Australians have earned their reputation for embracing good times and new adventures. It seems to be part of the national character to surf, swim, and explore the vast natural spaces of the continent. If the idea of a holiday that involves climbing bridges, trying your hand at surfing, and driving along one of the world’s great scenic routes sounds appealing, then you’ll love this trip to Sydney and New South Wales. And if you believe the best way to end a day of adventure is with a meal of farm-fresh ingredients and world-class wines, even better.
This 8-day itinerary begins in Sydney and includes excursions to its famous beaches and harbor, along with stops at some of its cultural and nightlife destinations. You’ll then continue to the South Coast of New South Wales, home to a small but growing wine region, as well as seaside towns that offer perfect places to observe migrating whales. It all adds up to a perfect sampler of New South Wales, curated for travelers eager to embrace adventure and fun.
While Australia’s borders are currently closed, New South Wales looks forward to welcoming you back soon. For further advice on travel to Australia, visit the country’s Department of Health website.
Itinerary / 8 DAYSPLAN YOUR TRIP
DAY 1Arrive in Sydney
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.
DAY 2A Day at the Beaches
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.
DAY 3Sydney’s Neighborhoods
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.
DAY 4A Harbor Cruise and Cultural Afternoon
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.
DAY 5Drive to Jervis Bay
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.
DAY 6Tour the Cellar Doors of the South Coast
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.
DAY 7The Wildlife of Jervis Bay
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.
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.