The Tailor Destinations

Sydney

The capital of New South Wales

Sydney is Australia’s oldest, largest and busiest ocean-side city metropolis

Sydney is an iconic and instantly recognisable city perched on the East Coast of Australia. It is home to outstanding beaches and waterways, an interwoven backdrop of Aboriginal and colonial histories, world-recognised landmarks, and a vibrant cultural life. With so much on offer within the city and within its surrounds, Sydney is a must-see destination on any Australian journey.

  • Highlights
  • What We Offer
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Highlights

Destination Highlights

  • Experience Sydney from a local’s point of view with expert tours – surf Bondi, walk the local suburbs, or bike bush landscapes with premium hosting curated to your interests.
  • Enjoy behind-the-scenes access to internationally recognised icons: climb the Sydney Harbour Bridge and admire the skyline from a 360° angle, and go behind the scenes of the Sydney Opera House.
  • Wine and dine your way through the country’s most exclusive and premium options, found in stunning locations offering exquisite views of the Harbour and beyond.
Our Experts

What do our experts say about Sydney?

Sydney sparkles! Such a vibrant and happy city, there is a constant positive energy throughout the city and the harbour is at the heart of it all! Discover the harbour on foot, explore secret scenic walks and reward yourself with a picnic in one of the beautiful parks.

Amanda Fisher
Senior Travel Designer AT THE TAILOR

What do I love about working at The Tailor?

I love sharing the knowledge that we have collectively gathered over years and years of selling Australia – each one of us regularly comes up with new combinations and twists on itineraries and destinations that we share with one another. With the help of our fabulous product suppliers we ‘invent’ new experiences that enable our guests to delve deeper in Australia. I love the magic that we add to every itinerary … something special, perfectly formed and ‘tailored’ to suit the traveller.

City or Wilderness? Why and where?

Wilderness and for two reasons …. One is because I love the big sky country, I love places where you can see from one edge of the earth to the other. Where the sky is literally half of everything and it is usually as blue as can be. I also love being in the wilderness because we have so much to learn about our continent’s unique history, flora, fauna, bio-diversity, the conservation challenges we face and the Aboriginal people’s amazing connection to country.

What We Offer

Accommodation and Experiences in Sydney

  • Effortlessly combining the best traits of a chic city hotel and prestigious villas, complete with signature restaurants and a luxurious spa, the Crown Towers Sydney is a five-star sanctuary in the heart of the world’s most famous harbour city. Designed by award-winning British architecture firm Wilkinson Eyre, the Crown Towers twists and melds into the skyline, offering a distinctive silhouette against the city skyline and ensuring each room is connected to the city’s beautiful surrounds.

    Crown Towers Sydney
  • As far as Harbourside views, Park Hyatt Sydney can claim to be unrivalled. Located near the foot of the South Pier of the Sydney Harbour Bridge and facing directly towards the Opera House, it is quite literally in the heart of Sydney’s glamorous, vibrant Circular Quay and Rocks district. A true five-star luxury hotel, it has recently undergone its largest and most comprehensive transformation in its 21-year history.

    Park Hyatt Sydney
  • Taking pride of place in Sydney’s commercial, arts and cultural hub, the Capella Sydney is an enviable new luxury offering in the heart of the harbour city’s lively CBD. Housed in an intricately restored heritage-listed building that was initially developed in the early 1930’s, this beautiful hotel balances storied architectural features with a light-palleted contemporary design aesthetic. Capella Sydney has been designed to indulge guests with luxurious accommodation, world-class cuisine, and cultural immersion.

    Capella Sydney
  • Offering multiple tour types over four discrete timeframes ranging from dawn to dusk, and with tour lengths ranging from 2.5 – 3.5 hours, there’s a Bridge Climb experience for all kinds of travellers. Led by informative and fun guides, you’ll discover the major landmarks, be enlightened with local history and knowledge, and marvel at magnificent views stretching across all of Sydney to as far as the Blue Mountains on a clear day.

    Bridge Climb Sydney
  • Local Eyes’ Sydney are a small group and private charter business supplying a beautiful collection of unique and interactive day tours around iconic Sydney and the greater New South Wales’ area. Each experience combines intimate knowledge of exceptional local Sydney destinations and experiences.

    Local Eyes
Featured itineraries

Journeys featuring Sydney

Our carefully curated itineraries offer unrivalled access to Australia’s most sought-after people, places, and experiences, often unseen by most. Through our deep connections and expertise, we unlock private moments in the country’s rarest destinations, blending adventure, luxury, and culture into seamless, one-of-a-kind journeys designed to inspire and captivate.

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The Tailor’s Timeless Journey – Our Most Popular Australian Adventure

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Experience the best Australia has to offer on this luxury 14-day itinerary to the country’s most remarkable and exciting destinations.

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Red To White Sands

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Sydney, Safari, Reef & Shiraz

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Southern Safari in Style: Sydney, Lord Howe Island, Melbourne and Tasmania

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Wildlife, Outback & Reef

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The Tailor’s Timeless Journey – Our Most Popular Australian Adventure

17 days

Travel Australia like a Rockstar

14 days

Around Australia in 14 Days

Experience the best Australia has to offer on this luxury 14-day itinerary to the country’s most remarkable and exciting destinations.

28 days

Iconic Australia – Sea, City and Culture

10 days

Red Centre to Reef

14 days

Reef, Rainforest and Wildlife: A Family Itinerary

13 days

Red To White Sands

10 days

Off the Beaten Track in Style: A Top End Itinerary

14 days

Australia’s Best Adrenaline Adventure

14 days

Sydney, Safari, Reef & Shiraz

13 days

Southern Safari in Style: Sydney, Lord Howe Island, Melbourne and Tasmania

12 days

Wildlife, Outback & Reef

14 days

The Tailor’s Timeless Journey – Our Most Popular Australian Adventure

17 days

Travel Australia like a Rockstar

14 days

Around Australia in 14 Days

Experience the best Australia has to offer on this luxury 14-day itinerary to the country’s most remarkable and exciting destinations.

28 days

Iconic Australia – Sea, City and Culture

10 days

Red Centre to Reef

14 days

Reef, Rainforest and Wildlife: A Family Itinerary

13 days

Red To White Sands

10 days

Off the Beaten Track in Style: A Top End Itinerary

14 days

Australia’s Best Adrenaline Adventure

14 days

Sydney, Safari, Reef & Shiraz

13 days

Southern Safari in Style: Sydney, Lord Howe Island, Melbourne and Tasmania

12 days

Wildlife, Outback & Reef

Contact us

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Our Awards and Recognition

Don’t just take our word for it

As pioneers in Australian five-star luxury and experiential travel, we have the accolades to prove our expertise. The Tailor and our Founder and Managing Director, Drew Kluska, have been recognised with prestigious awards, showcasing our dedication to crafting exceptional journeys across Australia.