Sydney 5-day Itinerary
Australia
Where to go and what to see in Sydney to get the most from your trip – a 5-day itinerary from destination expert and travel writer Mark Chipperfield.
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Overview >Bucket list experience:
Sailing & Boating on Sydney Harbour
Sydney, New South Wales, Australia
Credit Shutterstock.com/Kevin Hellon
Last updated: 09 November, 2022
Sydney’s harbour is considered by many to be the most beautiful in the world, so getting out and exploring on the water – be it by yacht, motorboat, jetboat or even sea kayak – is a must-do.
A range of boating options is available, from short sightseeing pleasure cruises, to days spent moored up (and swimming) off hidden sandy coves, to romantic sleepovers on board.
If you don’t fancy the cost or are not enamoured of boats, at least take the Manly ferry from Circular Quay and back for a similar, if less intimate, harbour experience. For a mere few dollars, it’s outstanding value.
Sail in a tall ship
For a more cultured (if touristy) twist, try a 2-hour sailing cruise aboard a vintage tall ship. It’s not as intimate, as you’ll be sharing the experience, but you’ll learn about Sydney’s maritime history and can help hoist the sails.
Spend the night on the water
EastSail offer an (expensive) opportunity to spend a romantic night on the harbour. The Overnight Indulgence package includes a private evening sail, a safe anchorage, dinner and breakfast. Your skipper will leave you overnight, return in the morning and sail back you to the marina. Choose from a yacht or motor cruiser.
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Destination Guide >Price from: £40
Minimum age: Any
Age suitable: 13+
When: All year around
Duration: -
Getting there & doing it
There are a number of pleasure cruise operators based at Darling Harbour, but these tend to be the touristy options (which are still fine). A better option though is to head to EastSail, based at the marina in the picturesque Rushcutters Bay, a 10-minute cab ride from the city or the Woollahra Sailing Club at the equally pretty Rose Bay, a further 5 minutes along the coast. If you want to try sailing, both offer a 2-hour ‘taster’ sailing lesson.
When to do it
Charter and sailing lessons are available all year round by private arrangement.
There’s never a bad time to be on the water, though July to October is best if you plan on swimming, otherwise the water is too cold.
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Our selection of the best Viator tours of this attraction or activity
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Beginner's Kayak Tour in Sydney - Gorgeous Aussie Beaches and Bays
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Our writer’s picks of the best places to stay near this experience, closest first
Wildlife Retreat At Taronga
Sydney, New South Wales, Australia[1.7 miles]
A luxurious wildlife retreat offering you the chance to spend the night with some of Australia’s most colourful critters, in the comfort of an elegant guest room.
Official star rating:
Ovolo Woolloomooloo
Sydney, New South Wales, Australia[1.9 miles]
A glamourous, stylish hotel in a restored heritage pier, that’s also now a buzzing wharf, with excellent restaurants. Conveniently located just 15 minutes’ walk from downtown.
Official star rating:
Spicers of Potts Point
Sydney, New South Wales, Australia[2 miles]
A character-filled boutique hotel set in three grand Victorian terrace houses. A convenient location for sightseeing, in one of Sydney’s nicest residential suburbs.
Official star rating:
Larmont Sydney
Sydney, New South Wales, Australia[2.4 miles]
A contemporary hotel with affordable rooms in the heart of trendy Kings Cross, close to the city centre and good transport links. An ideal base for sightseeing away from the crowds.
Official star rating:
Destination guides including or relevant to this experience
Sydney
New South Wales, Australia
One of the world’s most dynamic and glamorous cities, with golden beaches, world-class eating and dining and effervescent, friendly people.
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Overview >Our writer’s recommendations of other bucket list experiences our writer says you must do in this destination, closest first
Kayaking on Sydney Harbour
Sydney, New South Wales, Australia[1.6 miles]
See some of Sydney’s most famous landmarks – including the Opera House – from the water, with a kayak tour around the world’s most beautiful natural harbour.
Best for ages: 4+ | £70 | 2 hours
Taronga Zoo
Sydney, New South Wales, Australia[1.8 miles]
A world-class zoo overlooking the city and harbour – the ideal place to see your first kangaroo, koala or platypus.
Best for ages: 4+ | £25
Sydney Opera House to Royal Botanic Garden walk
Sydney, New South Wales, Australia[1.9 miles]
One of the world’s great scenic walks – a one- to two-hour, wildlife-filled stroll that takes in Sydney’s harbour, the Opera House, Mrs Macquarie’s Chair and the Royal Botanic Garden.
Best for ages: 4+ | Free | 1-2 hours
Sydney Opera House
Sydney, New South Wales, Australia[2.1 miles]
Magnetic, enchanting and still remarkably modern, this iconic Opera House is a must-see. Walk around the outside or book in for a guided tour or performance.
Best for ages: 13+ | Free
Other worthwhile experiences near this experience if you have time or interest..
Experience
Fort Denison
Sydney, New South Wales, Australia[1.1 miles]
Built during the Crimean War, this little historic gem sits in the middle of Sydney harbour. It’s now a museum, with fascinating exhibits like a canon gun powder store and a tidal gauge room. Daily ferries go from Circular Quay.
Best for ages: 6+ | £5
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Experience
Boy Charlton Pool
Sydney, New South Wales, Australia[1.6 miles]
Sydney is famed for its ocean and harbourside pools and this stunning harbourside pool is a stand-out. The Botanic Gardens are on one side, harbour views on the other. Great swim and sunbathing; there’s a fine cafe on site too.
Best for ages: 4+ | £12
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Experience
Justice and Police Museum
Sydney, New South Wales, Australia[2.4 miles]
This small museum, set in two former police courts and a former police station, was the original legal hub at the time of the settlers. Today it preserves the history of crime and punishment in the city, with exhibits on famous criminals, collections of weapons and restored prison cells.
Best for ages: 6+ | £7
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Vivid Sydney
Sydney, New South Wales, Australia[2.5 miles]
Vivid Sydney brings some of the world’s most creative minds and the latest digital light technology together to create astonishing installations that transform the city skyline and night sky.
Best for ages: 4+ | Free | 3 weeks
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