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AFAR chose a destination at random—by literally spinning a globe—and sent Chris Colin on a spontaneous journey to Iceland.

Woolloomooloo’s quirky name was sourced from a town in Australia, as are the coffee beans used to make its signature “flat white” coffee drink (served in a glass, Aussie style). Opened by a Taiwanese-Australian architect, this popular eatery offers a solid menu of Western dishes in an industrial-chic space. Though it’s called a “cafe”, Woolloomoolo is more communal canteen than intimate coffee shop, boasting long wooden butcher tables and steel-clad walls. Though its menu includes staples such as pizza and pasta that are found in almost all of the many Western-style cafes throughout the city, Woolloomoolo stands out from the pack through specialties like Aussie meat pie and Greek moussaka. Avoid the lunch rush on weekdays, when Woolloomoolo transforms into a sophisticated cafeteria, with crowds of nine-to-fivers squeezed around the tables to take advantage of the hearty lunch specials. Patio seating is also available at the Xinyi location, a perk rarely seen in Taipei eateries. When weather permits, enjoy a flat white made with imported Aussie beans while sitting in the sunshine. 886/(0)2-8789-0128 (Xinyi Store)

Islands trace the Great Barrier Reef up the northeastern coast of Australia, clustering in the clear blue waters known as the Whitsundays. There, nestled on Hamilton Island, Qualia has set a new standard for Australian tourism—and resorts worldwide. What is magical about Qualia, however, is not just the champagne on arrival, or the fact that some rooms have their own plunge pools. The winning feature here is how perfectly the resort fits into the natural beauty of the island, almost disappearing into the eucalyptus trees of the surrounding rain forest. Understated and sophisticated, Qualia fosters a sensitive connection to the environment, allowing guests to experience Australia without all the usual tourist fanfare.

Rooms look through natural bushland out to the water and surrounding islands, where dolphins are frequently spotted. They also come with their own electric golf carts, which guests can use to tour the entire island. In the epic Long Pavilion, floor-to-ceiling windows on the seaward side open to an infinity pool, while glass windows at the other end offer views of the resort’s bright tropical landscaping.

Find cool pieces by an array of new and noteworthy Australian brands at this small concept store, founded to showcase independent designers in an artistic shopping environment. The Melbourne space stocks a monthly edit of men’s, women’s, and children’s clothing, with original and limited-edition pieces by around 100 local lines. With so many unique options on offer, you’ve got an excellent chance of finding something that perfectly suits your aesthetic, be it a little black dress by Ella Fashion, or attention-grabbing earrings by Plain Janes. If you can’t find what you’re looking for downtown, you can always check out the other Design a Space locations in Fitzroy and Windsor—the selection is different at each store.

Founder’s Note: Uncommon Travels

The craft cookies, cakes, and ice cream churned daily here from local milk and fruit are as creative as they come. Ask for a nostalgic Australian treat, and you might be offered a Mit Mat (a ganache-filled play on the Tim Tam), a Ro-Vo (a room-temperature spin-off of an iced VoVo), or a Jatz pie (like a caramel slice topped with a mosaic of Arnott’s Jatz crackers). The bloke behind the brilliance is none other than Alistair Wise, son of cookbook author Sally Wise, who spent a stint working with Gordon Ramsay. This emporium of happiness—and envy, to be sure—also whips up scrumptious savories including a mean scallop pie and a buttery poached chicken “sanger” with bacon, lettuce, hummus, mayo, and hard-boiled egg.

North of the harbor on Lavender Bay, Clark Park is an ideal spot for a picnic away from the bustle. On the western end, curious visitors discover the garden Wendy Whiteley created from a landfill. 5- to 10-minute walk from Luna Park. This appeared in the August/September 2013 issue.

In the country’s wine region, you can pick grapes, sing songs, and keep ancient harvest traditions alive. It’s so much fun, you can taste it.

In a square mile of West Texas, Chris Colin finds family and traces his roots back to a wilder America.

Young artists stake their claim to the city’s open spaces.

Following the lead of mixed-use space Deus ex Machina in Camperdown, Rising Sun is a motorcycle workshop cum café and restaurant built for the Newtown community. That means garage space with tools and repair bays for members as well as regular workshops (one just for women), art events, and a public night ride on the last Tuesday of the month. Then there’s the rustic-chic café that whips up Asian-fusion cuisine that’s as rootsy and beautiful as the bikes. Come in the morning for breakfast ramen—bacon, roasted tomatoes, and a fried egg floating in bone broth—and a Japanese twist on a bloody mary. Then return for creative tapas and share plates in the evening complemented by a stellar list of Australian beers and wines.

An Aboriginal territory turned shipping port between the Rocks district and King Street Wharf has been transformed into a harborfront reserve, modeled after what the headland may have looked like before Europeans arrived. It’s a great area for a walk or a picnic as well as for special events. And the surrounding area is home to dozens of new bars and restaurants. The seafood-centric Cirrus is run by the award-winning Bentley Restaurant team, and 12-Micron celebrates Australian produce through a menu organized around the elements. Early birds flock to cult favorites Micro by Coffee Alchemy and Bourke Street Bakery, while the after-work crowd unwinds at Sydney’s first vermouth bar, Banksii; the tropical rooftop Untied; and Smoke bar, on the top level of Barangaroo House.

Chef Bill Granger started his first restaurant in Darlinghurst at age 24. Since then, his sunny Aussie eatery (most famous for its creamy scrambled eggs, ricotta hotcakes, and crunchy corn fritters) has spread to Surry Hills as well as Honolulu, Seoul, London, and four locations in Japan. The newest Australian outpost of Bills in Bondi Beach is bright and communal, spilling out on to one of the area’s most lively streets. Arrive early to avoid the long queue for weekend brunch, and sample everything from house-cured gravlax to the fried rice bowl with kimchi. Dinner (at the Bondi and Surry Hills locations only) is a more intimate, candle-lit affair, with interesting Aussie-Asian plates like tea-smoked trout salad, fish curry, spicy pork belly, and Japanese-style steak.