High life and low life coexist in this happening peninsula east of the city. Glam homes, bars, and restaurants brush up against Sydney's sleazy side.
SEE Elizabeth Bay House
7 Onslow Ave., 011-61-2/9356-3022, hht.net.au/museums
Once described as "the finest house in the colony," this small museum-originally built between 1835 and 1839 as a home for colonial secretary Alexander Macleay-offers intriguing insights into the early days of English settlement in Sydney. Furnishings are from the period 1839-1845. Closed Mon. $5.30.
EAT Fratelli Paradiso
12-16 Challis Ave., 011-61-2/9357-1744
A busy neighborhood trattoria that does the best fried calamari in town-simply battered, golden, and meltingly tender. The no-reservations policy translates to perpetual lines, but the quick turnover keeps waits under half an hour.
EAT Simmone Logue
21 Elizabeth Bay Rd., 011-61-2/9358-2600, simmonelogue.com
On the ground floor of a smart city apartment block, this is the place to be for "Sunday roast"-a traditional Australian meal of lamb, chicken, beef, or pork (or whatever the chef decides that day), served with crispy potatoes, peas, pumpkin, and carrots, and plenty of rich, thick gravy, as well as pudding and wine. B.Y.O. wine only, $10 corkage fee per bottle.
EAT Spring Espresso Bar
65 Macleay St., Shop 1, 011-61-2/9331-0190
So cramped it's almost uncomfortable, but people flock here anyway for a weekend brunch of scrambled eggs and smoked salmon. The outside tables are less claustrophobic.
6 Cowper Wharf Rd., 011-61-2/9368-7488, otto.net.au
Fine Italian dining by the waterfront, with wines and service to match. The city's elite come to dine in sun-drenched splendor on exquisite pastas and memorable desserts, such as shortbread with mascarpone, strawberries, and Ligurian honey. First-class people-watching, too. (Russell Crowe lives at the end of the wharf.)
5 Roslyn St., 011-61-2/9358-6131
Seedy old Kings Cross may be gentrifing, but this bar hasn't changed a lick. Tacky decor, cheap drinks, open all night.
22 Challis Ave., 011-61-2/9326-0488, merivale.com/lotus
A small but perfectly formed bistro that's part of the burgeoning Hemmes family empire (CBD Hotel, Establishment, Slip Inn, et al.). Its tiny, shiny bar with snakeskin-padded walls serves fine cocktails, including a Rat Pack of martinis (like the Frank and the Dino).
DRINK Water Bar
W Hotel, 6 Cowper Wharf Rd., 011-61-2/9331-9000, starwoodhotels.com
Consistently voted Sydney's best watering hole. It has a unique old-meets-new ambience. The hotel is housed in a former dockside warehouse, with soaring wooden ceilings; glass elevators ferry guests to the rooms, and drinkers recline on sleek divans.
SHOP Il Papiro
87A Macleay St., 011-61-2/9361-6252, ilpapirofirenze.it
The antipodean outpost of an upscale Florentine stationer known for divine marbleized diaries and notepaper with signature feather designs.
PLAY Andrew (Boy) Charlton Pool
1C Mrs. Macquaries Rd., The Domain Sydney 2000, 011-61-2/9358-6686, abcpool.org
Named after a swimming legend from the 1920s. Its location-above Woolloomooloo Bay-ensures it's constantly packed. Open 6 a.m.-8 p.m., Oct. 1-Apr. 30. $3.90.
ESCAPE Royal National Park
The world's second-oldest national park after Yellowstone. The terrain-crisscrossed by myriad trails-varies from bushland to rain forest, craggy coastlines to tranquil riverbanks. And it's easy to reach: Take a train to Cronulla (cityrail.nsw. gov.au, about $6.60 round trip), then catch the National Parks Service's ferry to Bundeena (011-61-2/9523-2990, $7.30 round trip). $7.50 day pass for car, free otherwise.
TIP: Aboriginal Art One of the world's oldest peoples, Aborigines arrived in Australia nearly 50,000 years ago from southeast Asia and fanned out, developing more than 250 regional languages as well as rich, spiritually infused artistic traditions. Today, Sydney's indigenous population numbers over 30,000, and many continue their time-honored crafts. Perennial souvenir favorites include the boomerang-originally used for hunting and fire-making-and the didgeridoo, a wind instrument created from a log hollowed out by termites. Carved and painted emu eggs, bark paintings and dot paintings of animals and plants, woven baskets, and sculptures of creator-beings are also popular. Be aware that opportunistic dealers in fake and illegally appropriated art run rampant. Stick to community arts-and-crafts centers and to galleries owned, operated, or supported by Aborigines, and do some research before you buy (mq.edu.au/house_of_aboriginality).