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 NSW 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 historic elegance to trendier contemporary options. At Pier One Sydney Harbour, plush rooms are built on and above the water (with harbor views from many of them), and the décor celebrates Sydney’s maritime heritage. Another luxurious harborside stay is the sleek Park Hyatt Sydney—favored by celebrities, it has unrivalled views of Sydney Opera House and personalized service.

From either hotel, it’s a short stroll to the Rocks—Sydney’s oldest neighborhood. Wander the cobblestoned lanes before heading to dinner at Henry Deane, a cocktail lounge and restaurant located on the top two floors of the chic Hotel Palisade. 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 Mediterranean in inspiration with some Asian touches, and you can even stay the night upstairs in their heritage-style boutique suites.

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 surf beaches and sandy harbor coves.

Start today with a visit to Bondi, on the eastern side of the city. The precinct 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 full 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.

One of the best ways to soak up the ocean views is by strolling from Bondi to Coogee on the spectacular coastal walk. You’ll wind past sandstone cliffs, tempting Tamarama beach (known as Glamarama or Tama to locals) and plenty of cafes and restaurants. A little further along is European-style Clovelly Beach, with a concrete-edged sea channel where locals sunbathe, drink takeaway coffees and jump into clear waters for a snorkel. Back in Bondi, if you want to try surfing on one of the globe’s most famous beaches, Lets Go Surfing are a friendly, experienced team of instructors who will have you standing up in no time—they are also the only officially licensed surf school on Bondi Beach.

Enjoy a long lunch with superb ocean views at Icebergs Dining Room and Bar—along with an impressive menu inspired by regional Italian cuisine, this sleek, sun-filled space has one of the most spectacular outlooks of any restaurant in the world where you feel like you are sitting high above the blue ocean. At the other end of Bondi Beach you’ll find North Bondi Fish, a relaxed beachfront seafood eatery with a vibrant atmosphere, weekend DJs, and botanical cocktails.

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 BridgeClimb 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 jumpsuits 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 tomorrow you’ll venture to the vines, today the grapes make their way to you. This inner-city winery uses fruits from NSW vineyards to create their wines, and during your experience at the Urban Winery Sydney, you’ll learn about the art of blending different

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 enjoy fine dining at Bennelong inside the soaring Opera House sails. The menu matches the magnificence of the space with innovative, flavorsome creations championing some of Australia’s top food and wine producers.

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 Chinese contemporary art; or Carriageworks, a multi-disciplinary cultural space in Eveleigh.

Say farewell to Sydney (at least for now) and make the roughly three-and-a-half hour drive to the country town of Orange in the Central Tablelands region of NSW. 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) cool-climate wine regions, producing Chardonnay, Sauvignon Blanc, Shiraz, 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 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. A little further afield in the heritage-listed village of Millthorpe, a short 15-minute drive from Orange, Tonic is a one-hat (similar to one Michelin Star) restaurant serving classic dishes with a modern twist, using seasonal, local produce including Mandagery Creek Venison and Cowra Lamb.

Breakfast in Orange is acclaimed with plenty of innovative twists on classic dishes. Just nearby, Byng Street Local Store has a dedicated brunch menu on Saturdays and Sundays with favorites including Croissant with bacon, avocado and spicy almond relish, and poached eggs with sage and parmesan. Over at The Greenhouse, the menu spans everything from buttermilk pancakes with hazelnut crumble to signature cocktails garnished with kitchen garden herbs. For excellent coffee and feel-good food-on-the-go like toasted sandwiches and strong espresso, head to the minimalist coffee bean roasting house, Good Eddy.

After breakfast, drive to Rowlee Wines, 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, who produce some of Australia’s best sparkling wines. Established by the Swift family in 1996, Printhie is now run by brothers Ed and Dave Swift and the winery will open a new cellar door and restaurant in 2021. Not far away, discover Nashdale Lane, a family-owned vineyard with two inviting glamping tents available for lodging. The wooden, steel, and canvas tent structures have a distinctly Aussie flavour and are rustic yet luxurious.

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.

Today you are heading to Dubbo to the north of Orange and for the next two nights, you’ll be staying 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, too, with giraffes, zebras, and rhinos right outside your front door.

Your stay at the Zoofari Lodge comes with two days 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 breathtaking 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 bushfires. 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.

You’ll have to leave your new four-legged friends behind this morning. Stop in Mudgee, another award-winning wine region in NSW for your last night. Mudgee is just about a two-hour drive from Orange, then a three-and-a-half hour drive or 55-minute flight back 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.  

Don’t miss Logan Wines, where the architecturally designed tasting room is all glass and light, bringing the countryside in. Sit and savor their Clementine Pinot Gris, named after winemaker Peter Logan’s daughter. Next, linger over a locavore lunch with vineyard views at Lowe Wines. There’s a cellar door proffering organic and biodynamic wine and Zin House serving food that captures the spirit and ingredients of the surrounding gardens and farmlands. Stay tonight in one of the most unique accommodation offerings in the region, Sierra Escape with five-star glamping tents that boast king or queen beds and polished timber floors—two even have deep freestanding baths.

As you make your way back to Sydney to catch your flight home, consider that New South Wales has 12 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 Bondi. 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 when you return.