Former working-class enclaves reborn as a yuppie and gay paradise. Paddington's Oxford Street is the shopping mecca; Darlinghurst's Victoria Street is the center of Sydney's café culture.
SEE Paddington Markets
Grounds of the Uniting Church, 395 Oxford St., Paddington, 011-61-2/9331-2923, paddingtonmarkets.com.au
Sydney's oldest community market, founded in 1973. Browse at more than 250 stalls laden with jewelry, crafts, and an occasional tarot-card reader. Many of Australia's biggest fashion labels got their start here, including Third Millennium, Lisa Ho, Bracewell, and Paablo Nevada. Open Sat., 10 a.m.-5 p.m.
EAT Bills Café
433 Liverpool St., Darlinghurst, 011-61-2/9360-9631
Casual, cheery spot famous for Bill Granger's heavenly breakfasts of scrambled eggs and ricotta hotcakes with honeycomb butter. Patrons sit at communal tables and flip through dailies and stacks of magazines.
EAT Bistro Lulu
257 Oxford St., Paddington, 011-61-2/9380-6888, bistrolulu.com.au
Lively and romantic spot for beautifully cooked French dishes. Don't miss the chicken-liver parfait and poached pork fillets. Dinner daily, lunch weekdays. Licensed for wine except Sun. and Mon., when you can bring your own ($10 corkage fee).
EAT Fish Face
132 Darlinghurst Rd., Darlinghurst, 011-61-2/9332-4803
Sydney's best fish, all line-caught (no nets) and simply prepared. Arrive early to score one of only six tables. Reservations are accepted for seatings between 6:30 p.m.-7 p.m. After that, it's a free-for-all. B.Y.O. beer only.
EAT Tropicana Caffe
227 Victoria St., Darlinghurst, 011-61-2/9360-9809
Huge salads, filling pastas, and first-rate coffee. Best known as the birthplace of Tropfest, one of the world's largest short-film festivals (tropfest.com): Judges whittle down 600 entries to 16 finalists, and on one Sunday each February the chosen films are screened outdoors for free (check website for schedule).
SPLURGE Buon Ricordo
108 Boundary St., Paddington, 011-61-2/9360-6729
Top chefs from across the city make a beeline to this 18-year-old Sydney institution for a taste. Chef Armando Percuoco's signature dish is fettuccine al tartufovo, or truffled egg pasta. It's prepared at the table, with nothing but cream, Parmesan, pepper, eggs, and truffles. Spectacular service and an extensive wine list don't hurt either. Closed Sun. and Mon.
DRINK Middle Bar
383-387 Bourke St., Darlinghurst, 011-61-2/9331-3100, kinselas.com.au
The slick, first-floor bar overlooking perennially busy Taylor Square used to be a funeral parlor. DJs spinning wicked tunes attract a mixed straight and gay crowd.
DRINK The Victoria Room
235 Victoria St. Level 1, Darlinghurst, 011-61-2/9357-4488
The decor is bo-co (bohemian-colonial, with brocade sofas, velvet chaise lounges, lazy ceiling fans, and flourishing palm trees) and the crowd a little pretentious. The innovative cocktails-the ginger and lemongrass martini, for one-steal the show. Afternoon tea served Sat., 4 p.m.-6 p.m., and Sun., 2 p.m.-4 p.m. From $20.
SHOP Sass & Bide
4/132 Oxford St., Paddington, 011-61-2/9360-3900, sassandbide.com
The flagship store of this well-known Australian label has all the deconstructed couture women crave, from tiny ra-ra skirts to ruffled mock-Edwardian fancies.
16 Glenmore Rd., Paddington, 011-61-2/9361-6291
The menswear answer to Sass & Bide: distinctive clothing that's part surfer, part rocker, part dandy.
PLAY Centennial Parklands
Corner of Oxford and Lang rds., Paddington, cp.nsw.gov.au
The 480 acres are filled with joggers, cyclists, skaters, picnickers, and horseback riders every day of the week. In the summer months, the outdoor Moonlight Cinema screens classics and the latest releases (moonlight.com.au, tickets $11).