Sydney: The City
Also known as the CBD (central business district), this downtown area is Sydney's commercial and historic heart. It's the home to the harbor and opera house, and is lined with ritzy restaurants.
5 Cumberland St., 011-61-2/8274-7777, bridgeclimb.com
Guided climbs to the top of the Harbour Bridge, eight times daily from 8 a.m. to 5:30 p.m. Twilight tours are the most spectacular, as the sun sets and city lights come on. Allow three hours for the hike, including an information session and breath test. (Alcohol readings over 0.05 will exclude you from the climb.) It's a surprisingly gentle walk, and perfectly safe, but don't even think about it if you don't have a head for heights. From $125, from $75 kids 12-16.
SEE Fort Denison
Sydney Harbour National Park, 011-61-2/9247-5033, nationalparks.nsw.gov.au
A guided visit to this tiny, fortified island includes a tour of the 1862 Martello Tower (fab views) followed by brunch or an optional lunch at the Blue Rock Cafe, Sydney's only island restaurant. Book ahead: Tours are popular and numbers limited. They depart from Cadman's Cottage (110 George St., The Rocks) and last two to three hours. Lunchtime tour Wed.-Sun. at 11:30 a.m and 2:30 p.m., $17 (bring a picnic, or buy food at the café); weekend brunch tour at 9 a.m. $36, including meal.
SEE Government House
Macquarie St., 011-61-2/9931-5222, hht.net.au/museums
A Gothic Revival mansion on the headland above the opera house, converted into a museum devoted to colonial history. Many of the guides are former staff members for the New South Wales governors who once lived here. Fri.-Sun. Free.
SEE Queen Victoria Building
George and Market Sts., 011-61-2/9264-9209, qvb.com.au
An ornate, 19th-century pile built to honor England's (and Australia's) queen at the time, it's now the grandest mall in town. You don't have to shop to appreciate the architecture. Daily guided tours at 11:30 a.m. and 2:30 p.m., $7.50.
SEE Sydney Opera House
Bennelong Point, 011-61-2/9250-7777, sydneyoperahouse.com
Ambling around the spiny exterior is free, but getting inside costs $18 for a basic tour. The two-hour backstage visit takes you to typically off-limits areas, like the orchestra pit, dressing rooms, and the stage, and includes breakfast ($108). Tickets to performances start at about $40 and are rarely discounted; performance packages (tour, dinner, tickets) start at $180. If you're desperate to see a sold-out show, hang around the box office that night and pester the attendants for any returned tickets.
EAT Bambini Trust Café
St. James Trust Bldg., 185 Elizabeth St., 011-61-2/9283-7098, bambinitrust.com.au
For a completely different taste of Sydney, immerse yourself in the pure European charm of this café's dark-wood-and-tile interior. The old-school Italian menu includes pastas and risottos, asparagus and prosciutto, wonderful wines, and strong coffee.
EAT Café Sydney
Customs House, 31 Alfred St., 011-61-2/9251-8683, cafesydney.com.au
Savor some of the finest Sydney rock oysters, plus varieties from the Pacific coast, paired with waterfront views from the roof of the former colonial tax collector's headquarters. Look up through the glass roof of the bar for awesome views of the city's skyscrapers. Lunch only on Sun., live jazz on Fri. nights.
EAT Flying Fish
19-21 Pirrama Rd., 011-61-2/9518-6677, flyingfish.com.au
The city's hottest waterfront restaurant. Stunning interiors feature a surreal "Reef Spawn" resin light sculpture and a towering wall studded with wine bottles. The decor and chef Peter Kuruvita's deft hand ensure it's always hopping, so book way in advance. Dinner only on Sun., closed Mon.
TIP: Waterfront Dining If you're planning a romantic splurge at Wildfire Restaurant (011-61-2/8273-1222, wildfiresydney.com), or any of the other new restaurants inside the Overseas Passenger Terminal, bear in mind that the terminal is also home to visiting cruise liners. Check to see if any of the big ships are in port by consulting Sydney Ports (011-61-2-9296-4800, sydneyports.com.au), taking a harbor stroll, or inquiring with the restaurant when making a reservation. You don't want to miss a picture-perfect view.