Rough Draft: 4 Day Itinerary for Sydney, Australia

Rough Draft: 4 Day Itinerary for Sydney, Australia

August 2020

Rough Draft: Sydney, Australia

Due to the COVID quarantine, I am creating rough draft, “off the shelf” travel itineraries for when travel resumes normal operations so we do not waste any time getting out and exploring!

Ever since we did our planning to New Zealand where I foolishly thought we could also include Australia as well in two weeks, I knew a separate trip would be warranted. It is a 5-6 hour flight from New Zealand to Australia – not exactly next door! Australia is enormous and there is so much of the country to explore that even a month trip dedicated would still miss things. My brother has had the opportunity to dabble in the eastern portion of the country and I am sold (was sold before to be fair!). I thought it would be really neat to road trip from Sydney to Melbourne (or vice versa) all up thee eastern coastline.

But in the event there is either an extended or abbreviated trip – since we have no idea what post-COVID travel will be like – I wanted to take time to focus on just the city of Sydney.

What is there to do?

Sydney has so many attractions but I think the most iconic photos of the city include the Opera House and the Harbour Bridge but do not just look at them, experience them!

  • Sydney Opera House is beautiful on the outside but don’t forget to take a peek inside. There are tours offered as well as the option to see a show.
  • A very popular thing to do is climb the Harbour Bridge so book ahead if you want to opportunity. It is not a cheap experience but there are different heights to choose from if you are not into heights or want a more budget friend option.
  • Don’t want to climb the bridge or do not want to spend that much money? Try the Observation Deck instead for a panoramic view.
  • Royal Botanical Gardens spans over 70 arces are offers many exhibits to explore and entrance to the grounds is free!

There are so many places around Sydney that make for a perfect half or full day trip.

  • Wine tasting in Hunter Valley Wine region – can rent a car and have a self guided, at your own pace experience or book with a company that will set everything up from Sydney
  • Hiking Blue Mountain – can rent a car or take a train to Katoomba for a transformation of scenery
  • Bondi Beach and Manly Beach – can rent a car or take public transit options or ferry to these locations, both of which are very popular and scenic

Where to eat?

There seems to be good food no matter where you go! It was hard to make final decisions on where to dine without being there so I made a chart after the itinerary highlighting the top recommendations I found while researching this trip. Of note, it seems to be all too easy to stumble into a very expense place, especially around the Harbour area – fancy tasting menus with a million dollar view. That being said, there are tons and tons of affordable and delicious options from what I can see.

For those day trips I intend on including in the trip, I picked a few of my favorite food finds to add to the itinerary.

Here is how I would spend exploring the city and surrounding areas!

Day 0Travel to Sydney
Day 1Morisset – Kangaroos
Wine Tour – Hunter Valley 
– Krinklewood 
– Oakvale Wine
– Scarborough Wine
– Lake’s Folly
– Hungerford Hill
– Harkham Wine
– Usher Tinkler Wines
– Hanging Tree Wines
– Iron Gate Estate
– Petersons Wine
– Briar Ridge Vineyard
Day 2Blue Mountains
– Three Sisters at Echo Point Lookout
– Katoomba Falls 
– Three Sisters to Katoomba Falls (3.1km)
– Gordon Falls
– Empress Falls
– Elysian Rock Lookout
– Bridal Veil Lookout
– Wentworth Falls (1.4km , 1 hour)
– Jamison Lookout
– Jenolan Caves
Day 3Sydney Opera House
Hardoud Bridge
Royal Botanical Gardens
Observation Deck
Sunset at Mrs. Macquaries Point
Day 4Coogee Beach to Bondi Beach Coastal Walk
Day 5Depart Sydney

For food around Sydney, here are just a few places that were highlighted while doing research planning this trip. It is impossible to find them all but figured this was not a bad place to start! If I missed any of your favorites or you have ones listed that are a hit or miss, let me know.


Nice Meal


Lotus Dumpling Bar

Mr Wong

White Rabbit

Harry’s Cafe de Wheels

Bodhi Restaurant

The Grounds of the City


Home Thai

Three Williams Cafe

Aira Restaurant


Cafe Sydney

Gelato Messina


N2 Extreme Gelato

Flour and Stone

Black Star Pastry   

Bourke Street Bakery


KOI Dessert Bar

If you have been to Sydney, let me know what I missed and what your favorites are!

We had the chance to test out this itinerary to Sydney in 2022!

Check out all the blog posts from our trip to Sydney here!

Don’t forget to check out all DESKRIB itineraries here!

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