It may be winter in Sydney, but you wouldn't know it. Firstly it was warm and sunny (around 70 degrees each day) and the city was a buzz with locals and visitors soaking up the atmosphere and fine food. It had been a few years since I had visited the harbor city and while "everything old was new again" there were several very cool locales that had recently opened their doors so I felt the need to check them out, plus revisit a few of my favorite old haunts.

I was lucky enough to have my very own Sydney culinary and social scene mentor in the form of Henry Roth, the Australian incarnation of Tim Gunn (the mentor on Australian version of Project Runway). I figured that this style guru would never lead me astray and the result was a menagerie of Sydney hot spots where the well-heeled and those in the know come to dine and drink, but more importantly to see and be seen. Henry was quick to point out that the Olympic Games legacy for Sydney was "lots of tunnels and exorbitant prices," but even so, you can still eat well without completely breaking the budget. Keep in mind that what we call "entrees" in the U.S. are called main courses in Australia as entrees there (as they are elsewhere around the world) are actually the first course or appetizer.

Where to Eat & Drink

Bondi Icebergs Club (, not to be confused with the ritzy Icebergs Dining Room and Bar located above it (that boasts main courses for around A$45 and A$18 desserts), is a private membership social and swimming club (it is actually named after the crazy swimmers who dive into its ocean water pool throughout the winter, no matter what the temperature) located on a small cliff right at the southern tip of Bondi Beach. To gain admission, you only need to prove that you are a visitor and live more than three miles away by showing your photo ID. You then receive temporary club membership for only A$3. For that low price, plus the cost of a few drinks and bar snacks or a meal at the bistro, you get access to some of Sydney's finest views without the price tag. You can dive into a burger for around A$12, eat a huge bowl of muesli with fruit for under A$7 or savor an antipasto plate for a little over A$9. There's also a kids' menu and live music on weekends.

Jackie's (tel. +61/2-9380-9818) was a Bondi Beach landmark throughout the 1990s -- the place where you were just as likely to see media moguls and the richest man in Australia as rock stars and surfers -- all at the same time. It seems that Jackie's grew up and moved slightly inland and its new home is on Glenmore Road in fashionable Paddington, right off Oxford Street. Housed in a historic colonial building with exposed stonework and a small but inviting outdoor area, it is still the "it" spot for breakfast, a coffee or lunch during a heavy day of shopping at Oxford Street's hundreds of boutiques. Breakfast will only set you back around A$20-A$25, depending on your appetite, and the people-watching is free.

If you are looking for that quintessential Sydney Harbor experience, a drink at the Opera Bar (tel. +61/2-9247-1666; on the Lower Concourse level at Sydney Opera House is it, especially at dusk. The views are unsurpassed and after you've downed that martini or a one of their 40 wines available by the glass, try their own, award winning beer Opera Bar Organic Pale Ale (known as OB Pale) for A$6 a glass. There's a solid Tapas menu and quick pre-Opera/Theatre dinner menus if you need to eat and run. The Opera Bar Tasting Plate (for two) includes tuna with wasabi on chicory; Persian feta pastia; goats curd cigar with pear chutney; tempura cod with aioli and lime; spicy meat balls with tomato sauce; pork rillettes and croutons; and baby capsicum with ratatouille and pesto for a touch under A$47.

It seems that Melbourne restaurateurs are very popular in Sydney. Case in point, Hugo's Manly (tel. +61/2-8116-8555; which is in the best possible waterfront position on the wharf next to the ferries at Manly Beach and North Bondi Italian (tel. +61/2-9300-4400;, located on the beach front on the northern end of the Bondi Beach crescent. Hugo's offers exceptional dining at quite reasonable prices with a wide selection of contemporary Australian dishes, predominantly seafood priced at an average of A$27 per main course and exotic pizzas from A$20. There is an inviting wine list featuring Italian, Australian and New Zealand vintages. Make a reservation for lunch as far in advance as possible, specifying inside or out -- strangely they don't accept dinner reservations. North Bondi Italian is a little pricier and offers an eclectic mix of Italian regional cuisine and an interesting menu of pasta, offal, cured meats (Salumi) and diverse cheeses. They charge a 10% surcharge on Sundays and public holidays and a full meal here will probably set you back close to A$75 per person plus wine.

The Ivy (tel. +61/2-9240-3000; located on George Street in the city center is the newest exclusive offering from the owners of the nearby Establishment. It is a massive complex of some nine eateries, 18 different bars, a ballroom, boutiques and even a 25-metre swimming pool. The Ivy includes The Patio, a gorgeous outdoor space centered around a huge Japanese Maple tree and a spiral staircase; Ivy Bar, the main bar with views over The Patio; Ivy Lounge, with its creative and pricey signature; Teppanyaki, traditional acrobatic style cook-in-front-of-you Japanese but a modern twist; The Den, an intimate bar space with cozy sofas and live music; Mad Cow, A New York-style grill with a Peter Doyle (of the famous Doyle's Seafood I Watson's Bay) designed menu; The Kitchen, with informal eats like burgers and salads; The Terrace, an open-air area with cabanas overlooking the lower floors; and Royal George, a traditional British alehouse with pub food. If you are after intimate, this isn't it (except perhaps for the Den) but the Ivy is certainly entertaining, crowded and full of big spenders. Prices vary in each individual venue from main courses around A$25 to A$50 and drinks from around A$10 to A$20. There is often a line (queue) to get in to various bars here, so be sure to dress glamorous and use your foreign accent to charm the velvet rope doormen.

In Kings Cross, which was once just the notorious red light district, everything is becoming gentrified, up-market and extremely stylish. Although its technical address is in the snootier Elizabeth Bay, the 1970s landmark Gazebo Hotel once known for guests like Mick Jagger and its wild parties, it is very much the heart and soul of Kings Cross. The hotel is now home to the Gazebo Wine Garden (tel. +61/2-9357-5333;, a chic, indoor-outdoor venue when the young (and those that wish they were young) congregate to admire each other's beauty. The place is full of models, television actors and wannabe's. It's great for people-watching, decent food and it features 50 wines by the glass and hundreds by the bottle. The menu is mixed with seafood, pasta and contemporary Australian dishes with mains running at approximately A$25. The music is loud so conversations may be limited while you dine.

For a late night rendezvous, try the Piano Room (tel. +61/2-9326-0633;, just up the street from the Gazebo. There is no cover charge here despite it being like a Vegas club lounge complete with scantily clad waitresses and a jazz singer and pianist. The d├ęcor is vintage 1980s Vegas tacky with gold statues, chandeliers, velvet sofas and very low lighting. There's a doorman at the terrace door policing how many people get on to the balcony to be able to smoke -- there's actually a line to get outside, rather than to get in. The place is crowded and the drinks are very pricey -- about A$15 for a beer (to put that in perspective, at the Kings Cross Hotel across the road you can down a local beer for around A$3), but there's a certain ambience to the place that makes it an ideal spot for that night cap to round out a Sydney night out.

Where to Stay

When looking for a hotel in Sydney, there are literally hundreds of options -- with the most attractive central locations being the Rocks, Darlinghurst, and Bondi Beach. Although there are several large five-star properties and international groups, the boutique hotels are in my opinion a better alternative and offer better value for money without forgoing style, facilities and atmosphere.

Altamont Hotel (tel. +61/2-9360-6000; is located in the hub of Sydney's restaurant, bar and club scene in Darlinghurst and offers loft and deluxe rooms with queen or king size beds and en-suite bathrooms, a lounge, bar and Tuscan style rooftop garden. The hotel encourages late check outs so you sleep in and relax on the day you leave. Prices here are great, with deluxe rooms priced at A$129 per night or only A$119 per night if you stay a week or more. Loft rooms are about A$8 more per night and they can also configure a family room to sleep up to A$6 for the same price as a regular deluxe room, an absolute bargain considering the position and quality of the hotel. All prices include tax.

Just down the road, you will find the Kirketon Hotel (tel. +61/2- 9332-2011; a recently refurbished boutique hotel with standard double rooms priced from A$155 per night including tax and premium rooms from A$175. Some of the city's best cafes and restaurants are located footsteps from the hotel and from here you can walk to Woolloomooloo, Kings Cross, Paddington, and Potts Point within minutes.

The same hotel group also runs the Pensione Hotel (tel. +61/2- 9265-8888; located in George Street for those who would prefer to be in the city/Rocks area. It is almost a combination of an up-market hostel and boutique hotel with chic minimalist rooms priced from A$99 per night including tax and a guest lounge complete with breakfast area, kitchenette, Wi-Fi, Internet kiosks and coin-operated laundry facilities