Luxury Holidays to Sydney
Harbour Glamour and Coastal Cool Collide
Sydney is where iconic luxury meets laid-back lifestyle. Think sunset sails, beachfront brunches, and skyline views from designer suites—all wrapped in that effortless Australian ease.
With the Sydney Opera House, Bondi Beach, and world-class restaurants at your doorstep, this is the city where luxury isn’t just an experience—it’s a way of life.
Awake & Wander crafts bespoke Sydney escapes that blend urban sophistication with natural splendour, from private yacht charters to helicopter flights over the harbour and exclusive access to the city’s finest cultural offerings.
A Small Selection of our Latest Offers to Sydney
These latest offers have been generated through our online booking system which is powered by our sister company , Jamie Wake Travel, and using our handpicked suppliers.
There will occasionally be times when offers will not show here. For example, where a destination may require more in-depth travel arrangements and will need to be tailor made by our team.
Prefer a more personal touch? We're always here to tailor your journey—simply get in touch and let us create the perfect luxury holiday to Sydney for you.
Arriving in Sydney: Your Stylish Gateway to Australia
Sydney’s Kingsford Smith International Airport (SYD) is the country’s main international hub, with direct flights from London, Singapore, Los Angeles, and more. Awake & Wander arranges VIP immigration services, chauffeured transfers, and scenic helicopter rides for guests heading straight to their luxury city hotel or coastal hideaway.
When to Visit Sydney to Experience Peak Urban Chic
Sydney shines year-round, but the best months are October to April—ideal for beach days, alfresco dining, and warm evenings on the harbour. The Sydney Festival in January, Vivid Light Festival in June, and springtime blooms in the Royal Botanic Gardens are highlights. Awake & Wander matches your visit to the city’s cultural calendar, ensuring every moment counts.
The Top 4 Unforgettable Experiences and Things to Do in Sydney
Sydney’s magnetism lies in its contrasts—glamour and surf, skyline and sandstone, celebration and calm.
1
Cruise Sydney Harbour on a Private Superyacht
See the Opera House and Harbour Bridge from the water with champagne in hand. Awake & Wander arranges luxury yacht charters complete with private chefs, secluded swimming stops, and sunset cocktails as the skyline glows.
2
Take a Seaplane to a Secluded Beach Restaurant
Fly above the coast in a classic seaplane to Palm Beach or Berowra Waters Inn, landing right by the water’s edge for a gourmet lunch. This is Australia’s answer to the Riviera—and one of Sydney’s most memorable indulgences.
3
Explore Bondi with a Personal Wellness Guide
Sydney’s coastal lifestyle is best lived in Bondi, where you’ll stretch into sunrise yoga, enjoy organic beachside brunch, and walk the cliffs with a local wellness coach. It’s wellness, Sydney-style: natural, nourishing, and deeply stylish.
4
Discover Aboriginal Culture in Luxury Contexts
Explore First Nations history through private art gallery tours, bush tucker tastings, and walks with Indigenous guides in the Royal National Park. Awake & Wander elevates cultural travel with respect, depth, and luxury.
Why Sydney Is the Ultimate Luxury City by the Sea
Sydney blends natural beauty with refined living. It’s a place where you can go from designer boutiques to dolphin-spotting within an hour—and finish the day with fireworks above the harbour.
Awake & Wander designs Sydney stays that capture the city's rhythm and romance, from private art showings to rooftop pool suites. Come for the icons—stay for the spirit.
