My pick is the groovy Kirketon Hotel, a member of Australia's boutique Eight Hotels collection. Located on a leafy portion of Darlinghurst Road, it's just steps away from bustling Victoria Street. After a full remodel in '08, the 40-room Kirketon is now a swank goth/art deco/mod-hybrid. I love it, mirrored hallways, dim lighting, chandeliers, smokey color scheme, black facade, and all. It's slick, sexy without trying too hard, and the bright, well-designed rooms are kitted out with comfy beds and modern amenities.

Despite the trendy vibe, the Kirketon is peaceful and not at all pretentious, thanks in part to the genuinely friendly, helpful staff. Come night, however, this hotel is hopping because of its award-winning bar, Eau de Vie (more on that, below).

Eating
Darlinghurst has lots of dining options, but for me, it's all about breakfast. Right across from the Kirketon is La Petit Creme, a funky French coffee house serving delicious crepes, pain chocolat and other breakfast treats, and bowls of cafe au lait.

Arguably one of Sydney's most beloved breakfast spots (equally wonderful for lunch) is Bill's, owned by acclaimed chef Bill Granger. Granger is one of a handful of Aussie chefs who helped put "Mod Oz" cuisine on the map. Expect bright, seasonal fare inflected with Mediterranean and Asian flavors. It's a total travel article cliche, but the ricotta hotcakes with bananas and honeycomb butter, sweet corn fritters, or toasted grain cereal with vanilla-poached fruit, yogurt, and honey really are the best way to start a day of sight-seeing.

My new breakfast (lunch/snack/drunken late-night munchies) obsession, however, is Infinity Sourdough Bakery, located around the corner from the Kirketon. I'm totally convinced that anything that emerges from the ovens at this adorable takeaway will be amazing. Four visits in a single day did nothing to disprove this theory (not counting other carbo-loading sessions). The almond croissants are life-changing, but the pizzettas, ham and cheese turnovers, bread, and other pastries are also excellent.

...and Drinking
Wherever you lay your head, be sure to stop by Eau de Vie, 2010's Australian Bar Awards Bar of the Year. It's a living room-like spot on the Kirketon's ground floor, with a moody, Prohibition-era vibe (I'm of the "it can't be a speakeasy if it legally sells cocktails" school of thought, because I'm a pain in the ass like that.)

Eau de Vie specializes in seasonally-changing, contemporized classic cocktails that, if a bit precious and theatrical, are crafted with the utmost precision. If you're interested, one of the friendly mixologists--all of whom possess encyclopedic knowledge--will tell you everything you might care to know about your drink. Said drinks don't come cheap, although there are plenty in the $16USD range. The $32USD syrupy smooth Old Fashioned made for me by "Dr. Phil," however, was without a doubt the best I will have in this lifetime. Why so spendy? Ron Zacapa Centenario 23 (as in years-old) rum, housemade bitters, a puck of ice compressed to order in a copper Tyson ice mold, and open flame were involved.

In the small bar category, Darlinghurst boasts some of Sydney's favorite newbies (all of the following serve bar snacky food/small plates). At The Passage, expect refreshing libations such as the Professor Plum (plums macerated in Queirolo plum pisco, shaken with lemon juice and Madagascan vanilla syrup), or a Coconut and Kaffir Lime Daquiri, served up with a garnish of pandan leaf.

Lotforty, a miniscule candlelit tapas bar, offers up jugs of sangria ($20AUD), as well as cocktails, and fried, grilled, and crispy treats such as "bbq" King Prawns with orange, fennel, and mint salad. At wine bar Love, Tilly Devine (named after an infamous neighborhood Madame of the 1930's), the extensive list of international offerings is meticulously chosen and categorized. Sip with slow-roasted octopus with new potatoes and aioli, Macleay River rock oysters, or Burrawong duck liver pate with sweet and sour onions.

Technically, Sticky Bar is in Surry Hills (known for its eclectic shops and ethnic restaurants), just a short walk from the heart of Darlinghurst. Sticky is such a funky, sexy, odd little space I can't help but include it. It's a bitch to find (especially after a few drinks), as you need to enter through sister restaurant Table for 20, and climb a narrow flight of stairs to enter the bar. The decor is decrepit-Victorian-mansion-meets-Old-Hollywood: overstuffed vintage velvet chairs, leather ottomans, ornate chandeliers, exposed brick, and shadowy nooks and crannies. Order a glass of domestic wine or a wickedly strong cocktail from the blackboard menu, settle back, and watch the scene (the music's loud).

Shopping
Darlinghurst isn't the best place if you're a bargain hunter (try the vintage clothing stores in uni-district Glebe, instead). But if you have the cash (or are a bit of a masochist), you'll find no shortage of on-trend boutiques featuring up-and-coming Aussie clothing designers, shoes, high-end vintage, luxe skincare products, book stores and whimsical home decor. Darlinghurst Road, Victoria Street, and Liverpool Street also have a fair number of shops. I like Blue Spinach, a "luxury consignment" store where you can score affordable treasures if you do some digging. Popular boutiques include Diederic the Cat, which offers American and Euro fashions, and Alfie's friend Rolfe. This self-described "little Aladdin's Cave of Australian designer labels" is heaven if you're looking for quality sartorial souvenirs.

Getting There
Qantas flies non-stop to Sydney out of LAX and DFW, with extensive code share connections available from major cities throughout the country through the partnership with American Airlines. Tourism Australia's website will provide you with all the information you need to plan a holiday.

Click here to watch one of Eau de Vie's mixologists create a signature cocktail (don't miss Dr. Phil's "Whisky Blazer!")

[Photo credits: cottage and Oxford St., Flickr user iambents]