Recently voted “the world’s friendliest city” by the readers of Conde Nast Traveller magazine, Sydney is also in the running as Australia’s most glamorous city, thanks to its sparkling harbour, fantastic ocean beaches, stylish waterfront restaurants, vibrant bar scene, up-market shopping and, of course, iconic Opera House.

Ideally the first-time traveller should spend at least a week exploring the Harbour City, but since we know that this often not possible, The Tailor team has come up with a list of 10 must-do Sydney experiences for the visitor on tight schedule. As we all know the very best way to experience any city is with an experienced local guide – which is exactly what you can expect when you book with The Tailor. This Top 10 is not an exhaustive list – why not consider adding other unique experiences, such as sea kayaking on the Sydney Harbour, paddle boarding at Manly or cycling through the Northern Beaches? Our travel designers will be delighted to create the perfect itinerary just for you.

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1. Paspaley Pearls: Private Showing
The name Pasplaley has become synonymous with South Sea Pearls which are harvested off the remote Kimberley Coast in the far north of Australia. Indeed, the Paspaley family has been cultivating these beautiful pearls in Australia since the 1930s. Thanks to its 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.

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2. Sail On Sydney Harbour
Anyone who has seen images of the Sydney to Hobart yacht race or the build up to the city’s New Year’s celebrations will understand that the Sydney Harbour is a marvelous place for messing about on boats. Whether you want to skipper a maxi yacht or relax in style on a luxurious motor cruiser, The Tailor can find the perfect craft for your aquatic adventure. Imagine sailing past the Opera House, Sydney Harbour Bridge, Taronga Zoo and other famous landmarks? Or how about sleeping onboard for an even more memorable experience? Whatever your boating passion, let the team at The Tailor can make it happen on Sydney Harbour.

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3. Opera House: Private Tour 
Acknowledged as one of the greatest buildings of the 20th Century, the Sydney Opera House is now one of the most visited cultural sites in Australia. By booking a private tour of the Opera House, visitors learn about the design, history and hidden secrets of this futuristic building. 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 40 years after its completion the Opera House remains Sydney’s foremost venue for opera, theatre, ballet and other live performance.

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4. Sydney BridgeClimb
Before he became an actor Paul ‘Crocodile Dundee’ Hogan worked as a rigger on the Sydney Harbour Bridge. Thanks to BridgeClimb even people with no head for heights can enjoy the thrill of climbing to the top of its 141-metre high span. Known affectionately as ‘The Coathanger’, this beautiful bridge has played an important role in the history of Sydney. Apart from the sheer thrill of clambering across its famous span, climbers also learn about the bridge’s design, construction and some of the famous people, including Paul Hogan, associated with this famous Sydney landmark. Early morning and nighttime climbs available.

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5. Seafood Culinary Masterclass
Sydney is a city famous for its excellent seafood, so foodies will naturally want to visit the bustling Sydney Fish Markets. Why not take things up a couple of notches by booking a culinary masterclass with your own private chef? Your backstage experience starts on the market floor during the daily fish auction. Students then move to a professional kitchen overlooking the harbour and learn how to prepare a five-course degustation menu under the direction of a professional chef, with plenty of tasting along the way.

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6. Seaplane to Cottage Point
Buried deep in the Ku-ring-gai Chase National Park 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. What better way to arrive at this restaurant than by private seaplane? Guests enjoy stunning views of Sydney Harbour and northern beaches before touching down on the pristine waters of Cowan Creek.

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7. Explore Sydney’s Art Scene
Although Sydney is best known for its high quality dining 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.

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8. New Year’s Eve Fireworks
Ever wanted to see in the New Year before the rest of the planet? Then you need to book a front row seat overlooking Sydney Harbour for the annual firework display – an amazing display of pyrotechnics, which now draws an estimated one million spectators to the harbour foreshore. Whether you want a berth at the Opera House, your own boat on the harbour or one of the most sought-after hotel rooms in Sydney, let The Tailor create your perfect New Year’s Eve celebration.

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9. Blue Mountains Adventure
Just 50 kilometres (31 miles) inland from Sydney lie the Blue Mountains, a vast area of ranges, ravines, waterfalls, natural bush land and spectacular rock formations. The mountains are a mecca for all types of outdoor adventure, such as hiking, mountain biking and abseiling. Let us whisk you into this rugged wonderland by helicopter, flying over famous landmarks such as the Three Sisters and Wentworth Falls. Once on the ground, you’ll be met by an experienced guide who will take you on a private adventure in the mountains.

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10. Learn To Surf
Generations of young Australians have learned to surf on the breakers at Bondi Beach, so why not follow their lead and join a surfing class on this world-famous stretch of sand? The Tailor can arrange a one-on-one session with one of the surf school’s best instructors so you’re bound to catch a wave or two by the end of your lesson. This is great fun for people of all ages and swimming ability. Afterwards enjoy a relaxed lunch at Icebergs, an elegant dining room celebrated for its sunny, modern cuisine and amazing ocean views.

Bio pic of The Tailor

About The Tailor

Founded by Drew Kluska in 1998 on a platform of excellence and authenticity, The Tailor offers discerning travelers the opportunity to visit the Australia people only imagine in their dreams. In conjunction with hand-selected destinations and hosts, an entirely different personality of Australia is revealed. This is a side of Australia the majority of Australians do not even know exists. The Tailor has an enviable list of past travelers and was named by National Geographic as one of 2009's "Best Adventure Travel Companies On Earth." It has also been recognized by the 2008 Australian Gourmet Traveller Magazine Awards as the "Best Tourism Innovator" and as one of the "The top 50 travel experts you need to know worldwide" by the prestigious Conde Nast Traveller UK. The company has been featured in many other leading international publications such as Travel & Leisure USA, Elite Traveller USA and Vogue.
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