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The brick-and-iron warehouses of the old Eveleigh Railway Workshops host a diverse lineup of experimental music, theater, film, and fine art. Located on the border of Redfern and Waterloo, Carriageworks was restored to keep the historical roots intact while providing a space for cutting-edge culture. Every Saturday, more than 70 stalls fill the former railyard outside with organic produce, artisan breads, specialty coffee, and exotic flowers as well as street food from the likes of chef Kylie Kwong during the farmers’ market. Fuel up at the market and then get inspired by whatever is on display inside this artist-run venue. Big annual events for Sydney Contemporary, Pacific Runway, Sydney Gay and Lesbian Mardi Gras, and the Sydney Festival are also held here throughout the year.

Owned by Terry Kaljo—a former model and founder of the Contemporary Hotels collection of upscale rental homes and villas—the Medusa Boutique Hotel offers 18 unique accommodations in Darlinghurst, an eclectic area and the epicenter of Sydney’s gay community. The 19th-century home is filled with wacky touches, from red Alice in Wonderland–style carpeting that runs up the grand staircase to pastel-pink walls studded with maple leaves in the entryway. The midcentury-modern rooms—with their retro primary colors, geometric patterns, and vintage chaises longues—attract fashion, media, and design professionals looking to get beneath the surface of one of Sydney’s liveliest neighborhoods. But there’s still the opportunity to relax, as guests can settle in next to the fireplace in the lobby to read the newspaper, enjoy a complimentary pastry, or make new friends. Longtime staff members offer the kind of local knowledge and personal attention that keeps guests coming back.

Between 15th and 16th streets on Ninth Avenue in Chelsea, the Chelsea Market is a food court with New York attitude. Its restaurants and shops sell Australian meat pies, banh mi, and lobster rolls. These are no fast-food chains—this is a place to find cheese from upstate or that spice you can’t find at your supermarket. There is now a Posman Books and an Anthropologie outpost, but most of the places here stay true to the market’s culinary roots with Sarabeth’s, Ronnybrook Dairy, and Berlin Currywurst as good places to pick up food to eat on the spot or to take home. If you are looking for a hard-to-find kitchen gadget, the Bowery Kitchens store is almost sure to have it. The market is also ideally located if you want to purchase picnic supplies before ascending to the High Line if the weather is good.

Set in a tropical garden in the suburb of Fannie Bay, this superb museum and gallery is the best place to learn all about the art, history and culture of the Top End (the nickname for this northernmost section of the Northern Territory). The excellent collection of indigenous art includes both traditional and contemporary works. One gallery is devoted to the tragic events of Cyclone Tracy, the natural disaster of 1974; another covers the boats of the Pacific Islands. The museum’s most popular exhibit may well be Sweetheart: the stuffed carcass of a five-meter (16-foot) male saltwater crocodile that once terrorized the billabongs (waterways) outside Darwin.

Named for the wife of Governor Lachlan Macquarie, who presided over New South Wales in the early 1800s, this site provides one of the most spectacular views in town. Find the historic carved-rock ledge in the Royal Botanic Garden, east of the Opera House, where you’ll drink in a vista encompassing the Bridge, harbor and distant mountains, along with historic sites like Kirribilli House (the prime minister’s residence), the island of Fort Denison and the Navy Dockyards at Woolloomooloo.

The gallery, boutique, and tearooms of Morocco’s most famous living artist, Hassan Hajjaj, is an essential stop for any art lovers staying in the city. Tucked away down a narrow alley behind the Rahba Lakdima (otherwise known as the Place des Épices), it’s like stumbling into a jewel box filled with pop-art treasures. Hajjaj made a name for himself with a series of photographs titled Kech Angels, which depicted local girls on mopeds dressed in eye-popping robes. The collection has been exhibited all over the world in such illustrious venues as the Victoria and Albert Museum in London and the Institut des Cultures d’Islam in Paris, but nowhere beats enjoying the work on home turf. While you’re there, treat yourself to his iconic recycled home and fashion pieces, such as a sardine-can lantern, a pair of babouches (Moroccan slippers) cut from a flour sack, or a stool from an oil drum. And if you hang around for a pot of mint tea in the courtyard, you might even meet the man himself.

One of the most fun places I dined at in Italy was Il Latini, in Florence. It’s in a large, maze-like building with aged prosciutto hanging from the ceilings, and art collaged upon the walls. Seating is at communal tables, and at times it felt like we were all at a wedding. In our case, my boyfriend and I sat with another couple from Australia, who were beginning their tour of Italy, but it’s easy to meet locals at this spot, too. The waiters and the owner are very persuasive when it comes to traditional Florentine food. I requested half of a Florentine steak, but I am sure I was given a full one—one of the largest I have ever seen served. It was cooked rare, and was extremely tender and flavorful. However, I am not much of a carnivore, and as such, my favorite part of the dinner was the fresh sage ravioli. After our meal, the waiter kept bringing shots and wine, which appeared to be on the house. There are no exact prices, and the waiter determines your meal’s cost.

This two-level Cantonese palace—connected by an escalator—is lined with tanks of live fish, crustaceans, and bivalves, which the staff will stir-fry, steam, salt-and-pepper, and douse in XO sauce to your heart’s delight. There are many reasons the Chinatown establishment is beloved among in-the-know locals and hospitality veterans, and they extend from the warm, welcoming service all the way through the exquisite live abalone sashimi, mud crab hot pot, and private reserve range of wines. For a Chinese food adventure, arrive late (this place is open until 4 a.m.) and order straight from the live tanks. At least, that’s what the rock stars, politicians, and CBD chefs just getting off work do.

An indigenous-owned art gallery located at the busy junction of the Arnhem and Stuart Highways a half hour outside Darwin, The Didgeridoo Hut prides itself on selling genuine Aboriginal artwork from remote Top End communities, with whom the owners Dennis and Janis have personal relationships. In fact artists often come to the shop to demonstrate their painting and didgeridoo making skills and to share their stories with visitors. The works on display are high-quality and overwhelming; thankfully, the friendly staff are very knowledgeable about the artists and their symbolism—spiral circles represent waterholes and tool imagery usually stands for a man or woman. The prices are fair, but some have a little bargaining room built in.

Opened in time for the 2000 Sydney Olympics, the Establishment is a pioneering 31-room boutique hotel housed in an 1890s steel plant near the modern-day stock exchange building downtown. Managed by the hospitality group Merivale—which started as a fashion house specializing in fascinator hats and mini skirts—the hotel is popular among brand executives who book the 328-square-foot Loft Penthouse for product launches and photo shoots. Rooms feature wood furnishings, swinging metal doors, animal hides, and suedelike daybeds as well as such amenities as Apple TV, Bose surround sound, and Lululemon yoga mats. Bathrooms are particularly luxurious here, with marble floors, freestanding tubs, Bulgari products, and tall windows that open up to Sydney’s bustling business district. The best part about the Establishment, though, is the internal access it offers to some of the city’s hottest bars and restaurants, which are housed within the same complex as the hotel. And after enjoying live music and a few stiff cocktails at the speakeasy Palmer & Co, guests are welcomed to bed with Sleep Tight tea and a homemade chocolate chip cookie.

Chiseled from a sandstone-and-brick wool factory on the site of Sydney’s first hospital, the Harbour Rocks Hotel is one of the most historic accommodations in the Rocks—and maybe the most haunted. Hotel staff say part of the building, named Scarlett’s Cottages after a well-known lady of the night, is watched over by Eric, a man who once lived here and who still searches for Scarlett in the labyrinthine corridors after she swore her love to him and then disappeared. Ghosts aside, the hotel’s 59 rooms are peaceful, with high ceilings, Georgian arched windows, brick walls painted dark gray, Old West–style textiles, and wool carpeting that recalls the building’s former life. The place is filled with fun artifacts, too, from the ancient luggage lift to old maps and letters framed on the walls. The early-20th-century history that pervades the building is also found in every direction outside its doors.

The Carrington’s long and rich history spans nearly 125 years since her opening by Sydney hotelier Harry Rowell. Originally named The Great Western, this Grand Old Lady soon became a popular retreat for international guests, Sydney’s elite, and adventurers eager to explore the Blue Mountains’ natural wonders. The hotel is steeped in history, tales of adventures and royalty, and perhaps even a ghost tale or two. The walls are covered with vintage photographs and the place looks like it was sealed in a time capsule (and yet still boasts modern amenities like wifi). The hotel bar is vintage, perfect for a glass of wine or local pint after a long day of adventures in the Blues. There are function rooms, a pool table, an elegant dining room (plus a more casual dining establishment, which used to be the town bank, on the property, as well as a stand-alone pub), as well as a 100-year old regulation snooker table. An onsite bottle shop is available, offering a wide variety of gourmet foods and excellent beers and wines, and a brewpub is even in the works.

There is a sliver of Africa where four countries almost converge: Zambia, Zimbabwe, Namibia and Botswana. The Chobe River is one of the many separation points between Botswana and Namibia and it’s also where I experienced one of my favorite wildlife adventures of all time. The boat I called home for a few days is permanently moored in the middle of a vast river system of wetlands and river grasses. The marshland is rich in wildlife; hippos, birds of all kinds, Cape Buffalo and hundreds of elephants converge on this one spot. The elephants were perhaps the most impressive, in size as well as sheer numbers. While boating along the river one day the driver shushed us, cut the engine and pointed to the riverbank. There on the shore were two young elephants walking with great purpose towards the water. I had never thought about whether or not elephants could swim , but I soon got my answer. They plunged into the river without fear and began to swim with zeal and power to the coveted river island. They also didn’t seem to care about us as they came within a few feet of our boat. Watching these majestic animals ford the river and then emerge with a great splash was extraordinary. It’s one of the travel moments that makes you feel both alive and incredibly thankful.

Following the success of its first hotel in the vibrant Shoreditch neighborhood, The Hoxton group opened this second outpost in 2014 in the less “happening”—but super-central—Holborn area, just a short walk from the British Museum, Covent Garden, and The Strand. Set in a former telephone exchange building (part of which is historic Victorian, the other part mid-century concrete), the hotel encourages socializing and working in its open-plan lobby, which is outfitted with library-style wooden tables, book-lined shelves, retro couches, and a couple of guest-use computers, plus plenty of places to plug in. You can order drinks and coffee all day in the lobby, three meals of large-portioned favorites (from fish and chips and burgers to banana splits) in the industrial-chic Hubbard and Bell restaurant, and rotisserie chicken and sides in the speakeasy-feeling basement Chicken Shop.

These communal spaces come in particularly handy if you’ve checked in to one of the smaller rooms—the 174 accommodations come in sizes from Shoebox and Snug to Cosy and Roomy (which is not all that much bigger). The spaces are cleverly designed to feel larger than they are, though, with large, circular mirrors, bespoke wallpaper printed with Charles Dickens scenes, comfy beds, and artwork by students of the prestigious Central St. Martins university. There are also useful perks like free Wi-Fi and one hour of international calling, a light breakfast delivered to your door daily, complimentary water and milk in the mini-fridge, and beer and wine available at the front desk for regular grocery store (not hotel) prices. If you want to linger, late checkout is available for an additional £5 per hour.

Scattered with Victorian mansions, St. Paul’s tree-lined Summit Ave. is one of the most beautiful residential streets in the Midwest, with famous former residents including author F. Scott Fitzgerald and early railroad entrepreneur James J. Hill. Guided tours are offered from the James J. Hill House Wed–Sun, but it is also a worthwhile independent stroll. Make sure to start or end at the gorgeous St. Paul Cathedral, overlooking downtown St. Paul.