Brash and beautiful, Sydney sits nestled in the sandstone cliffs overlooking Sydney Harbour, basking in its role as a gateway for travelers, a mecca of culture and a playground for tourists and its 5 million residents alike. Host to the 2000 Summer Olympic Games, the city is feverishly sprucing up, renovating its infrastructure and repairing its image as a rough-and-tumble town.

In some ways, though, the city delights in its “bad-boy” heritage. Though the region was populated for 100,000 years by the Aborigines, captain Arthur Phillips sailed his First Fleet into Sydney Cove in 1788, bearing nearly 1,000 exiled convicts from British prisons. Settled as a colony of the crown and named “New South Wales,” the country grew as more exiled convicts joined free settlers in forming the basis for the community that would become a major financial and cultural center of the Asia-Pacific region.

Today, Sydney abounds with modern interpretations of its colonial past. At waterfront Circular Quay, where Phillips first landed, street entertainers ply their trade along Writer’s Walk, where famous writers’ words about Australia are fixed in the sidewalk with gold medallions.

The Rocks region has evolved in truly contemporary fashion, from the site of Australia’s first permanent European settlement to its current incarnation as a leading shopping venue that offers some of the city’s finest gifts, souvenirs and native crafts. It’s also renowned for great restaurants and cheerful pubs. History continues to abound in adjacent Victorian suburbs, where a stroll through the cobbled streets and alleyways gives a visitor a sense of the former seaport region’s rich colonial past.

Home to the Harbourside dining and shopping complex, the National Maritime Museum and the Sydney AquariumDarling Harbor invites visitors to meander as they enjoy free music and entertainment on weekends. Outlying beaches stretch for miles, and visitors join locals on the sparkling sand.

Vast and blue, Sydney Harbour is truly the city’s jewel, crowned by the Sydney Opera House. Designed by architect Joern Utzon in 1955, the majestic structure seems to say, “Welcome to Sydney. Prepare to be swept away.”

Things to do

Sydney Opera House

Bennelong Point, Circular Quay
(02) 9250-7111

CityAustralia’s most instantly recognized and enduring symbol, the Sydney Opera House appears to sail the harbor on billowing white wings. A world-class cultural center, the Opera House also hosts the city’s symphony orchestra, ballet, dance and drama, and offers free concerts most Sunday afternoons along the outer walk. Hour-long walking tours (A$9 adults, A$6 children) are available on the half-hour, starting at 9 a.m. and ending at 4 p.m. More info

Royal Botanical Gardens

The Domain
(02) 9231-8125
Cost: Free except for special exhibits
Hours: Daily 7 a.m. to sunset

Originally established as a farm by convicts transported to Australia by the First Fleet, the Royal Botanical Gardens is a lush grove of botanical wonders situated beside picturesque Sydney Harbor. A Tropical Center features the exploits of the Venus flytrap and other intriguing tropical plants that live in the glass-house environment (A$5 adults, A$2 children, A$12 family). Pungent plantings populate the Herb Garden. More info

Bondi Beach

Campbell Parade, Bondi
Cost: Free

Pronounced bon-die, this magnificent stretch of sand is Sydney’s most famous beach, the place to see and be seen either from the sand or from one of the many hip cafes across the street. Prepare for a carnival atmosphere as tourists and locals alike flock to Bondi for an anything-goes frolic in the sun.

Art Gallery of New South Wales

Art Gallery Road, The Domain
(02) 9225-1744
Cost: Free, except for special exhibits
Hours: Daily 9 a.m. to 5 p.m.

Featuring some of the finest Australian works, the museum is particularly proud of its display of Aboriginal art. The permanent collection also includes European, Asian and contemporary art and photography, as well as ever-changing special exhibits.

The Australian Museum

6 College Street
(02) 9320-6000
Cost: A$5 adults, A$2 children, A$12 family
Hours: Daily 9 a.m. to 5 p.m.

This natural history museum traces Australia’s rich culture over tens of thousands of years. Its Aboriginal section explores the impact of white society on the first Australians. Other exhibits feature the flora and fauna of Papua New Guinea, native insects and fossils. More info

The Australian National Maritime Museum

Darling Harbor (west)
(02) 9552-7777
Cost: A$7
Hours: Daily 9:30 a.m. to 5 p.m.

Australia’s history is vitally linked to the sea, and the museum explores those connections with its exhibits of antique racing yachts, WWII destroyers and an America’s Cup champion. More info

The Powerhouse Museum

500 Harris Street
(02) 9217-0111
Cost: A$8 adults, A$2 children
Hours: Daily 10 a.m. to 5 p.m.

Housed in the shell of an enormous, abandoned power station, the museum presents more than two dozen exhibits themed around applied art, science and technology. Here, find a whole floor dedicated to steam engines, airplanes, computers and decorative arts. The museum also includes a NASA space station and a 1930s cinema exhibit. More info

Sydney Harbor Bridge

(02) 9247-3408
Cost: A$2 adults, A$1 children for Pylon Tower
Hours: Daily 10 a.m. to 5 p.m.

CityCompleted in 1932, this bridge remains an engineering feat even today. At 1,650 feet, the bridge is the city’s most-revered landmark after the Sydney Opera House. Affectionately called “The Coat Hanger,” the bridge contains 8 vehicle lanes, 2 railroad tracks, a cycleway and a walkway. The southeast column of the bridge contains a museum that documents the bridge’s construction; walk 200 steps up the Pylon Tower for a magnificent view of the harbor and cityscape beyond.

The Sydney Aquarium

Darling Harbor
Cost: A$15.90 adults, A$8 children
Hours: Daily 9:30 a.m. to 10 p.m.

Home to the most extensive collection of Australian marine life, the Aquarium features crocodiles, seals, fairy penguins and platypuses, as well as an enormous collection of sharks that lurk in its Open Ocean exhibit.

Taronga Park Zoo

Bradley’s Head Road
(02) 9969-2777
Hours: Daily 9 a.m. to 5 p.m.
Cost: $15 adults, $38 families

One of the world’s great zoos, Taronga lets its guests visit nearly nose-to-nose with some of Australia’s most spectacular and exotic creatures – native koalas, of course, but also kangaroos, dingoes, Tasmanian devils and wombats. Scary creatures crawl through their Reptile House habitat. A Zoo Pass includes unlimited passages on the scenic gondola that meanders the 75-acre compound. More info

Centennial Park

Oxford Street, Paddington
(02) 9331-5056
Cost: Free
Hours: Daily, but hours change seasonally

A prime spot for athletes and nature-lovers alike, Centennial Park’s 550 acres boast a wealth of wildlife that coexists beside miles of walking, cycling and horse trails. Visitors can picnic while they watch classic films shown at the amphitheater during summer months.

Luna Park

Milson’s Point
(02) 9922-6644
Hours: Rides open weekends and school holidays; call for seasonal hours
Cost: $20-25 adults, $12-17 children for rides

Built in 1935, modeled after Coney Island’s Luna Park and set against the backdrop of Sydney Harbour, this is a loud, brash, in-your-face amusement park that features a variety of classic rides. Visitors enter beneath the ghastly, grinning face of a painted clown, who has evolved alongside the park’s collection of attractions.

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