Nestled between William and Oxford Streets, East Sydney was once a dairy farm and market garden. Nowadays this diverse conservation area is best known for its pubs, fantastic Stanley Street, ‘Little Italy’ restaurants, and the Australian Museum.

Darlinghurst was formerly known as Eastern Hill before it was named as we know it today after NSW Governor Ralph Darling. Famous for its 1841 gaol, now the National Art School, and the Darlinghurst Court House, built in 1835. Darlinghurst was formerly known as Eastern Hill.

Shopping
The areas main shopping strip is Oxford Street, stretching from Hyde Park to South Dowling Street. Here you’ll find everything from clothing boutiques, late-night book shops and music stores to supermarkets, gourmet food stores, homeware outlets and gift shops. Oxford Street buzzes day and night. You can pop into one of the many pubs, bars or clubs for a leisurely drink or spend your time viewing and/or purchasing artwork at one of the many galleries scattered along the strip.

Dining
Oxford Street is well known for its low-priced restaurants, including Thai, Indian and Spanish, or head to nearby Stanley and Crown Streets for a great selection of Italian cafes and restaurants.

Another good option is buzzing Victoria Street, Darlinghurst. This area is famous for its coffee and Italian-style cafes, but there are also some good Indian and Thai restaurants to sample. Neighbouring Darlinghurst Road and Liverpool Street also have a variety of restaurants to choose from.

* Information source City Of Sydney Council *

Originally a prestigious address where the wealthy built their villas, such as Elizabeth Bay House, Kings Cross later became the haunt of bohemian artists and writers and a ‘rest and recreation’ destination for servicemen. Today, ‘The Cross’, along with neighbouring Potts Point and Elizabeth Bay, is Australia’s most densely populated district – a famous nightlife and dining area and a magnet for tourists and locals. Down the hill, the once working-class area of Woolloomooloo contains delightful terrace houses and the Finger Wharf, now transformed into a glamorous hotel, dining and apartment complex.

Shopping
The best shopping strip is Macleay Street, Potts Point. This location consists of an array of delectable delis and food stores to choose from, clothing boutiques, homewares and a major supermarket. Elizabeth Bay Road offers a delicatessen, upmarket boutique and bottle shop. Other supermarkets and convenience stores are located in Kings Cross and Woolloomoolloo, and don’t forget the local Sunday market, held in Fitzroy Gardens – a great place to find new age items, second-hand goods, books and crafts.

Dining
There are over 200 bars, restaurants and cafes in the area, particularly around Darlinghurst Road, Macleay Street, Bayswater Road and Kellett Street, as well as leafy Victoria Street in Potts Point. Woolloomooloo also has some good options, sample a famous pie floater at Harry’s Cafe de Wheels (open until late every night) or enjoy affordable pub food, seafood, steaks, Asian dishes and modern Australian cuisine at the fabulous waterfront wharf complex.

* Information source City Of Sydney Council *

As one of Sydney’s more illustrious suburbs, modern Paddington is a mecca for trendy shoppers and diners and well known for its markets.

The first cottages were built around the 1840s Victoria Barracks Army base, and the area is still famous for its charming terraced houses and other National Trust listed architecture.

South of Oxford Street is the small leafy suburb of Centennial Park and the Moore Park precinct, containing two of Sydney’s great sports grounds, the SCG and Aussie Stadium, and The Entertainment Quarter, formerly Fox Studio.

* Information source City Of Sydney Council *

 Moore Park & Centennial Parklands

Escape to the wide-open spaces of Centennial Parklands for everything from cycling to horse riding, roller blading, tennis, golf, netball, cricket, ranger programs, barbecues and picnics – or to simply soak up the fresh air and sunshine.

Be part of the excitement of big-time sport and entertainment at Moore Park, which includes the Sydney Cricket and Aussie Stadium, featuring Australian Rules Football, cricket, Rugby League, Rugby Union, football (soccer), concerts and interactive venue tours.

Shopping
The buzzing thoroughfare is at its best on Saturdays, when the long-running Paddington Markets feature dozens of stalls offering clothing, gourmet foods, plants, books and handcrafted goods, as well as live entertainment and delicious food.

The Entertainment Quarter at Moore Park is an other great shopping area, with late-night shopping, and Wednesday and weekend markets that specialise in produce, clothing and collectables.

Dining
The best restaurants can be found west of Victoria Barracks consisting of many pubs and specialty restaurants. An area that is particularly good for daytime cafes is located east of Paddington Town Hall.

The Entertainment Quarter offers global dining, with over 20 places to eat – from coffee shops to seafood and superb Chinese cuisine.

* Information source City Of Sydney Council *

In the early 19th century, Surry Hills was on the outskirts of the city and the ideal place to build a mansion, but the area later sank into decline, becoming an overcrowded slum, with brothels and notorious gangs – as described by Ruth Park in her 1940s novels, Poor Man’s Orange and The Harp in the South.

Today’s Surry Hills, and neighbouring Strawberry Hills, is a very different place – a colourful and diverse inner-city suburb that is well known for its art galleries, antique dealers, cafes and pubs, and fashion and rag trade outlets.

Shopping
The focus of Surry Hills shopping is busy Crown Street, popular for its off-beat clothing, homewares and collectables, bookshops and food outlets.

On the first Saturday of every month, the Surry Hills Market is held at Shannon Reserve. This is a great place to find clothing, gifts, creative crafts and bric-a-brac.

Also in the area is the excellent Sydney Antique Centre on South Dowling Street, and Cleveland Street’s Surry Hills Shopping Village, ideal for every day shopping.

Dining
There is an extraordinary range of eateries on Crown Street, from tiny Lebanese and Turkish takeaways to upmarket modern Australian restaurants and some excellent pub dining rooms such as the Dolphin, Clock and Hopetoun, offering meals at very reasonable prices. Oxford, Riley, Albion and Bourke Streets also feature many places to eat, including some good Asian and Italian establishments.

Prince Alfred Park
Located just south of Central Station, Prince Alfred Park is best known for its 1950s-style outdoor swimming pool. Spanning more than 7.5 hectares, this vital community park also features large grassed areas, a playground and tennis courts.

Shannon Reserve
This park at the corner of Crown and Collins streets is the location of the Surry Hills Market – held on the first Saturday of every month, subject to weather.

Hills Reserve
Hills Reserve at the corner of Albion and Riley Streets was once a gully known as ‘Frog Hollow’. Filled to the brim with narrow terraces that were overcrowded and had poor light and ventilation, it was a notorious ‘no-go area’ frequented by some of the area’s worst criminals in the 1920s. The council is currently redeveloping the site for more extensive use.

* Information source City of Sydney Council *