Travel

Before she had even left, Tiffany Dowd was planning her next couples escape to The Brando, an exclusive resort on its own private atoll in the South Pacific. “I kept asking my husband over and over when we could come back,” the global luxury hotel expert shared. During their stay in a beachfront villa, with its private infinity pool and outdoor soaking tub, Dowd and her husband snorkeled, enjoyed spa treatments, and took part in Polynesian cultural activities (she learned to palm weave; he learned to play the ukulele). “It’s one of the few places in the world I have truly felt away from it all,” she remembered. “You feel like you are in a postcard-perfect setting and it’s just the two of you.” Although it’s not just the two of you, of course. The Brando has 35 villas catered to by a staff of 200. However, good design — and that whole private island aspect — make everything and everyone else drift away. “The Brando feels like a once-in-a-lifetime experience that you must experience again and again,” Dowd added.

Monique became a Sydneysider (yes, that’s what they call themselves) when she was five. She’s lived all over the world but came home in 2005 because, well, Sydney is simply the most beautiful city in the world. With its drop-dead gorgeous coastline, stunning harbour, and thriving arts, music, and foodie scenes, who’d want to live anywhere else?

Take revolutionary architecture, award-winning cuisine, an outsized musical legacy, and top-flight museums, and wrap them all up in an easy-to-navigate package. Now throw in a population of locals at once cosmopolitan and brimming with Midwestern good humor. That’s Chicago, a city that will roll out the welcome mat and keep you engaged whether you plan to stay a night or a month.