You’ll land today in Australia’s largest city, Sydney. With its sunny attitude and the warm welcome extended by Sydney residents, you might not expect it’s a city with a secret side. But dig deeper and you’ll find surprises at every turn. This itinerary is designed for travelers looking not only to view a new corner of the world, but also try some unexpected adventures.  

That begins with your hotel in Sydney. The city has no shortage of five-star hotels from familiar brands, but it also features some unique options you’ll find nowhere else. Ovolo Woolloomooloo, for example, is located in a former wool warehouse right in the center of the city, on a pier between the Royal Botanical Garden and Pott’s Point. The industrial building has been renovated and repurposed as a stylish hotel filled with contemporary art and whimsical touches. Another option: The Lord Nelson Brewery Hotel, where you can sleep in a pub that has been operating since 1841. Or try the Watsons Bay Boutique Hotel, a cool beach club near the entrance to Sydney’s harbor. It’s roughly a half hour by car from the central business district, but not many hotels let you combine a big-city getaway and a beach vacation in one stay.  

Start your exploration of Sydney where the city itself started—the Rocks. This neighborhood of 19th-century buildings in the heart of contemporary Sydney may feel surprising. The Rocks’ survival into the 21st century is the result of the tireless advocacy of historic preservationists and some far-sighted policy decisions in the 1970s. Its cobblestoned laneways are popular with visitors, but there are still some spots that manage to remain insiders’ secrets. Ragazzi is one: a tiny Italian restaurant tucked away on a back street, Angel Place. It opened at the end of 2019 and has quickly found a loyal following. Restaurant Hubert opened in 2016, but with its speakeasy ambience, it feels like a long-running underground institution.

It may be Australia’s largest city, but Sydney feels like a resort destination when you head to its beaches. The city has more than 20 sandy stretches, and you’ll see the two most famous ones today. Start with spectacular Bondi, on the city’s eastern side, where a number of beachside schools can help anyone looking to ride a few waves and experience Australian surf culture. Swimmers can brave the surf or drop by the iconic Icebergs Pool, at the beach’s western end. If time allows, the four-mile Bondi to Coogee Coastal Path boasts jaw-dropping ocean views. (You can also just walk a portion of it, stopping at Bronte Beach.)

After you’ve seen Bondi, continue on to gorgeous Manly Beach, the most common gateway for visitors to Sydney’s northern beaches. It’s often described as the birthplace of surfing in Australia, after the sport was permitted here beginning in 1903. It remains a popular surfing destination with its consistent swells, while the pedestrians-only Corso is ideal for both people-watching and grabbing a quick lunch. Banana Blossom Manly, right on the Corso, is a favorite for Asian-inspired salads. The Boathouse Shelly Beach, to the south of Manly Beach, serves seafood favorites as well as one of Australia’s most successful culinary exports, avocado toast. At the first beach north of Manly, Pilu at Freshwater serves Sardinian dishes by the sea.

In Sydney, you’ll find much of the city’s excitement and energy in its various neighborhoods, which offer a lot to explore. In Paddington, for example, the Paddington Reservoir Gardens is an area of landscaped Romanesque-style ruins built in a former reservoir that’s been restored into an unusual grotto. Enjoy lunch at the Unicorn Hotel, which serves excellent renditions of Australian comfort foods, from onion dip to prawn cocktails—just leave room for pavlova for dessert.  

Paddington is also where many of Sydney’s top galleries are located, with works that are often challenging and daring. The focus at Blender Gallery is on music photography, with exhibits featuring artists who have captured the stars of rock, pop, and other genres on film. The UNSW Galleries regularly feature exhibitions that question our definitions of art, with performance pieces, video installations, and works that incorporate archival images and other found materials.  

To the southwest of central Sydney, Newtown has emerged in recent years as one of the city’s liveliest neighborhoods, with a mix of hipsters, students, and a significant LGBTQ community. The Enmore Theatre is one of Sydney’s premier spots for musical acts, and although Carriageworks is just outside Newtown, the multi-disciplinary cultural space’s exhibits and performances justify the detour. King Street is the main nightlife strip, with popular bars including the hip Newtown Hotel and the Courthouse Hotel (just off of King on Australia Street), which is still going strong after a century in business.

Get out on the water this morning with a sail around Sydney’s harbor—an enormous bay with hundreds of miles of coastline. Mansions come down to the water’s edge in some places, while other stretches remain undeveloped, offering a glimpse of what the area may have looked like when English ships first arrived in the 18th century. The harbor is also dotted with islands. One of them, Cockatoo Island, was the site of a penal colony, and before that a meeting place for the Eora people; it’s one of 11 locations in Australia that are part of a collective UNESCO World Heritage site made up of colonial-era penal settlements. Several companies offer sailing cruises, so you can pick the one that best suits your schedule. Many last for about three hours, and your ship’s captain will point out significant sites.  

Later, ascend to new heights on a Sydney Harbour Bridge Climb—a must-do 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. On a climb, you’ll learn all about this amazing structure and then take in the sweeping views of the city and harbor. There are several different climbs to choose from, lasting from 1.5 to 3.5 hours. 

In the afternoon, a visit to one of Sydney’s most famous parks will provide insights into the city’s culture and history, as well as simply being a lovely way to enjoy the blissful climate. The Royal Botanic Garden, founded in 1816, is the country’s oldest scientific institution; thanks in part to the remarkable biodiversity of Australia, it has long been one of the world’s most important botanical gardens. Guided walks offered three times a week—on Wednesday, Friday, and Saturday mornings—provide a different perspective on the garden. On the Aboriginal Heritage Tour, you’ll learn about the plants used by the indigenous Cadigal people and, depending on what’s in season, you may taste some too. Its stunning location on 74 harbor front acres—and the fact that admission is free—make it one of Sydney’s most-visited attractions. 

Don’t linger too long, however—later today you have a wine experience scheduled at the Urban Winery Sydney. You may have assumed that your trip to Australia would include sampling many excellent wines, but you probably didn’t expect that you’d be creating your own wine, too. Here you’ll take a class in how to blend wines and then concoct your own. If you’re pleased with your creation, you can purchase a dozen bottles with your own personalized label. Afterwards, head to nearby Oxford Street, where you’ll find a number of small bistros and brasseries helmed by young chefs.

This morning, drive south from Sydney to Jervis Bay along the South Pacific Ocean. The three-hour trip follows a breathtakingly scenic route, with most of it along Grand Pacific Drive. Near Wollongong, the road is constructed just off the coast and over the ocean—the Sea Cliff Bridge is one of Australia’s most photographed landmarks. Along the way, stop at seaside towns like Kiama, best known for its blowhole and historic terrace houses. It’s just one of a string of appealing coastal towns and cities. And inland, not far from Jervis Bay, you’ll find an impressive collection of 19th-century colonial buildings in the town of Berry. 

At the end of your journey is Jervis Bay, which covers almost 40 square miles. Its coast is ringed by powdery white beaches; keep an eye out for bottlenose dolphins, seals, penguins, and sea birds in the bay, and humpback whales in the nearby ocean (during their annual migration from April to November). You’ll spend the next three nights at Paperbark Camp, where 13 glamping-style tents sit in the shade of eucalyptus and paperbark trees. The luxurious tents have solar-powered lighting, polished hardwood floors, en suite showers, handmade soaps, and other amenities.

After breakfast, explore some of the wineries and “cellar doors”—what Australians call tasting rooms—in the Shoalhaven Wine Region. Of Australia’s 65 different wine regions, Shoalhaven is on the smaller side—there are fewer than 20 cellar doors. As a result, many of the winemakers are especially accessible and eager to greet visitors who are curious about this emerging area.  

One example: Rosie and Griff Cupitt, who planted their first wine grapes in 2005. Cupitt’s Estate now produces excellent sauvignon blancs, rosés, cabernets, and other wines. The estate is also home to a brewery (established in 2014) and a fromagerie, producing goat’s and cow’s milk cheeses since 2015. On their Tour and Taste experiences, you’ll follow a tour that includes the vineyards, cellars, kitchen garden, microbrewery, and fromagerie, with a chance to sample the products from all those different parts of the Cupitts’ estate. You will surely end your visit sated. On your way to Cupitt’s, stop at Milton—an especially charming farm town with historic buildings, craft studios, and antique stores.  

If you don’t have lunch at Cupitt’s, Bangalay Dining in Shoalhaven Heads creates dishes that showcase local ingredients—not only wines, produce, and beef, but also various herbs and flowers. You can choose from the formal dining room or a more casual alfresco lunch. In the afternoon, continue your wine tastings with stops at cellar doors to the north of Jervis Bay, on or near the Shoalhaven River. Coolangatta Estate has a long history—it was the site of the first European settlement in the area, and a number of its buildings were constructed by convicts. Its owners began producing wines in the 1980s, and the estate remains committed to small-scale production practices. Two Figs Winery, just outside Berry, produces shiraz, pinot noir, viognier, pinot grigio, and several other varieties. Mountain Ridge Wines has an inviting cellar door in Coolangatta, while family-run Cambewarra Estate offers afternoon tea as well as wine tastings.

On your last day on the South Coast, get a closer look at the region’s incredible array of marine life. Migrating whales pass by this stretch of coast from April to July (when they’re swimming north) and then again from mid-August to November (when they return south to Antarctica). On a Swim with the Whales excursion, you may even be able to snorkel with them. Your boat will drop you off no closer than 300 meters from the whales, and it’s up to them whether they want to approach. The curious creatures often do, though snorkelers are instructed not to get any closer than 30 meters. It’s an unforgettable close encounter with one of the most majestic animals in the sea.  

Afterwards, enjoy a lunch of one of the sea’s smallest creatures on a visit to the oyster sheds of Greenwell Point. Jim Wilds Oysters and Shoalhaven Oyster Service serve some of the freshest oysters and prawns you’ll ever eat.  

If you’re visiting in the winter or spring, you may want to spend the day visiting the Montague Island Nature Reserve, off of Narooma (just under three hours from Jervis Bay). The populations of Australian and New Zealand fur seals begin to grow in the winter and peak in the spring. During the annual humpback migration, the island is also a good place to observe the whales swimming by.

Today you’ll have to close the flaps on your luxury tent and return to Sydney for the journey home—unless you had the foresight to ask Islands In the Sun to add on more days to visit other parts of New South Wales.  

Every visit to the South Coast offers new perspectives and experiences. If you first visit when the grapes are just emerging on the vines, you’ll likely want to return for the harvest. Similarly, no visit to Sydney is like the previous one, thanks to its busy events calendar and the new restaurants, bars, and exhibits that open every month. As you look ahead to planning another vacation in New South Wales, you’ll now know your way around and be ready to dive deeper into all that the state offers when you return.