orchards growing apples, pears, and a variety of exotic fruits. Orange has also emerged as one of Australia’s most interesting (if not as well-known) wine regions, producing chardonnay, sauvignon blanc, shiraz, cabernet sauvignon, and other varietals.  

    Established in the 1820s, Orange grew into a small city, thanks to the success of nearby farms and a railway connecting it to Sydney. Today, its population today is around 40,000, and many historic buildings still stand, especially along Byng Street. The Orange Visitor Information Centre has brochures describing the Orange Heritage Trail and the many 19th-century buildings on it. Spend part of the afternoon shopping for unique gifts and souvenirs at stores and boutiques like The Sonic, The White Place, Angus Barrett Saddlery, and Mary & Tex Curious Emporium

    Dine tonight at Lolli Redini, a perennial favorite in Orange, with a menu that draws its inspiration from French and Italian cuisine, as well as regional Australian fare. A common theme of all the dishes is that the chef makes the most of the bounty from local farms and dairies.
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    Day 6
    Tour the Cellar Doors of Orange
    After breakfast, drive to Rowlee Wines & Vineyard, just to the east of Orange. As is true of many of Orange’s wines, what makes Rowlee’s different from those produced in some other regions of Australia is the cool continental climate and the volcanic basalt soil. The Orange region includes some of the highest altitudes in the country, and the wineries here are almost all small operations producing boutique wines. On your visit to Rowlee, you’ll have an opportunity to sample a number of their single vineyard wines, paired with charcuterie and cheeses, or opt for a more substantial meal with the Vine to Table experience. You’ll enjoy a three-course tasting menu, each course paired with a Rowlee wine. 

    Continue on in the afternoon to visit Printhie Wines, another small operation—they began in 1996 with less than 30 acres of vineyards (the winery has grown but still includes only a modest 80 acres of vines). Jim and Ruth Swift—along with their two sons—now produce some of Australia’s best sparkling wines and will be opening a new cellar door at the end of 2020. Like many Orange wineries, Nashdale Lane is home to vineyards as well as fruit orchards and olive groves. They also have glamping sites here, where kangaroos and King parrots will be waiting outside your tent to greet you in the morning; keep it in mind for your next trip.  

    For the next two nights, you’ll be near Dubbo, to the north of Orange, at the unusual Taronga Western Plains Zoo Dubbo in a Zoofari Lodge. You’ll stay in one of just 10 lodges overlooking a savannah at the heart of the Taronga Western Plains Zoo. While you may be expecting kangaroos and koalas, you’ll actually find a little taste of Africa here, with giraffes, zebras, and rhinos right outside your front door.
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    Day 7
    A Day at the Zoo
    With your stay at the Zoofari Lodge comes with VIP access to Taronga Western Plains Zoo, along with African-inspired breakfasts and dinners, free use of bicycles, and exclusive guided tours.  

    Since its founding in 1977, the zoo’s mission has been to provide ample space for animals whose native habitats are threatened—the operation includes 741 acres of land. Animals from five different continents are represented among the species that live at the zoo, from Sumatran tigers and Indian rhinos to African lions and Cape hunting dogs. The zoo is overseen by the Taronga Conservation Society and operated following the highest standards for the care of its animals.  

    If you thought you were only visiting Australia on this vacation, the unexpected stops to see the lemurs on Primate Island and your safaris through the plains of Africa and the jungles of Asia may feel like unexpected bonuses. Taronga also plays a leading role in conservation efforts for Australia’s own animals. The wildlife hospital here, along with the one at Taronga Zoo Sydney, care for some 1,400 animals each year, including koalas impacted by recent wildfires. Along with the animals from around the world that live at Taronga Western Plains Zoo, there are also many endemic to Australia: koalas, kangaroos, platypuses, and other species, from birds to frogs.
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    Day 8
    You’ll have to leave your new four-legged friends behind this morning. If you have time before your flight home, you may want to stop in Mudgee, another of the wine regions in New South Wales, on your way to Sydney. One of Australia’s oldest wine regions, Mudgee is best known for its rich red varieties, though some wineries also produce award-winning chardonnays. With some 35 cellar doors, you’ll have a wealth of choices for a final toast to your Australian adventure.   

    New South Wales has 14 wine regions, and you’ve only had the chance to explore a few highlights of two of them. Sydney has more than 20 beaches, and you also only made it to two. We expect that as you fly home over the Pacific, you might want to get out a map and decide what other stops you in Sydney and New South Wales will be on the itinerary of your next trip.