Sydney, the vibrant heart of New South Wales, welcomed us for a family travel adventure with its signature blend of urban energy and natural beauty. Despite the rainy skies, our weekend in this iconic city was nothing short of inspiring, filled with tailored experiences that showcased Sydney’s charm and character. As a private travel advisor specializing in custom itinerary planning, I crafted a seamless journey that balanced immersive travel experiences with the practicalities of navigating Sydney with teens.
Friday: Settling into Chinatown
Our arrival in Sydney was effortless, thanks to the Four Points Sheraton, perfectly situated in Chinatown near the University of Technology Sydney. The hotel’s location made exploring the city simple, and its balance of comfort and value set the tone for our stay. After settling in, we wandered through Chinatown’s lively streets and indulged in authentic travel experiences, including a flavorful dinner at A Bowl of Noodles. The soup dumplings and pork dumplings were a hit with all, and the savored bao and stir-fry dishes were the perfect main courses
Saturday: Markets, Harbour Views, and Hidden Gems
The day began with a visit to The Rocks Market, where we discovered Sticky, a candy store that delighted us with its handmade treats. Watching the candy-making process was mesmerizing, and the delicious creations were a perfect souvenir from Sydney.
Next, we embarked on a lunchtime harbour cruise with Princess Harbour Cruises. Even under overcast skies, the views of Sydney Harbour were beautiful from every angle. The luxurious waterfront homes and the city’s skyline reminded us of our time in Seattle, blending urban sophistication with natural beauty.
In the afternoon, we found ourselves at Handpicked Wines Cellar Door, a family-friendly winery where we relaxed over a wine flight and played games with the girls. This tailored experience was a perfect way to unwind before strolling through Darling Harbour, visiting Tumbalong Park, and exploring the serene Chinese Garden of Friendship. Dinner at WingBoi was a highlight, with its lively atmosphere and premium flavors that the kids adored…in fact, the kids still talk about the food and vibe there, so it was memorable!
Sunday: The Blue Mountains Adventure
Sunday was dedicated to exploring the Blue Mountains with Feel Good Nature Tours. As a destination expert for Australia, I knew the importance of choosing a boutique tour operator like Feel Good! Nature Tours, whose small group size and personalized approach ensured an enriching experience. Craig, our guide, delivered concierge-level service, navigating the foggy weather to reveal breathtaking views and hidden gems. This is not your “cookie cutter” tour, as he adjusted and managed our itinerary to match the ever-changing weather and ensured we experienced the majesty of the Blue Mountains.
After making our way to the Blue Mountains, we first started with a hearty meat pie and coffee from Mountain High Pies. The steak, mushroom, and Guinness hand pie was our favorite, but every one we tried was delicious (as we all made a different pick). The Banoffe Tart sweet pie was the perfect touch at the end of our lunch.
Craig tailored every stop on his tour—from Govett’s Leap to the Wind Eroded Cave—to showcase the region’s beauty. The Megalong Valley offered a once-in-a-lifetime encounter with wild kangaroos. Mountain High Pies provided a memorable lunch with flavors like Lamb, Rosemary, and Shiraz. Craig’s expertise and flexibility transformed a rainy day into an immersive adventure, earning high praise from our 15-year-old daughter, who declared it the best tour of the trip.
Monday: Bucket List Moments
We packed our final day in Sydney with unforgettable bucket list experiences. The morning began with pastries and coffee at Bondi Boulangerie, where the Nutella croissant was a standout. Then, it was time for the Bridge Climb—a transformative journey that offered panoramic views of the city and harbor. BridgeClimb Sydney meticulously plans each ascent, emphasizing safety and storytelling to create an unforgettable experience. Even on overcast days, the views impress, making the climb a true bucket list adventure – thankfully our climb avoided the weather which provided us with spectacular views of Sydney from every direction!
Afterward, we enjoyed lunch at the Harbour View Hotel, savoring fish and chips and burgers before heading to Bondi Beach. Despite the rain, Bondi Icebergs Swim Club provided a cozy retreat with cocktails for the adults, mocktails for the girls, and our favorite dice game (Qwixx). We enjoyed watching surfers braved the icy waters of the ocean and swimmers brave the icy waters of the Swim Club. A scoop of gelato from Gelato Messina capped off the afternoon, though Anita Gelato near our hotel remained our favorite.
We spent our evening exploring Spice Alley, where we indulged in chocolate-covered strawberries and bougie hot chocolate. For dinner, we opted for the warmth of Andiamo Trattoria, a fitting end to our Sydney adventure.
Navigating Sydney with Teens
Traveling with teens can be a rewarding challenge, and Sydney proved to be an ideal destination for creating memorable moments. Insider tips for Sydney include choosing accommodations near public transportation for effortless exploration, incorporating interactive experiences like the Bridge Climb, and balancing adventure with downtime at family-friendly spots like Handpicked Wines Cellar Door.
Reflections on Sydney
Sydney’s blend of urban sophistication and natural wonders left us inspired. From the tailored experiences in Chinatown to the enriching adventures in the Blue Mountains, every moment was crafted to be memorable. The city’s rain-soaked charm reminded us of Seattle (a city we called home for 2.5 years) and the pace and buzz had us feeling some similarities to NYC. That said, its lovely harbour, natural beauty of beaches and mountains, world-famous landmarks, and multicultural vibe made it uniquely Sydney.
As a travel planning consultant, I specialize in crafting seamless journeys that balance immersive travel experiences with practical considerations, ensuring every trip is tailored to my clients’ needs. If you’re wondering how to plan a trip to Sydney or looking for insider tips on navigating Australia with kids, WonderCrafted Travel is here to help.
