C. James Dale and Carla Grossetti, for CNN • Updated 24th March 2017
Editor's Note — CNN Insider Guides are thoroughly checked for accuracy. Given the fluid nature of the travel industry, however, some listings may fall out of date before guides can be updated. The best practice is to confirm current information on official websites before making plans to visit any business or attraction.
(CNN) — Gorgeous. Vibrant. Sexy.
You burn through a lot of adjectives describing the best of Sydney, with its great beaches, top-notch restaurants and endless bars and nightclubs.
For a place that started out as a penal colony in the late 18th century (and for thousands of years before that, Aboriginal land), Sydney's come a long way, from opening its iconic Opera House in 1973 to hosting the Olympics in 2000.
These days, it's a regular on all of those "top 10 places to live in the world" and "most expensive cities in the world" lists.
An overheated real estate market means homes that sold for $160,000 in the late 1970s now go for more than $4 million. (That's one example, but you get the idea.)
The creep of gentrification is claiming street after street, turning once-dodgy neighborhoods into havens for the trendy set worthy of that "best of Sydney" tag.
Living in a city that's popular, cool and costly is a fact of life for Sydney's 4.6 million residents, an outdoorsy and environmentally friendly lot. They'll charm you with a "G'day," "No worries" or "How ya goin'?"
You'll contemplate moving here so you too can enjoy being in paradise full time -- or at least talk like you do.
Failing that, you'll consider extending your vacation or start planning a return voyage even before you hit the airport
Nice view -- it cost Shangri-La $20 million to perfect.
Every room at the Shangri-La has a best of Sydney view of the harbor, although some rooms (and views) are better than others.
Hotel operators spent $20 million in 2011 to refurbish 477 guestrooms and suites.
A modern Asian style focused on the Oriental blossom ties things together.
A nice touch, but nothing tops sitting in your room and staring at the Opera House and Harbour Bridge.
Blu Bar on the 36th floor has some of the best cocktails in Sydney, all of which come with quite the view.
The Four Seasons Sydney has a great location in The Rocks, a vast lobby, rooms with "Yup, I'm in Sydney" vistas and the largest heated outdoor hotel pool in the city.
And unbeatable beds and bedding.
Designers gave the hotel a makeover before the 2000 Olympics (it was the base for the IOC during the Summer Games).
Then in 2009, they updated the 531 rooms.
Some features still feel dated -- doors, fixtures, wonky elevator buttons -- but the views of the Opera House and harbor don't disappoint.
The pool is a good place to lounge before or after schlepping around Sydney.
Viewed from the harbor, the Marriott looks like a squat younger sibling getting muscled out by its bigger, five-star rivals and the skyscrapers that populate The Rocks and Circular Quay.
But it's still among the best of Sydney hotels.
Owners spent millions renovating the rooms in 2011, giving them a more modern feel (although the beds at the Shangri-la and Four Seasons are still better).
Staff are helpful and genuinely eager to debrief you on your day or assist you in planning your itinerary for the next one.
The Marriott is also a little closer to the Royal Botanic Gardens.
Another bonus: the hotel has an Avis car rental outlet at the entrance.
With its loft-like designed spaces and dimly lit hallways that smell of incense, this place feels like your chic pied-à-terre in Sydney.
The majority of the 31 rooms (save two penthouses) have queen beds, sleek bathrooms (some with sliding walls), Bose sound systems, AppleTVs and iPads loaded with music, information on in-room dining and things to do in the city.
No harbor views here, but you won't need those when you're hanging at the cavernous Establishment Bar or the Ottoman-inspired Hemmesphere.
Breakfast at Gin Garden (brick walls, soaring glass ceiling) are great, the pancakes in particular.
Hughenden Boutique Hotel
This grand old dame has a colorful back story: while it started out as a family residence in the 1870s, its incarnations include serving as a nurses' home, dance hall and college for young ladies.
Now the rejuvenated hotel -- which is surrounded by designer boutiques -- is elegant and airy.
Vincent is a new French-style brasserie downstairs.
The cozy rooms are compact, but they're also comfortable and affordable.
Terrace suites are roomier.
The property is filled with turn-of-the-century furnishings, award-winning art and covetable collectibles.
For anyone wanting to be in the thick of Sydney's bar, restaurant and nightlife quarter, hotels don't come much better situated than this.
Some suites are on the small side, but there are great add-ons, such as free gym passes, iPod docks in rooms and cheap Internet connections.
Chic accommodations range from standard rooms to two-bedroom apartments.
Sydney Harbour YHA
This award-winning hostel has best of Sydney views of the harbor and access to Australia's largest archaeological site, the Big Dig.
The builders spent $1 million on environmental initiatives, including air conditioning that shuts off when guests leave their rooms.
Accommodations range from six-bed mixed rooms to twins and doubles.
Sepia's meteoric rise has stunned even jaded Sydney foodies.
Sepia made it to the top of Sydney's restaurant scene in three short years thanks to the culinary and management skills of business/life partners, chef Martin Benn and Vicki Wild.
The Sydney Morning Herald called this eatery's rise "nothing short of meteoric," and has awarded Sepia its top award (three chef hats) in its annual "Good Food Guide" three years in a row.
Most nights are booked solid, with a waiting list of 300 for Benn's tasting menu on Saturday evenings (now expanded to lunch).
Wild and Benn worked at Sydney's top Japanese restaurant, Tetsuya's, for a number of years, so their interest in Japanese cuisine is woven through the menu.
Scallops coated with nori. Dollops of avocado cream posing as wasabi.
You'll even find seaweed in one of the desserts.
Diners dismantle Benn's elaborately prepared dishes with care.
One offering -- Murray cod with its puffed skin and whipped-up foam of yuzu -- appears to be leaping out of the sea.
The signature dessert is a candied strawberry with frozen sorbet inside, which can be opened with the tap of a spoon.
Chef Neil Perry has taken things up a notch with the relocation of Rockpool to the oh-so-swanky Heritage-listed Burns Philip building.
The Sydney CBD dining room is alive with the perfume of star anise and slow-braised beef cheeks -- gutsy head chef Phil Wood is jump-starting things at the high end of town.
Like Perry, Wood is an authority on Asian flavors that he bolsters with great ingredients.
This is a wonderful new space with soaring ceilings, low-slung leather chairs and staff who can't do enough for you.
A good bet is the spicy white-cut chicken salad with fried bamboo and XO chili sauce; or bo ssam shoulder and miso-braised beans. In three words: worth the splurge.
What is it with the views here? Quay has a stunning terrace.
Executive chef Peter Gilmore's talent for dreaming up culinary creations landed Quay a spot on S.Pellegrino's World's 50 Best Restaurants of 2012 -- clearly one of the best of Sydney restaurants.
As the name suggests, Quay is located by the water, with floor-to-ceiling windows providing views of the Opera House and Harbour Bridge and interior mirrors reflecting it all back to diners, who flock here year-round and jockey for a spot on New Year's Eve.
Staff in simple black outfits deliver dishes that have their own creative touches, such as mud-crab congee or rhubarb-endive-beetroot salad on a bed of granules made from pomegranate-and-molasses-soaked bread. Really.
A team of sommeliers helps patrons navigate the extensive wine list.
The eight-texture chocolate cake and Gilmore's signature snow-egg dessert became sensations after being featured on "MasterChef Australia."
The menu for this hole-in-the-wall eatery is written on big blackboards and it changes daily.
Eaters share side dishes of grilled broccoli or farinata (pancake made of chickpea flour) and linger over plates of gnocchi and prawns or culingionis (Sardinian ravioli) of braised lamb with potato, olive and thyme.
Vini, which has a sister restaurant called Berta, serves a four-course set menu on Tuesday nights, highlighting a region in Italy.
North Bondi Fish
Australian chef Matt Moran and business partner Peter Sullivan have planted their flag in the sand at this iconic Sydney beach with North Bondi Fish, the more wallet-friendly surf-loving cousin of Aria and Chiswick.
The Bondi hip parade includes off-duty lifeguards, grizzled surfers and beautifully boho models who look like they've stumbled off the set of Bondi Rescue.
Style-wise, it's beach clubby.
As the name suggests, it's all about the seafood: the menu encourages groups to join together on plates of oysters and prawns flecked with lime and oregano, and grilled whole fish of the day with orange and fennel.
Four In Hand
With its warm and intimate atmosphere, this gastropub is a favorite with locals and foodies, ranked by some patrons as, "the best place to eat in Sydney."
Four in Hand dishes are heavy on the meat, but meat that's been lovingly prepared: 12-hour braised lamb shoulder with baby carrots and Irish-style mashed potatoes, roast beef rump with sweet corn and whole suckling pig with accompaniments (requires 48 hours' notice and a minimum of 10 diners).
Head chef Colin Fassnidge, who has won endless praise since taking over in 2005, subscribes to the nose-to-tail philosophy -- cow's tongue or pig's tail could end up on your plate.
A funky and fun place to eat, this sprawling warren has great food, quirky cocktails and a courtyard crawling with its usual hipster quota.
The atmosphere is lively, with people at tables for twos or fours, or long communal tables, chatting over the East-meets-West food.
The semi-industrial decor includes exposed wood and ropes.
The Harbour Bridge can be seen in the distance through a big picture window.
Highlights include corn on the cob basted with chili-infused sour cream and smothered in Parmesan cheese, beef and pork sliders and the Buddha vegetarian salad.
Ms. G's takes reservations only for lunch on Fridays and Sundays, or for large groups.
The bar is partially wallpapered in black-and-white photocopies of old Rolling Stone, Hustler and Playboy covers.
Diners eat Vietnamese and Latin American dishes under the watchful gaze of Queen Elizabeth II.
Dishes worth a try include the Pho-Evermore Nourished Soup, Pretty Dumplings and Three Sisters (rice paper rolls stuffed with veggies and grains).
A selection of non-dairy and wheat-free "cheesecakes" is on the dessert list.
Bring your own wine -- corkage is $3. Reservations recommended.
The nightclub sensation that has wowed crowds in New York and Las Vegas arrived this year in Sydney.
Paris Hilton was at the opening. (Does that still matter? I guess if we have to ask ... )
The club is more Vegas than Manhattan, owing to its location inside a casino.
You'll either love the crowd or hate it.
Girls in skimpy skirts and tops.
Guys in dressy attire or tight T-shirts. All lip-synching their way (flubs and all) through classic club songs and mixes that blend Toto with Kanye.
It's not easy to find the Baxter Inn, and that's how the regulars like it at this best of Sydney clubs.
On Clarence Street, look for the sign that says "Sprinkler room for 156 Clarence Street."
Take the walkway to an alley to find the doorman and the black velvet rope. Then go down a set of concrete stairs to a basement bar.
Exposed wooden beams and metal supports, low lighting and blaring blues music help set the mood, along with boxing and horse-racing posters.
The mixed-age crowd is decked out in suits and skirts or T-shirts and jeans.
The drinks list includes cocktails and a fair number of wines.
More than 450 whiskeys sit on an eight-tiered shelf behind the bar, ranging in price from $7.50 to $115 for a shot.
There's no door list, no bookings and no functions.
"It's just a good spot to hang out, to have great drinks and great service," says one staffer.
Midnight in Paris. Madagascar Manhattan. This Little Piggy Drank Whisky.
Just a few of the colorfully named drinks at Hinky Dinks, which aims to inject a bit of 1950s fun into Sydney's serious cocktail scene.
Tiled floors, a swanky lounge area and red leather stools (with piano benches thrown in for no good reason other than they're comfortable) all attempt to transport patrons to a bygone era.
The bar menu is filled with tasty options, such as beer-battered onion rings, Spanish meatballs and pan-fried olive and Parmesan sandwiches.
BYO or order wine from the board at 121BC.
People who love Italian wine in an intimate setting have been making their way to this tiny best of Sydney spot for more than a year.
The ever-changing wine list (on a blackboard) covers each of Italy's 20 grape-growing regions.
Glasses range from $6 to $15.
Patrons can buy a bottle from the cantina, which stocks more than 300 biodynamic wines from all over Italy, and pay a $15 corkage fee.
The bar, which has ties to Italian restos Vini (just around the corner) and Berta, offers a simple menu of dishes that can include olive and focaccia, balsamic pork ribs and ricotta with ox-heart tomatoes and fried capers.
Prices range from $6-16.
If only the brooding brick walls of this rustic warehouse could talk.
The venue has led a bawdy old existence both as a gaming hall for Navy ex-serviceman and as a Chinese brothel.
Now, the striking space has been rejigged to become the permanent abode for Nomad, the city's very own cellar door.
The warehouse, which hangs onto the skirts of Sydney's Surry Hills, is anchored by artwork and hardwood pillars.
Those in the mood to sprawl may try the smoked pork empanadas with harissa or the oysters with a cava vinegar dressing, dishes that best represent the cooking, which is rooted in the past.
Cure, smoke, ferment, pickle, repeat.
The Shakey is a straightforward, take-me-as-I-am pub that's been keeping patrons fed and lubricated since 1879.
Schooners of Tooheys New, Bulmers Original Cider and Cascade Premium Light go for around $5 (cash only).
Glasses of wine are in the same price range.
If the sight of the stained and trampled carpet hasn't put you off food, there's a range of picks -- none of the main meals is more than $12.50.
Cheap options and atmosphere make Shakeys a favorite with beefy local guys and quirky 20-somethings.
The tour of one of the world's most iconic buildings is a clever mix of access, video and facts.
Best of Sydney? Most definitely.
Good humored guides give insight into the origins, construction, controversy and conflict leading up to the opening of the Sydney Opera House in 1973.
It ended up more than a decade late and nearly $100 million over budget -- a national lottery helped pay it off in 18 months.
Since then, 110 million concertgoers and tourists have visited this place, which is home to the Sydney Symphony Orchestra, Opera Australia and The Australian Ballet, all of whom you can watch rehearse, depending on the timing.
Sydney Opera House has also hosted pop musicians (Janet Jackson, Sting), sumo matches, boxing bouts and bodybuilding competitions.
You'll find out about that, and why a chicken fell on a cellist's head in the 1970s, if you go on the tour.
Oh, and why its creator, the late architect Jørn Utzon, never traveled to Sydney to see his masterpiece.
An Australian icon closely studies a lesser-spotted tourist.
The Taronga Zoo, which sits on a sloping hillside above the harbor, is another Sydney landmark.
Nearly a century after its opening, zookeepers are focusing more on conservation than display.
Along with showing off elephants and gorillas, platypus and potoroos, they're actively helping save species that include a couple of endangered frogs you've never heard of.
Look up the Corroboree and Booroolong if you're curious, and the Tasmanian Devil, which is predicted to become extinct in the wild within 15 years if conservation efforts don't make a difference.
The zoo's "Roar and Snore" program allows you to camp overnight in safari tents and wake up to the sound of lions.
One of the best of Sydney attractions, for sure.
Here's your chance to be part of the crew on an America's Cup yacht.
The Sailing Sydney team takes groups on three-hour trips into Sydney Harbour, getting participants to haul up sails or keep the boat on course.
You can also just sit and enjoy the scenery: sailing under the Harbour Bridge and waving to the people climbing it, breezing past the Opera House and surveying the city's dynamic shoreline.
Crew members have a lot to say about sailing.
They're also quick to point out the sights along the way and explain their significance.
Sydney Sailing, Suite 110 Jones Bay Wharf, Pirrama Road, Pyrmont; +61 (0) 2 9660 9133; America's Cup Experience, $129 for adults, $99 for children (10-17 years); America's Cup Racing Experience, $169 for adults, $139 for children (10-17 years)
Hop a ferry
Dozens of ferries sail every day from the main hub, Circular Quay.
One of the best ways to get around is to buy a Sydney Ferries MyMulti day pass ($22 for adults; $11 for children) or a week ($61 for adults; $30.50 for children).
It grants unlimited rides on government ferries, buses, light rail and trains (some zone restrictions apply).
You can hop a ferry (and connecting bus) to visit the pristine and picturesque Balmoral, where you can enjoy the relaxed atmosphere as you walk along the beach.
The seaside municipality of Manly has alluring beaches, surfing, boutiques and myriad coffee shops (Bean Rush Cafe, Barefoot Coffee Traders, more).
A popular Watson's Bay meal is fish-and-chips at Doyles on the Beach.
My Sydney Detour
It's kind of cool to walk out of your hotel in the morning and see the mustachioed Richard Graham leaning against his port-sea blue 1964 Holden EH premier, ready to chauffeur you around to experience the best of Sydney.
The 29-year-old designs intimate tours aimed at making visitors feel like locals.
His car -- with its original fixtures, two-tone horn and absence of power steering -- is a throwback to the days when Australians first got into motor culture, and it elicits stares, smiles and compliments.
"You're a local in this car," he'll tell you as he takes you through off-the-beaten-track neighborhoods such as Redfern, Darlington and Newtown, stopping at tiny cafés for cappuccinos and chatting to you about Australian history, aboriginal issues and Sydney's gentrification.
Graham's tour takes you along the city's gorgeous coast and makes stops at lookouts, cemeteries and exclusive neighborhoods.
He loves Bronte Beach, thinks Bondi Beach lacks soul and is obsessed with Captain Cook.
Richard is quirky and makes for good company, taking you to places you wouldn't otherwise see or with a tour group.
His detours can be customized.
Visitors who want to explore Sydney at street level can join Graham's wife, Berangere, who offers walking itineraries that are far from pedestrian.
The former French actress uses a mix of drama, storytelling and humor to deliver her informative take on the colorful city.
Walks range from dawdling detours, where spectacular sightseeing is the thing, to all-day perambulations on which ramblers hike to out-of-the-way parts of the city.
Shoppers will want to make a walk along Oxford Street in Paddington a priority, as there's a wealth of boutiques between Victoria Street and Jersey Road.
Fleur Wood is an Australian designer who creates vintage-meets-modern-day-girl clothes for women.
Her eponymous store also has quirky accessories, such as the must-read picture book, "All My Friends Are Dead."
Come As You Are sells skinny jeans, silky designer pants and wispy cotton shirts by international labels such as Sweden's Odd Molly, along with J Brand and Haute Hippie of the United States.
The Other Side stocks a mixed bag of brands, but focuses on the Australian line Three Over One, with its blue-and-white striped tops, green twill trousers and sweats (traditionally for men, now expanding to women).
In Paddington, a detour down William Street is worthwhile. Start off on the corner at T2, an outlet of the popular Australian boutique tea chain.
There are any number of cute stores (Just William Chocolates, Elegantly Scant fine lingerie and I Like Birds new and vintage homeware, to name a few) and you can get a panini, pasta and coffee at Paddington Alimentari.
Paddington Markets is an institution -- a cornucopia of stalls sell everything from organic cotton tees to pop art imagery to the latest fashion.
As well as being a fantastic platform for creative types to show off their art, it provides an opportunity to gawp at an idiosyncratic crowd.
Malls in the CBD
Yes, Sydney does normal stuff, too.
A couple of malls stand shoulder-to-shoulder in Sydney's Central Business District, offering some of the best of Sydney shopping options to keep credit cards humming.
The Queen Victoria Building, a 19th-century sandstone structure that fills a city block, was originally designed to be a fresh produce market.
It's now home to a diverse array of stores, from Adidas to Lush to Ralph Lauren, along with a few charming coffee shops.
Westfield Sydney is the QVB's modern younger sister -- a slick, six-level structure with stores to suit all tastes.
Shoppers can find alternative and accessible brands (Zara and Esprit) on the bottom level.
Top designers such as Hugo Boss and Diane Von Furstenberg occupy level three.
Level four is where you'll find Australian designers -- Saba, Sambag, Little Joe and others.
There's a gourmet food court on level five.
The Rocks Markets
Local vendors and artisans trot their stuff out on the weekends (food stalls open Friday) at this outdoor market, open year round and among the best of Sydney browsing spots.
There's lots of stuff to sift through -- bags, scarves, jewelry, artwork, handmade soap and boomerangs spring to mind.
You can pick up "Roo Balls" for that special someone who needs kangaroo testicles (hair-covered scrotum included) attached to a bottle opener ($30 or $100 for four).
It's a great place to get souvenirs.
Wine Odyssey Australia
This is one-stop shopping for anyone with an interest in fine Australian wine, encompassing a wine shop, wine bar, tasting rooms (Wine Journey Room and the Tasting Theatre) and a restaurant.
Wine Odyssey buys exclusively from independent and family-run wineries.
No "Big Mac" wines, they'll inform you, such as Wolf Blass and Jacob's Creek.
Instead, you'll come across names like The Standish, Savaterre and Cockfighter's Ghost.
Critically acclaimed bottles include Tyrrell's Hunter Semillon and the Bannockburn 1996 Pinot Noir, plus a solid selection of Barossa Valley Shiraz.
Wine Odyssey has limited editions by small vintners, who make fewer than 1,500 bottles and adorn them with handmade labels.
Bottles run from $15 to $1,500.