You’ll land today in Sydney, Australia’s largest city. The Sydney Opera House, Sydney Harbour Bridge, and the Bondi Icebergs Pool are not only world-famous, but also symbols of Australia. There is, of course, much more to the city. The metropolis by the sea has a cosmopolitan and welcoming atmosphere, a food scene featuring all the cuisines of the world, and world-class galleries and museums. From its many neighborhoods with their local favorites and unique charms to the natural beauty of its incomparable setting, Sydney is a city that rewards travelers who want to explore it in depth.  

Your first stop, however, will be to check into your hotel and home for the next three nights. In Chippendale, the 62-room Old Clare pays homage to its building’s former role as the headquarters of Carlton & United Breweries. Choose from a cocktail at the poolside rooftop bar or the Clare, a lobby-level bar that was once a student hangout but has now adopted a more stylish look. The hotel boasts two restaurants by chef Clayton Wells, while many other options lie just outside; Chippendale’s dining scene is booming.

Another option, the Little Albion Guesthouse, sits in the trendy Surry Hills neighborhood just to the east of Chippendale. With its location between Sydney’s Central Business District and the eastern suburbs, Surry Hills is an ideal base for exploring the city, while Little Albion is a stylish hotel. The 35-room property is in a former convent, and there are nods to its unusual history throughout the hotel, as well as works by local artists.  

After you’re settled, head out to wander the laneways of the Rocks. This neighborhood alongside Sydney Harbour is where the first European settlers stepped ashore in 1788. Just to the northwest of the Central Business District, its small streets are lined with restaurants, bars, cafes, and boutiques. The survival of its many historic buildings is thanks to the determined leadership of advocates of historic preservation in the 1970s. Stop off at the Junk Lounge for a drink with views of the harbor and the Opera House and enjoy a meal from its Asian-inspired menu. There are dozens of other excellent options in the Rocks. Local favorites include the Hotel Palisade, Quay, and Saké Restaurant and Bar.

Sydney’s history is tied to the sea—its remarkable natural harbor is, after all, why the British first established a settlement here. And the city’s culture is also focused in large part on its waterfront and beaches. Few of the world’s great cities can also boast that some of the world’s best beaches are literally minutes from their downtowns.  

While Sydney has more than 30 beaches, two in particular—Manly and Bondi—stand out. You’ll grab a beach towel and sunscreen and visit them today, starting at the more distant of the two, Manly. It’s a half-hour drive north of the city; you can also get there on an even more appealing ferry ride. They depart from Circular Quay, next to the Rocks, where you went exploring the previous night.  

Once you arrive at Manly, a stroll along the pedestrians-only Corso will bring you to the beach, with people-watching opportunities and street entertainers en route. The triangular-shaped Fairy Bower Sea Pool is one of Sydney’s most charming sea pools; its breakwaters were constructed when saltwater swimming became popular. History buffs will want to visit Q Station, once a quarantine station for immigrants arriving to Australia and reborn as a luxury hotel. 

In the afternoon, you’ll have a chance to explore an Australian winery—without even leaving the city. Urban Winery Sydney, in Moore Park, is the city’s first urban winery. You can enjoy a typical wine tasting with food pairings in the tasting room—or “cellar door,” to use the Australian term. You can even try your own hand at being a winemaker as you learn to blend your own unique creation.  

When you continue on to dinner, try not to upstage the sommelier with your new knowledge of the wines of New South Wales. Fred’s, on nearby Oxford Street, focuses on farm-to-table preparations of European-inspired dishes (and has a decidedly vegetarian-friendly menu). 10WilliamSt, just off of Oxford, specializes in Italian fare.

Much of what makes Sydney appealing is its individual neighborhoods—each of which has its own energy and atmosphere.  

Start your day by visiting famous Bondi Beach, about five miles east of the CBD. Bondi Beach’s wide, golden crescent of sand is popular with surfers, while the Icebergs Pool overlooking the ocean must be among the world’s most Instagrammed swimming pools. Guests can take a dip for a small fee, and there’s a café there as well. Other lunch options in Bondi include Bondi Beach Public Bar, North Bondi Fish (a casual seafood option), and SHUK, if you’re in the mood for Mediterranean.  

Paddington, which sits to the southeast of central Sydney, rewards travelers who want to take a deep dive into the design, fashion, and food scenes. Its main commercial strip, Oxford Street, features welcoming pubs and cafes, designer boutiques, and a wealth of historic colonial-era buildings. It’s especially charming when the jacaranda trees bloom in October and November, but thanks to Sydney’s mild climate, there’s no bad time of the year to visit. At the place where Glenmore Road and Oxford Street meet, opposite the historic Victoria Barracks, The Intersection includes shops from many of Australia’s top designers. If your Paddington visits falls on a Saturday, Paddington Markets is a showcase for artisans and designers at the beginning of their careers. You may find a unique piece by someone poised to become the next big name in the world of fashion.  

Those interested in contemporary Australian art will want to drop in at the studio of Brett Whitely, the celebrated expressionist painter who died in 1992. You’ll see his workspace much as it looked like when he lived and painted there from 1987 until his death. Temporary exhibitions feature selections of his paintings, drawings, sculptures, and other works.  

In the evening, head west to another one of Sydney’s neighborhoods, Newtown, to experience some of the city’s best pubs and nightlife. You’ll find a wealth of choices along Newtown’s main drag, King Street. Among the local favorites are the Newtown Hotel (its beer garden is an ideal place to spend a warm evening); the Botany View Hotel (for live music); and the Union Hotel (for its long menu of beers). Or try She Loves You, an unusual wine bar. There’s no menu per se; instead, just start chatting with the bartender and he or she will suggest a wine that perfectly suits your taste and mood.

Today you’ll travel to Port Stephens, roughly three hours north of Sydney on the coast. The enormous Port Stephens harbor is larger than Sydney’s, and yet the area is relatively unpopulated. The harbor has more than 20 beaches, as well as small villages on the water’s edge.  

One of the main draws of the area is its resident bottlenose dolphins. More than 140 of them live here year-round, while humpback whales can be spotted swimming offshore during their annual migration from May to November. Dolphin and whale-watching excursions make it possible to get a closer look at both marine mammals. If you want to swim alongside them, Dolphin Swim Australia, in the village of Nelson Bay, is the only wild dolphin swim in the state.  

Afterwards, meet some other Australian residents at the Port Stephens Koala Sanctuary, which includes an operating room, four intensive care units, and a viewing area that houses around 30 of the marsupials.

There’s a wide array of accommodations in Port Stephens to choose from when you book your stay, from glamping to apartment rentals. If you want to stay in style, the waterfront Anchorage Hotel & Spa has rooms that combine Hamptons chic with Australian touches, and all have private verandas or other outdoor spaces.

You’ll have another day to explore Port Stephens today. In the morning, head to Tomaree National Park, at the tip of the peninsula that runs along the south side of the harbor. The park is crossed by trails; the one to the Tomaree Head Summit rewards hikers with stunning views of the sea and some of the settlements nearby. A less-strenuous option is to stroll along the park’s beaches, keeping your eyes open for koalas on dry land and migrating whales just off the coast. The park is also home to several historic buildings, including the 1862-era Port Stephens lighthouse and Fort Tomaraee, built to protect the area during World War II.  

Head to lunch at Bannisters Port Stephens, a hotel sitting on a point extending into the middle of the harbor. The Terrace Bar serves Australian-Mediterranean fusion dishes, while the Cheeky Dog has a casual pub menu (their pizzas are especially popular). At both restaurants, the dishes are paired with views of the harbor. There’s also a fine dining option, Rick Stein, which is open for lunch on Friday, Saturdays, and Sundays. A Hunter Valley Semillon pairs perfectly with their fresh oysters. If you want to enjoy a glass of one of the region’s shirazes at lunch, a hamburger or a grilled steak is a good choice. 

After you’ve recovered from your morning walk, head to one of Port Stephens’ most spectacular sights. The Stockton Sand Dunes run for 15 miles along the coast, are a half mile wide, and reach heights of more than 150 feet. It’s possible to explore the sand dunes on ATV tours with the Aboriginal owned and operated Sand Dune Adventures—learning about the Worimi people is part of the experience when you visit the dunes with them. You can also go sandboarding and experience the thrill of sliding down the dunes on a board.

After a morning in Port Stephens, drive inland today to the Hunter Valley—the most-visited wine region in New South Wales. It’s also the oldest of Australia’s 65 wine regions—the first vines were planted here in 1823 and some wineries have been operating since the 1860s. The area’s warm climate is perfect for travelers; it’s also ideal for Chardonnay, Shiraz, and Semillon grapes. The area’s natural beauty completes the scene with its rolling hills, the Great Dividing Range running along three sides, and the Hunter River making its way along the northern part of the valley.

Hunter Valley’s excellent wines have impressed critics for more than a century—a sparkling wine produced here was described as “equal to the finest champagnes” when it was presented at the Paris Exposition of 1855. The region’s winemakers today continue to be leaders in innovation, with the current generation adopting new styles, varieties, and techniques in pursuit of excellence. By most measures, the Hunter Valley is a relatively small wine-growing region, but the 100 vineyards and 150 wineries here are famous for pursuing quality over quantity.  

Hunter Valley’s reputation for excellence extends beyond wines. It has also emerged as a culinary destination, with restaurants that take advantage of the bounty of produce from New South Wales’ many farms. You’ll dine tonight at one of the most celebrated restaurants in the region, Muse, at the Hungerford Hill Winery. The seasonal menus draw on the best of local suppliers and embrace a contemporary take on Australian cuisine. No wonder Muse has been awarded two chef hats every year since 2015 by the Good Food Guide and it regularly appears on lists of Australia’s best restaurants.  

Once sated, return to your hotel, the Château Élan at The Vintage Hunter Valley. Its spacious suites, manicured grounds, and world-class spa make it one of the Hunter Valley’s most luxurious resorts.

After a leisurely morning enjoying the amenities of the Château Élan, head out today to explore the Hunter Valley’s wineries and vineyards. At the Audrey Wilkinson Winery, you can taste wines during a picnic among the vines.

One of the things you can learn about there is ungrafted old vines. Beginning in the 1850s, an aphid-like insect, phylloxera, destroyed many of the vines of both America and Europe. The solution in those areas was to graft new vines onto old roots. But this step wasn’t necessary in the Hunter Valley, which never felt the effects of the insect. Today, these pre-phylloxera vines produce a lower volume of grapes, but also a more complex and sophisticated flavor. 

The Wilkinson family first purchased the land where the winery is located in 1866, and Audrey Wilkinson became famous as a leading winemaker who helped to develop technology like steam-powered crushers that would be adopted by wineries throughout the country. Though Wilkinson died in 1962, the winery that bears his name continues to produce some of Australia’s most awarded wines. It’s especially known for its Semillon—the single largest variety of wine grapes grown in the area (though Shiraz, Chardonnay, and Verdelho also account for large percentages of the Hunter Valley’s production).

After your delicious picnic among the scenic vineyard, stop at the onsite museum covering the history of the Wilkinson family and their passion for producing fine wines before you continue on your way. Note that the Audrey Wilkinson winery also has three guest cottages, another excellent and intimate option when picking a place to stay in the Hunter Valley.  

In the afternoon, make your way to some of the 150 other cellar doors, or tasting rooms, nearby. At Tyrrell’s, you can try shiraz made from the oldest producing vines in the Hunter Valley. Bimbadgen produces a delicious sparkling variety of Semillon, the valley’s signature wine, and Harkham Wines’ Chardonnay is an excellent example of the natural and preservative-free approach typical of many wineries here. Tulloch Wines’ Mystery Wine Experience puts a fun spin on the typical tasting. You’ll sample six different wines and then attempt to identify the specific varieties or blends. Whichever wineries you visit, you’ll likely want to purchase some bottles so you can recall your days among the vines once you’re back home.  

Dine tonight at Bistro Molines, with a menu and atmosphere reminiscent of the South of France, or Margan Restaurant, where menus are built around whatever ingredients are at their peak in the one-acre kitchen garden. If neither of those exactly suit your mood, there are some 60 other restaurants to choose from in the valley.

Enjoy another morning at the Château Élan, perhaps squeezing in a spa treatment before saying goodbye to the kangaroos that often gather on the grounds. Pack your wine bottles and any gifts from your days in Sydney and begin the journey home. You’ve had only had a small taste of the best of Sydney and New South Wales, and we expect you’ll be returning soon to continue your own extended experience among the vines.