Call an Australian luxury travel designer at The Tailor on: +61 (0)8 8354 4405

Australian Hand-Crafted Journeys

Our Ultimate Sydney

BLOG | Securing its place as one of the best travel destinations in the world for 2024 according to readers of Conde Nast Traveller, Sydney is a staple on any Australian itinerary.

Boasting one-of-a-kind experiences, a stellar dining scene and some of Australia’s most luxe accommodations, we’ve put together a list of not-to-be-missed experiences for your next trip to the world’s most famous harbour-side city.

Whether it is private shopping complemented by VIP dining and sought-after encounters or travelling like a local and uncovering some of the city’s hidden gems, our expert Travel Designers are highly skilled in the art of making sure your travel is tailored to you, crafting unforgettable journeys and surprising and delighting our guests at every turn.

Make the most of your next trip to Sydney by including a few (or all) of the following during your next trip with The Tailor.

1. Paspaley Pearls: Private Showing

Paspaley Pearls

The name Paspaley has become synonymous with highly sought-after South Sea Pearls, which are harvested off the remote Kimberley Coast in the far north of Australia. The Paspaley family has been cultivating these beautiful pearls in Australia since the 1930s, and today are known for being the world’s most important producer of cultured pearls. Thanks to our special relationship with this great Australian company, The Tailor can arrange a special behind-the-scenes tour of the flagship Paspaley store in Sydney. Guests who take this tour will enjoy a private viewing of some of Paspaley’s most exclusive jewellery pieces, plus an insight into the delicate art of pearl cultivation.

2. Sail On Sydney Harbour

Local Eyes Harbour Tour

As one of the most famous harbours in the world, boasting views that go far beyond just that of the Harbour Bridge and Opera House, sailing on the Sydney Harbour is an unmissable bucket list item to include in your Sydney itinerary. Set sail aboard a luxury vessel to discover hidden beaches, see picturesque coastal gardens, marvel at grand harbourside homes and disembark to explore pockets of natural bushland. Dine on locally caught seafood with a glass in hand as the sights of the most beautiful natural harbours in the world pass you by.

3. Opera House: Private Tour

Guests being shown around the exterior of the Sydney Opera House by a guide

Undeniably one of the most iconic silhouettes in Australia, the Sydney Opera House is one of the most visited cultural sites in the country. Learn about the design, history and hidden secrets of the Opera House with a behind-the-scenes private tour of this architectural marvel. This bespoke tour also provides guests with the opportunity to visit areas of the building normally closed to the general public, such as the green room, the rehearsal spaces and storage areas. More than 50 years after its completion, the Opera House remains Sydney’s foremost venue for opera, theatre, ballet and other live performance.

4. Seaplane to Cottage Point

Cottage Point Inn

Situated deep in Ku-ring-gai Chase National Park on the tip of Sydney’s Northern Beaches, Cottage Point Inn is one of Australia’s most exclusive dining experiences. Under the direction of French chef Guillaume Zika this elegant waterfront eatery has created one of Sydney’s most dazzling menus, with fresh local produce taking centre-stage. Arriving at the restaurant via private seaplane with amazing views of Sydney Harbour and the northern beaches as your appetiser, this former general store and post office offers a European-meets-Australian-style dishes in one of Sydney’s most stunning dining spots.

5. Explore Sydney’s Art Scene

Sydney Art

Although Sydney is best known for its stellar culinary scene and natural beauty, the city also supports a thriving arts community. Apart from the two major public galleries, the Art Gallery of NSW and Museum of Contemporary Art, Sydney offers a large number of private galleries, specialist dealers and individual studios. A private guide can arrange introductions to some of Sydney’s most important curators, dealers and artists. These fully escorted tours can be designed to suit your particular interest as a collector – such as an individual artist, a particular era or medium.

6. New Year’s Eve Fireworks

New Year's Eve 2021, Sydney Harbour

A bucket-list experience for any traveller to Australia, there are fewer things more iconic than the New Years Eve fireworks display on Sydney Harbour. An amazing display of pyrotechnics, this event draws an estimated one million spectators to the harbour foreshore every year. Whether you want a berth at the Opera House, your own boat at the centre of the harbour or one of the most sought-after hotel rooms in Sydney for a front row seat to the mesmerising display of colour and light, let The Tailor create your perfect New Year’s Eve celebration.

7. Explore the Northern Beaches

Family walking the boardwalk between Bondi to Bronte Beach with beach and cliff-side housing in the background

Go beyond some of the city’s best-known shorelines and embark on a private tour to the northern side of Sydney. Explore hidden coves, local surf spots and pristine stretches of white sand beaches with a glass of bubbly in hand as you discover the lesser-known pockets of this iconic city. Experience Australia’s famous surf culture as you take part in a one-on-one surf lesson, snorkel under jetties and explore the unique marine life or hike along coast bush trails taking in the stunning coastal views while learning about the region’s flora and fauna.

8. Sydney BridgeClimb

A group of people climbing the Sydney Harbour Bridge with the Opera House in the background

A quintessential Sydney experience, the Sydney Harbour BridgeClimb acts as the perfect bookend to your city adventures. This journey combines a thrilling climb 440 feet (134 metres) above sea level with panoramic views of Sydney and its famous harbour. Led by knowledgeable guides, climbers are treated to captivating stories about the bridge’s history and Sydney’s culture. The perfect blend of excitement, scenic beauty, and cultural immersion.

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Australian Hand-Crafted Journeys

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