1 Sydney Opera House. What to say? It's one of the wonders of the modern world and a true Sydney icon. Catch a show if you like, but just gazing up at those sails from the forecourt is still mesmerising. (Even for those of us who live here.)
2 While you're at the House, pop into Opera Bar on the adjoining concourse for in-your-face views of the bridge and harbour. Or, if you're feeling fancy, a glass of Champagne and some crab sandwiches at the bar at Guillaume at Bennelong are just the ticket. Opera Bar, lower concourse, Sydney Opera House, (02) 9247 1666; Guillaume at Bennelong, (02) 9241 1999
3 You still want more? Take an Opera House guided tour - from $28 per person - and for an insider's look, book in for the backstage tour; it's $150 (including breakfast) well spent. (02) 9250 7250
4 Just across Sydney Cove, BridgeClimb now offers three options for clambering up Sydney's other most famous landmark: The Express, The Discovery and The Bridge, from $188. 3 Cumberland St,The Rocks, (02) 8274 7777
5 Down below, Quay is Sydney's finest dining experience, combining exquisite food from chef Peter Gilmore, a compelling wine list and knockout harbour views. (Ask for a table in the tower.) It's our Restaurant of the Year - for the second year in a row. Overseas Passenger Terminal, The Rocks, (02) 9251 5600
6 While you're living the high life, head up to the Orbit Lounge Bar. This 47th-floor revolving bar affords 360-degree views of Sydney. And the Daiquiris aren't half-bad, either. (Pack some Kwells.) Australia Square, 264 George St, Sydney, (02) 9247 9777
7 For views of a different kind, take in the Brett Whiteley Studio, set in the former workspace of this seminal Australian artist. Or, for that matter, any of the masterpieces on show at the Art Gallery of NSW. Make sure you check out the impressive views of Garden Island. Brett Whiteley Studio, 2 Raper St, Surry Hills, (02) 9225 1740; Art Gallery of NSW, Art Gallery Rd, The Domain, (02) 9225 1744
8 Other favourite galleries include the contemporary arts centre Carriageworks, housed in the old Eveleigh Rail Yards, the Tim Olsen Gallery, dominated by the works of John Olsen, and, for craft and design, Object Gallery. Carriageworks, 245 Wilson St, Eveleigh, (02) 8571 9099; Tim Olsen Gallery, 63 Jersey Rd, Woollahra, (02) 9327 3922; Object Gallery, 417 Bourke St, Surry Hills, (02) 9361 4511
9 The Museum of Contemporary Art is a big whack of culture right in the centre of Circular Quay (even if you spend half your visit at the gift store), and it's free. MCA, 140 George St, West Circular Quay, (02) 9245 2396
10 Check out home-grown talent at local theatres such as SBW Stables or Darlinghurst theatres, or combine culture-vulturing with a crisp beer at The Old Fitzroy, Woolloomooloo's pub-cum-theatre. SBW Stables Theatre, 10 Nimrod St, Kings Cross, (02) 8002 4772; Darlinghurst Theatre, 19 Greenknowe Ave, Elizabeth Bay, (02) 9331 3107; The Old Fitzroy, 129 Dowling St, Woolloomooloo, (02) 9356 3848, tickets 1300 438 849
11 And the hottest ticket in theatre town? Anything at the Sydney Theatre Company, under the direction of Cate Blanchett and Andrew Upton.
12 Forget tight-wallet Tuesdays at faceless cinema chains and check out $13 movie tickets every day ($8 on Tuesday) at the fabulously kitsch Randwick Ritz. The popcorn's pretty good too. If independent cinemas tickle your fancy, have a look at the Hayden Orpheum in Cremorne. Randwick Ritz Cinema, 45 St Pauls St, Randwick, (02) 9399 5722; Hayden Orpheum, 380 Military Rd, Cremorne, (02) 9908 4344
13 Still on the silver screen, grab a cushion and catch a movie under the stars: St George Open Air Cinema at Mrs Macquarie's Point, Moonlight Cinema at Centennial Park; Starlight Cinema at North Sydney Oval; and Bondi Open Air.
14 To get a real feel for the city, get out on the harbour. And do it with class, aboard a luxury heritage-style yacht, like the gracious Southern Cloud. Or think green and explore the city's waterside suburbs by hopping on a ferry.
15 One of the best ways to see the harbour is on foot. Try the walk from Taronga Zoo to Balmoral, stopping for lunch at The Tea Room Gunners' Barracks or Serge Dansereau's Bathers' Pavilion along the way. Or skip the walking and just head down to Bathers' Pavilion for one of Sydney's best-loved breakfast spots. Taronga Zoo, Bradleys Head Rd, Mosman, (02) 9969 2777, taronga.org.au; The Tea Room Gunners' Barracks, end of Suakin Dr, off Middle Head Rd, Mosman, (02) 8962 5900; Bathers' Pavilion, 4 The Esplanade, Balmoral, (02) 9969 5050
16 Walking from The Spit to Manly takes in Grotto Point Lighthouse and Crater Cove lookout, and when you get to Manly itself you can… Have a beer at the Manly Wharf Hotel or sip a cocktail with the northern beaches' hot young things at Hugos Manly before hopping on a ferry to Circular Quay. Manly Wharf Hotel, East Esplanade, Manly Wharf, Manly, (02) 9977 1266; Hugos, East Esplanade, Manly Wharf, Manly, (02) 8116 8555
17 While you're in Manly, check out the board riders on Manly Beach, one of Sydney's premier surf spots. It's not as easy as it looks, but if you're inspired to give it a go, Manly Surf School is one of the most respected in the country. North Steyne Surf Club, Steyne Rd, Manly, (02) 9977 6977
18 Up north a bit, Freshwater is home to one of Sydney's best dining experiences: Pilu at Freshwater, serving authentic (and very delicious) Sardinian fare in a very Aussie beach-house setting. (The suckling pig is legend.) Or for a great alternative, grab a suckling pig panino or coffee from the adjacent Pilu kiosk and wander down to the beach to check out the birthplace of surfing in Australia. End of Moore Rd, Harbord Beach, (02) 9938 3331
19 Bondi to Coogee is the great walk of the eastern suburbs, snaking down from south Bondi to Tamarama beach, past Bronte, along the cliffs by the stunning sight of the Waverley Cemetery to Clovelly, then around Gordons Bay to Coogee Beach - the sea views are nothing short of breathtaking. And in late spring, it plays host to the now-famous Sculpture by the Sea exhibition.
20 Clovelly Bowling Club is another great option down this way, perfect for a few coldies. Or cool off with a snorkel at Clovelly Beach and get cosy with the famed blue groper that calls it home. Clovelly Bowling Club, Ocean St, Clovelly, (02) 9665 1507
21 For more chilled-out waterside pursuits, picnic at Nielsen Park - which we swear feels like Europe - and take a dip in Shark Bay (don't worry, the nets are up).
22 Further afield, at the southern end of the city, catch the 1930s ferry from Cronulla to Bundeena and explore this arty hamlet and Royal National Park - Australia's oldest.
23 At the other end of town, one of our all-time favourite Sydney experiences is catching the seaplane from Rose Bay to Berowra Waters Inn (set on the Hawkesbury River) for lunch. Did someone say jetset?
24 While Sydney's beaches get all the press, the city is also home to some hot swimming pools. North Sydney Olympic Pool offers incredible views of the Harbour Bridge and a nice café, while the Andrew (Boy) Charlton Pool is the most glam public pool we've seen, and a big hit with visiting celebs. North Sydney Olympic Pool, Milsons Point, (02) 9955 2309; Andrew (Boy) Charlton Pool, Mrs Macquaries Rd, The Domain, (02) 9358 6686
25 Where to stay? The Establishment Hotel is hip, ultra-urban and all-round fabulous. Make like a rock star and base yourself at this perfectly located boutique accommodation. 5 Bridge La, Sydney, (02) 9240 3100
26 Once you've unpacked, head a few blocks down George Street to The Strand Arcade, which is not only architecturally beautiful but home to some of Australia's favourite names: Dinosaur Designs, Funkis, Kikki K, The Corner Shop and Lisa Ho among them. Finish it off with the penne alla puttanesca and a glass of nebbiolo upstairs in the Pendolino café. The Strand Arcade, 412-414 George St; Pendolino, Shop 100, Level 2, The Strand Arcade, (02) 9231 6117
27 Still in retail therapy, seek out some of Sydney's best street looks at Via Alley, on Crown Street and in The Galeries Victoria, and Incu, in Paddington and The Galeries Victoria. Via Alley, Shop RG26a, The Galeries Victoria, 500 George St, and 285a Crown St, Surry Hills, (02) 8354 0077; Incu, 256 Oxford St, Paddington, and Shop RG23-24, The Galeries Victoria, 500 George St, (02) 9331 6070
28 For a cluster of Australia's best designers, including Scanlan & Theodore, Willow, Ksubi, Kirrily Johnston and Camilla and Marc, head to the corner of Glenmore Road and Oxford Street in Paddington. Other hot new kids on the block in these parts include Kate Sylvester (on Oxford Street) and Josh Goot (in Glenmore Road) While you're in the 'hood, also check out ACNE and Land's End before refuelling with the pumpkin and Woodside goat's cheese salad with bacon, croûtons and red wine vinaigrette at Jackies Cafe. Yum. Jackies Cafe, 1c Glenmore Rd, Paddington, (02) 9380 9818
29 Moving from fashion to homewares but still in Paddo, you'll love quirky interior stylist Sibella Court's installation-like shop, The Society Inc. She changes her store's theme every three months. Kooky. 18 Stewart St, Paddington, (02) 9331 1592
30 For high-end, homegrown skincare, also sold in Colette Paris and Barneys New York, head to Aesop. 72a Oxford St, Paddington, (02) 9358 3382
31 Over at posh Potts Point, the cool kids begin with breakfast at Fratelli Paradiso and then wander up to Becker Minty Women for frocks that rock. Down the hill in Elizabeth Bay, Bloodorange cherry-picks pieces from a cool range of hip labels such as Lover and APC. Fratelli Paradiso, 16 Challis Ave, Potts Point, (02) 9357 1744; Becker Minty, cnr Macleay St & Greenknowe Ave, Potts Point, (02) 8356 9908; Bloodorange, 35 Elizabeth Bay Rd, Elizabeth Bay, (02) 9357 2424
32 More of a market shopper? You'll like Sunday's Bondi Markets and might even spot a future fashion star selling his or her wares (lots of designers kick-started their careers here). Or try Saturday's Balmain Market, where there are plenty of vintage options to fossick through.
33 If it's getting towards beer o'clock, favourite watering holes include the wonderfully decrepit Hero of Waterloo. Sitting away from the worst of the tourist crowd on the inner-harbour side of The Rocks, it's a bona fide great old pub, and if you time your visit right on the weekend you might just catch an afternoon performance from what must be Sydney's oldest jazz band. See also the Lord Nelson for history with a micro-brew edge. Hero of Waterloo, 81 Lower Fort St, Millers Point, (02) 9252 4553; Lord Nelson, 19 Kent St, Millers Point, (02) 9251 4044
34 There's no better way to get elegantly wasted than a crawl around the city's wine bars. De Vine, Vini, Bentley Restaurant & Bar and Aperitif should be top of your list, as should Wine Odyssey, Time to Vino and Ash St Cellar. For in-your-face glam, cocktails and cabanas, head to Ivy Pool Club, on the top deck of hotelier Justin Hemmes' multimillion-dollar shrine to food, drink and la dolce vita. Pack a bikini and some attitude. De Vine, 30 Market St, Sydney, (02) 9262 6906; Vini, 3/118 Devonshire St, enter via Holt St, Surry Hills, (02) 9698 5131; Bentley Restaurant & Bar, cnr Crown & Campbell sts, Surry Hills, (02) 9332 2344; Aperitif, 7 Kellett St, Potts Point, (02) 9357 4729; Wine Odyssey, cnr Argyle & Harrington sts, The Rocks, 1300 136 498; Time to Vino, 66 Stanley St, Darlinghurst, (02) 9380 4252; Ash St Cellar, 1 Ash St, Sydney, and Ivy Pool Club, 320 George St, both (02) 9240 3000
35 Sure, the bar-bars are good, but restaurant-bars the likes of Lotus and Longrain come with guaranteed superior snacking, while the burger in the drinkatorium at Rockpool Bar & Grill is almost an event in itself. Lotus, 22 Challis Ave, Potts Point, (02) 9326 9000; Longrain, 85 Commonwealth St, Surry Hills, (02) 9280 2888; Rockpool Bar & Grill, 66 Hunter St, (02) 8078 1900
36 Of the restaurant bars, none sums up the Sydney experience as well as Icebergs Dining Room & Bar, nestled on the southern clifftop - the views of Bondi are picture-book. Stop in at sunset for a Campari soda apéritivo (the toasted spelt, crab, rocket and aioli sandwich is pretty fine too) or perhaps dessert and a digestif after dinner at that other local favourite, North Bondi Italian Food (we like to walk along the beach from one to the other). Icebergs Dining Room & Bar, 1 Notts Ave, Bondi Beach, (02) 9365 9000; North Bondi Italian Food, 118-120 Ramsgate Ave, North Bondi, (02) 9300 4400
37 And the best pizza in town? Suburban Haberfield was once the pizza heartland, but today's challengers include Balmain's Rosso Pomodoro, Darlinghurst's Lucio Pizzeria and the just-off-the-strip Pompei's at Bondi Beach. Rosso Pomodoro, Shop 90-91, 24 Buchanan St, Balmain, (02) 9555 5924; Lucio Pizzeria, 248 Palmer St, Darlinghurst, (02) 9332 3766; Pompei's, 126-130 Roscoe St, Bondi Beach, (02) 9365 1233
38 For great value, breakfast at Café Sopra, above the superb Fratelli Fresh provedore, is hard to beat, with peerless Vittoria coffee and chef Andy Bunn's roast pork and caramelised witlof panino, and frittata with goat's curd and baby basil. 7 Danks St, Waterloo, (02) 9699 3174
39 Sydney's culinary melting pot can be further enjoyed if you hop on the train to Cabramatta for the afternoon - go enjoy a slice of Ho Chi Minh City without leaving the state.
40 Speaking of things Vietnamese, An Restaurant does hands-down the best Vietnamese beef noodle soup outside, well, Vietnam. 27 Greenfield Pde, Bankstown, (02) 9796 7826
41 And, while we're over this side of town, Jasmin in Lakemba does falafels that will redefine your idea of falafelness. 30b Haldon St, (02) 9740 3589
42 Lunch at the original Spice I Am introduces you to the most authentic Thai in Australia, and at these prices offers perhaps the best bang for your buck of any Sydney restaurant. More Sydney-stylish than Spice I Am's Bangkok-grunge, Sailors Thai Canteen is the best inexpensive(ish) eating in The Rocks - the perfect place to refuel post-gallery or pre-theatre. Spice I Am, Shop 1, 90 Wentworth Ave, Surry Hills, (02) 9280 0928; Sailors Thai Canteen, 106 George St, The Rocks, (02) 9251 2466
43 Late-night congee at the Golden Century, open till 4am, is a must, as half of Sydney's top chefs can attest, but for something a little more fiery, try supper at the nearby Chat Thai, until 2am. Golden Century, 393-399 Sussex St, Haymarket, (02) 9212 3901; Chat Thai, 20 Campbell St, Haymarket, (02) 9211 1808
44 Sydney does seafood better than almost any other city. Get a taste with 12 kinds of oysters from around the country shucked to order at The Boathouse on Blackwattle Bay. Or make a beeline for Fishface, where you can get seafood of equal quality but in a much more casual environment. The fish and chips are killer. The Boathouse on Blackwattle Bay, end of Ferry Rd, Glebe, (02) 9518 9011; Fishface, 132 Darlinghurst Rd, Darlinghurst, (02) 9332 4803
45Sydney Fish Market, the largest establishment of its kind in the southern hemisphere, is something of a foodie landmark. If you can't face the dawn wake-up for a tour of the auction floor, then a class at Sydney Seafood School, on the first floor, is a must, especially now that it has been freshly renovated to a stunning sheen by designer Michael McCann. Bank St, Pyrmont, (02) 9004 1100
46 If you prefer to discover the region's best produce in its pre-cooked form, keep an eye out for the local growers' markets at Northside, Pyrmont, Eveleigh and the Entertainment Quarter. (And if you see a Pat and Stick's ice-cream sandwich stall, buy as many as you can carry).
47 Carnivorous tastes will be met and then some at Victor Churchill. Less butchery than meat boutique, it's the Tiffany of the tenderloin. 132 Queen St, Woollahra, (02) 9328 0402
48 New-wave pastry: whether your taste for pastry leans more to MasterChef or Pierre Hermé, Sydney's latest generation of pâtissiers has something for you. Check out TV favourite and bona fide kook Adriano Zumbo's Balmain mothership for desserts with names as wild as their flavours, or nip over to Black Star to see Chris Thé deploy skills earned at the city's finest diners in an attractively boho café shopfront. Adriano Zumbo, 296 Darling St, Balmain, (02) 9810 7318; Black Star, 277 Australia St, Newtown, (02) 9557 8656
49 Sydney might have a stranglehold on the very top end of the nation's restaurant market, but it still has plenty of edge and spark - qualities in no short supply at Bodega, a Surry Hills hot spot where Spanish tapas and South American flavours, tattoos, rockabilly hair and many decibels of eclectically chosen music come together in glorious technicolour. 216 Commonwealth St, Surry Hills, (02) 9212 7766
50 A perfect way to end a day in the city? Enjoy a postprandial browse through the shelves at Ariel bookshop, which boasts a beautiful selection ranging from classics to coffee-table tomes. 103 George St, The Rocks, (02) 9241 5622; 42 Oxford St, Paddington, (02) 9332 4581