The Ultimate Sydney Itinerary

Sydney is the capital of New South Wales, and one of the main entry points when coming to Australia. Our ultimate Sydney itinerary will help guide you through the streets of Sydney.  If this is your first visit to our fair country check our Australia travel tips for a comprehensive guide of all you need to know.

Whilst this Ultimate Sydney Itinerary, focusses on staying 3 days, highlighting some of the options you can choose from during your time in Sydney. Whether you just passing through, on your way to another state. Coming into town for a show, festival or looking for luxury Sydney escapes, we can show you around. We always recommend staying longer travelling slowwer, which is why within our ultimate Sydney itinerary there are enough options to add an extra day or 3 to it.

Within this ultimate Sydney itinerary, we cover how to get around, some of the best places to stay, eat & play. We have also included our favourite places to go & options for where to go if you wish to extend your time in Sydney.

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Preview – Ultimate 3-Day Luxury Sydney Itinerary

Our preview, briefly highlights what is possible for you to discover in your 3 days, with our ultimate Sydney itinerary…Our 6 steps to create the perfect itinerary, will help you further refine and add any personal touches you wish, for further luxury escapes in Sydney.

5. Day-1 – highlight activities & alternative options for your first day.
6. Day-2 – highlight activities & alternative options for your second day.
7. Day-3 – highlight activities & alternative options for your third day.
8. Where to Now – options for where to continue on your journey (if staying more than a weekend in Sydney).

Our pre-travel checklists, are the first step to start your independent travelling. Letting you relax and enjoy your ultimate Sydney itinerary know, everything’s been ticked off the list.

Checklists for:

• Before you travel
• organising travel essentials
• when to start dreaming and booking
• right up to the day before and walking out the door

History

Sydney was the the first city found & settled in Australia (1788), when the first fleet arrived from England. With the majority of residents being convicts, with sailors and marines as guards. Cadman’s Cottage, is one of the oldest surviving buildings in Sydney. Originally built as a coxswains barracks in 1815-16, it has seen many uses over the years and is now a historic site overseered by NSW National Parks and Wildlife Service.

To immerse yourself in the history of Sydney, both good and bad of colonists and indigenous people. A walk around Circular Quay, The Rocks area and Bangaroo reserve is highly recommended in your ultimate Sydney itinerary. You can choose to take a guided walking tour, immersing yourself in the past. Alternatively, if you are feeling adventurous wander the streets on a self guided tour starting at Circular Quay. Be sure to stop at one of the old pubs a great inclusion to an ultimate Sydney itinerary, or few underground bars are now open and on offer. In addition to some fine dining and accommodation set amongst historical buildings.

Other historical buildings can be found along Macquarie Street, these include Hyde Park Barracks, The Mint, Museums of History NSW, NSW Parliment House and The State Library. Just past the state library is one of the top entry points to the Royal Botanic Gardens, Sydney, which is well worth a wander. The gardens were established in 1816, and is a delight to wander about visit some of the extensive exhibits, wander down to the iconic Lady Macquaries Chair or have a picnic on the lawn, which in my opinion has some of the best views across Sydney harbour. 

Getting to & around Sydney

When travelling to Sydney from overseas or domestically, via airplane, you enter at Kingsford Smith Airport. Located 8km (5 miles) from the heart of Sydney. If travelling into the city taxi’s and private cars are available for transfers. There is also a train terminal available with direct access to the CBD. If staying in the city, this is often the option we take dependent on time of day.

For those arriving via rail from another state, you will arrive at the heritage listed Sydney Central Railway Station, which is located in the heart of Sydney City. The Central Railway Station is connected to the city circle line of the CBD, light rail, taxi’s and private vehicle transfer can also be arranged from the station. Central Railways Station is also one of the main terminals for inter-state travel throughout Australia via train.

Due to congested traffic, we always opt to walk around the CBD. However, if travelling distances or around the harbour the options include ferry, main and light rail train systems to get around the CBD. As Sydney has one of the most beautiful harbours in the world (my opinion), a day out on the harbour seeing it’s icons is a wonderful way to get around and a must for the ultimate Sydney itinerary.

Note: If you are driving into the city, we recommend planning your trip to include parking fees. Check parking fees at you accommodation and near by parking stations.

When to Go

Seasons

Whilst seasons are the same for all of Australia, no matter how well you plan your prefect Sydney itinerary you can be met with inclement weather. Below are the mean temperature, rainfall, sunlight & wind gust per months for Sydney. Other town specific weather information can be found at the Bureau of Meteorology (BOM). 

Note: These are only mean values and can vary over time.

Mean Sydney Climate (Source: BOM – 31 Mar, 21)

Festivals

Another factor that may influence your ultimate Sydney itinerary and when you are going. Can include a special event, whether it’s the Opera or a show. Alternatively, you may wish to include one of the special events or festivals that are one throughout the year in Sydney.

One of these events is Vivid where Sydney lights up the city with 3D light projections and amazing art installations. Bringing life to the city for the beginning of winter, Sydney Vivid Festival is definitely one to add to your ultimate Sydney itinerary.

Where to Stay

There are so many opulent accommodation options for your ultimate Sydney itinerary, it is exceedingly difficult to choose. That said, if you belong to one of the membership programs such as Hilton Honor, ALL – Accor Live Limitless, IHG or similar. We always recommend looking what your memberships offer first. That way you are able to take full advantage of your chosen rewards programs, collecting points along the way.

Alternatively, Booking.com, or Hotels.com are a great options allowing you to add filters for many preferences, hotel ratings and luxury level (4-5 Star Hotel) are just two options. Whilst we recommend looking to see the hotels your preferred group has to offer, first. These two booking sites also have their own programs that we recommend you join if you use regularly.

Alternatively, choose from the selection of hotels we have either stayed at or reviewed as the best luxury accommodations and restaurants in Sydney city. 

3-Day Luxury Sydney Itinerary

On the first day of any itinerary, if nothing has been pre-booked we always like to wander and take in the sights both known and unknown. No ultimate Sydney itinerary would be complete without a trip around the Harbour to view its icons.

We do recommend for any activities that are at the top of your list as a “must do” you book as early as possible to avoid disappointment. Be warned even in this ultimate Sydney Itinerary, we walk a lot, usually to compensate for all the delicious food we eat.

Having one of the delectable high teas around town is a must, or maybe that’s just me a self confessed high tea addict.

Note: As with any of our itineraries, days and activities can be mixed around, to suit your agenda and any bookings.

Day – 1

The first day of any Sydney escape, for me is a about visiting some old favourites.

• a wander through the Royal Botanic Gardens, this large expanse of green within the CBD of Sydney, is a breathe of fresh air and a delightful place to picnic
• whilst you can take one of the tours on offer, we like to self guide with the map. Note: The Gardens is 27 hectares (66 acres) in total with several steps.
• walking through the gardens to Lady Macquarie’s Chair, where in my opinion is the best views and photo opportunities of both the Opera House and the Harbour Bridge.
• crossing through the gardens to the Opera House, where you can take a VIP tour, Opera ticket & dinner.
• alternatively, we will visit circular quay and take one of the cruises about the harbour (some offer tours including lunch or dinner)
• we then return to our accommodation, and choose from one of the delicious restaurants for dinner.

Day-2

Day 2 of our ultimate Sydney itinerary, see us venturing out again after a leisurely breakfast.

• The Rocks area is full of history, for both first white settlement and indigenous dreaming stories (Note: Saturday and Sundays we recommend a trip to the Rocks Markets, where stalls feature local artists)
• wandering the streets of the Rocks area, you will discover some of the oldest streets and buildings of the first settlement of Sydney Harbour
• walk or catch a ferry to Darling Harbour, getting off at Barangaroo where you can take the Wulugul Walk along the foreshore, and visit the Barangaroo reserve, be sure to return to one of the amazing eateries for a light snack or lunch
• Darling Harbour is also home to the Maritime Museum, Madame Tussauds Sydney and the Chinese Garden of Friendship
• Combine the two with a personalised tour of the Rocks & Darling Harbour.

Both these areas are large enough, with diverse activities to keep everyone occupied for the day, before choosing where to dine. Alternatively, we can highly recommend a steak sandwich from Sydney’s oldest pub the Fortune of War, in The Rocks. The food and history within was delightful.

 Alternate Day-2

An alternative to day twos activities, if weather is accommodating would be a coastal walk. Taking in some of the best of Sydney’s Eastern Suburb beaches and the exceptional views they offer, tops off the ultimate Sydney itinerary. If travelling late Oct-Nov this is a great time to do the walk as you can view the Sculptures by Sea exhibit.

Some of the features include:

• the iconic Bondi Beach and baths, get a great view of the beach & baths the Beach Lookout
• Mackenzies Point offers more spectacular views, with the Aboriginal Rock engravings close by
• the views continue as you walk around to Tamarama Point & Bronte beach/baths
• a wander around the cemetry which was est. in 1877  taking in the views from the lookout
• continue along the path towards Coogee Beach & Sth Coogee Stairs that offer a great view of Wedding Cake Island

If you are feeling energetic, you can continue on to Maroubra. Make a day of it and stop off at any of the cafes or a pub for lunch along the way. The return trip can always be done by walking or there are plenty of cabs or cars on offer. You can even organise to have a car drop you off and pick you up at designated points at any time.

The walk is mapped by Google at 7.3km taking 1hr 33mins. However, stopping to take photos of the gorgeous views and for lunch along the way could easily make this 3-4hrs.

Graded as a Level 2 walking track. Suitable for most ages and fitness levels with occasional steep sections of stairs. Not suitable for prams or wheelchair users. Dogs are allowed if on a lead, and you can find drinking fountains available to refill or drink from at all the beaches.

Day-3

For the last day of this ultimate Sydney itinerary, after breakfast, we recommend a day on the harbour.

• wander to circular quay or one of the wharfs around Darling harbour to hop on a ferry and explore Sydney Harbour.
• visit Cockatoo island one of the 11 properties that make up the Australian Convict Sites World Heritage Property, inscribed on the UNESCO World Heritage List on 31 July 2010, visit the remains of the old convict area. Originally established for re-offending convicts from Norfolk Island. A fascinating place to visit, you can also stay in one of the heritage buildings that still remain on the island.
• a trip across the harbour to Manly is always a great way to get out on the harbour, wander the pristine beaches, visit one of the old pubs or delicious restaurant.
• alternatively, visit the Q Station, which was the quarantine station for incoming boats and passengers in the 1800’s through to the early 1980’s.
• a shuttle bus is available from Manly wharf, so you can take a tour, eat at one of the restaurants or wander about North Head for a different perspective of the harbour. (Note: Accommodation packages are available to stay at the Q Station in one of the heritage buildings)

Alternatively, if a day on the harbour is not for you…

• a wander along Macquarie Street, where several historically significant buildings can be found.
  • Hyde Park Barracks another of the Australian Convict Sites World Heritage Property, originally used to house convicts, the barracks has seen many uses over the years take a tour and discover them all
  • across from the barracks is Hyde Park a refreshing space of green within the CBD
  • St Mary’s Cathedral is also at this end of town and a delight to witness the stained glass windows throughout
  • the Mint, the oldest serving public building in the CBD, once known as the “rum hospital”
  • NSW Parliment House, conducts tours for the public when open
  • the State  Library has several collections and exhibitions

I hope any or all of these options entice you into one of these ultimate Sydney escapes, remembering that private guides and tours can be arranged for any or all of these options.

Extra Places for Day Trips 

Whilst your 3-day ultimate Sydney itinerary is at an end, if you have a taste for more and have some extra days. The next selection of options are all day trips that highlight the surrounds, north, south and west of Sydney. These are all available with a departures from Sydney, with many of them small group tours, which have many unseen benefits.

Alternatively, you can hire a car and explore any one of these areas independently. These points of interest are also a great start to exploring further a field. Using them as a start to an extended adventure visitng the best places in NSW and beyond.

To the South

Whilst Bondi Beach is another icon of Sydney, having grown up in the southern suburbs of Cronulla. I do have a somewhat biased opinion of the beach and surrounds. Exploring the Royal National Park has always felt magical, with its beautiful yet rugged landscape. From walks to waterfalls lagoons and cliff tops, if you are lucky some hang gliders will be out soaring over the ocean.  This is truly a delightful way to add to a luxury sydney itinerary.

Venturing further south brings you to the small town of Kiama, with it’s iconic blowhole and shop lined streets. Before heading to the Southern Highlands where you will be able to see the spectacluar Fitzroy Falls. Glide over the treetops on the zipline at Illawarra Flyway, before enjoying some of the local wine and produce in one of the heritage towns of the Southern Highlands. If extending you luxury Sydney itinerary consider the towns of Berry, Berimma and Sutton Forest as great stops overnight.

If you are up for a longer day and have a desire to visit Australias capital, a small group tour is available. This tour takes you on the 3 hr drive to the capital, stopping for morning tea before visiting the National Museum and the Australian War Memorial. A dedication to all Australian that have lost there life in past wars. If you are lucky enough to be traveling in September to October, you can visit Floriade, where spring is celebrated with abandon. From bulbs, and annual transforming the area into a canvas of colour. Held at Lake Burly Griffin, along with a spectacular hot air ballon display, it truly is impressive.

To the North

Whilst we currently reside in Tasmania (another luxury destination to come explore, filled with food, wine, whisky, spirits and the scenery…to die for). I did spend many of my adult years on the Central Coast and still visit family there regularly.

So what to do just north of Sydney…as you can imagine the beaches are some of the most beautiful and cleanest in the world (I may be bias). A drive along the coast to visit some of the northern beaches is definitely worth a visit. Whilst up north include Kuring-gai National Park in your day. Once more you are surrounded by beautiful bushland, for exploring.

Be sure to take the Red Hands Caves Walking track. Here you will just one of the important indigenous sites of the area, a strong reminder of the physical and spiritual connection our indigenous people have to the surrounding land.  Other sites can be found that hold great significance along the heritage walk at Kuring-gai National park.

If you’d like to go even further north and visit the Hunter Valley, try some delicious wine, spirits, cheese. It honestly is a food lovers paradise, and a great way to extend your ultimate Sydney itinerary. That said, there is so much to do and see around the Hunter Region that a whole new itinerary is needed for a weekend or long weekend getaway. As many events are held, in the Hunter Valley wine country its also prudent to see what’s on offer. A visit to the Hunter Valley Gardens is always a delight and the accommodation is fantastic..

& going West

An alternative conclusion to your ultimate Sydney itinerary is a day trip up into the Mountains. The Blue Mountains to be precise, which is part of the Greater Blue Mountains Area a UNESCO site. Learn how they got their name, ok I’ll tell you here…

It’s due to the oils from the distinct eucalypt trees in the area combining with dust particles and water vapour. Which is visible as as a blue colour due to the scattering short wavelength rays created when the sun hits the combined particles. Another significant indigenous cultural and spiritual site, learn how the three sisters were created and named. Visit the delightful town of Leura that is reminiscent of an era of the past, delightful cafe’s and a delicious chocolate shop are a must to visit.

Then travel a further hour west to the Jenolan caves, these belong to Australia’s largest cave system. In fact it is reported to be the largest cave system in the world. The discovery of the caves by first settlers, goes back to the early 1800’s. Though for thousands of years before, it was known by the Burra Burra people, a clan group of the Gundugurra Nation, who’s land the caves are on as Binoomea, “Dark places”.

There are 11 show caves to explore, with potential for more to be discovered. Indeed this is another of those places that deserves a weekend away, stay at one of the accommodation options at the caves, enjoy the café or restaurant during a day trip or experience discovering the delights of the area on a longer stay. Exploring all the wonders the caves has to offer, is truly something that should be done at least once.

Any or all of these extras to your ultimate Sydney itinerary, can be done with small group tours or independently. Hiring a car and venture beyond the capital to discover the delights on offer in NSW, Australia.

What about the East you may ask??

Well there is the Pacific Ocean and New Zealand, though that would be another itinarary altogether for another time…

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I am always happy to reply to any comments, suggestions for next articles or a hello. You can contact me through our Social Media or at jeanine@letsgoawandering.com with any questions or comments.