How I Holiday: A Chic Melbourne Couples’ Guide To The Big Apple
Emma Bishop
Head Of Content: Features And Lifestyle | Urban List
Welcome to How I Holiday, a series of travel stories and recommendations shared by friends of Urban List from Aotearoa and Australia.
Penny Gibson, creative director and founder of content biz Pene Lope Studios, and Paddy Whelehan are one chic couple. When the duo aren't working on their many creative pursuits in Melbourne, they're jet-setting to source inspiration in the Big Apple. For the pair, New York is a city that does the work for you. There are endless bars and art galleries, the people watching is elite, and the nights only end when you run out of energy.
Why is New York special to you?
New York is special to us because Paddy lived there before travelling to Australia, and coming back together feels like stepping into his old world with fresh eyes. We get to meet up with old friends, hit up familiar spots, explore the city in new ways, and mix in a bit of work by catching up with other brand owners and designers/makers to talk about potential collaborations.
We always love to do a photoshoot too, because filming and shooting there feels so effortless—the city does most of the work for you.
What’s a core memory you have from a trip there?
A core memory is our late nights at Balthazar, where the food and cocktails never miss. We always seem to make new friends there, and the people-watching is unbeatable. Those nights stretch out in the best way, as if the whole place slows down just enough to enjoy every moment. It’s become the spot we return to whenever we want to tap back into that unmistakable New York feeling.
Where should people eat, drink, stay and play when visiting?
We always recommend the Lower East Side, with Untitled at 3 Freeman Alley as our go-to for its warm staff and perfect location.
Pair that with a Blank Street matcha, endless bars and galleries to wander through, and—if you can manage it—a night at The Box for an experience you won’t forget. The area has a rare mix of grit and refinement that keeps it interesting no matter how many times you visit. You can arrive with no plan and still end up exactly where you’re meant to be.
Explore more of How I Holiday:
- How I Holiday: Melbourne Musician Harvey Sutherland Shares His Go-To Taco Trucks And Diners In LA
- How I Holiday: Beluga Caviar And Vintage Chanel—An Interior Architect’s Paris Picks
- How I Holiday: Mrs White’s Joyful Family Photos Will Inspire Your Next Japan Getaway
What’s the best meal you’ve ever had in New York?
The best meal we’ve had is at Monkey Bar, home to a cult-classic cheeseburger. It’s one of those meals where everything—the atmosphere, the service, the simplicity done perfectly—comes together so well that you think about it long after you’ve left. It’s the kind of spot that makes you consider going back the very next night.
What’s the best event on New York’s cultural cal?
Halloween in New York is unmatched, with the whole city turning into a creative, electric, fully committed celebration that we look forward to every year.
Coming from Australia, where it’s barely celebrated, it feels completely different and even more exciting paired with the cooler weather. The energy is infectious—people don’t just dress up, they become their characters. The entire city feels like one giant, living film set.
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