Uncover the hidden gems of Sydney through the eyes of designer Henry Holland, who shares his favorite activities and dining experiences in this captivating Australian city.

Sydney, Australia, has been a muse for designer Henry Holland for nearly two decades. His bond with this vibrant city goes beyond mere professional ties; it’s a passionate affair nurtured by its lively lifestyle, stunning landscapes, and cherished friendships. In his insider guide, Holland unveils the best Sydney has to offer, from breathtaking beaches to exquisite dining experiences.
The Allure of Sydney
Holland first set foot in Sydney nearly 20 years ago, initially drawn by work commitments. Since then, the city has morphed into a second home. “I’ve met so many people who I consider friends for life,” he shares, emphasizing the connections that keep him coming back.
But it’s not just the people; the city’s outdoor lifestyle resonates deeply with him, especially as he approaches his fifth decade, making the idea of living there more appealing than ever.
During a recent visit in April last year, Holland launched a ceramics line at Jardan, capping off the event with a lively night out.
“It was one of my shortest trips at just 36 hours, but I felt at home as soon as I landed,” he recalls, highlighting Sydney’s welcoming atmosphere that feels like a warm embrace.
Top Recommendations for a Perfect Day
Want to explore Sydney like a local? Holland’s itinerary is your golden ticket. He kicks off his day at Camp Cove, where a sunrise swim sets a refreshing tone. “It’s a tiny little beach with a great coffee hut right on the sand,” he notes, the perfect spot to grab a caffeine fix before diving into the day’s adventures.
Next up is the iconic Bondi to Bronte coastal walk, offering breathtaking ocean views and opportunities for a quick dip at Bronte Pool. “In the afternoon, I’d mooch around the shops in Paddington and maybe head into the city to visit the Powerhouse Museum,” he adds, highlighting the blend of culture and leisure that defines a day in Sydney.
When it comes to dining, Holland recommends Bert’s Bar and Brasserie, easily accessible via a scenic water taxi. “The setting was just perfect—almost as good as the lobster and martinis,” he recalls, showcasing Sydney’s vibrant culinary scene. And don’t miss Icebergs at Bondi Beach, known for its festive vibe and stunning views. “Every year, they throw a legendary New Year’s Day party there,” he hints, giving a taste of the city’s lively spirit.
Nightlife and Relaxation
As the sun dips below the horizon, Sydney’s nightlife springs to life. Holland suggests kicking off the evening at Bar Freda’s at The Abercrombie, where dinner leads into a night of dancing. “I’m always there to see my friends Hamish and Trent,” he shares, underscoring the social connections that make his Sydney experience unforgettable.
Shopping is another highlight for Holland, particularly at P Johnson in Paddington, known for its stunning menswear. “They have their own line of tailoring and shirting, which is fantastic,” he notes, seamlessly blending fashion with local culture.
Evenings might also include a casual stroll along the cliffs of Tamarama Beach, where surfers catch waves against a backdrop of spectacular ocean views. Holland finds this experience truly magical, especially during the whale migration season—imagine witnessing those majestic creatures up close!
Essentials for Every Visit
When packing for Sydney, Holland emphasizes the importance of workout clothes and swim gear. “I was never very keen on swimming in the sea until I spent more time in Sydney, where it’s practically a daily ritual,” he admits. No matter the season, he recommends bringing beach outfits since the city’s warm climate makes beach outings a year-round affair.
For those eager to maintain their fitness, Holland suggests joining locals for Pilates or early morning runs. “Nothing says I’ve arrived in Sydney quite like a run past the iconic Opera House,” he asserts, perfectly blending fitness with sightseeing, which is a hallmark of the Sydney lifestyle.
In conclusion, Henry Holland’s insights offer a comprehensive guide for anyone looking to embrace the vibrant lifestyle of Sydney. From sunlit swims to lively nights out, the city beckons with endless opportunities for adventure and connection. Are you ready to dive into Sydney’s charm?
