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Sailing the high seas of Sydney Harbour was never really a thing that I wanted to do. There was no desire to get my sea shanty on. To ride the rolling waves and pay homage to the Sydney Opera House. When the opportunity arose to fly to Sydney and cruise with the Travel Massive Sydney crew there was no way I was going to let this adventure sail right on by.

This is a tale of my 24 hour whirlwind trip to Sydney in an attempt to play tourist. With thanks to Travel Massive for hosting me and the OzCat Luxury Cruise for taking care of this failed sailor.

Why bother going to Sydney?

As we have previously chatted about this summer is really about James and I getting about to exploring more of Australia. In my old life of corporate pencil skirts, black shirts and red lipstick I’ve spent a bit of time travelling up and down the east coast of Australia. Into airports, out to offices, do the work and then home again. Occasionally there was an over priced hotel and some shitty food included. This pretty much sums up my Sydney experience.

Into Sydney. Into office. Into hotel. Back home again. <- insert tired cranky Jean here ->

Not the best experience to have of a city. I’d found Sydney to be a clicky, over rated city that wasn’t particularly friendly towards young professional women.  I really did feel the need to explore Sydney and give this city a chance. I think that as a naturally born Melbournite I was predisposed to dislike Sydney.

It was time to give Sydney one last chance to impress me.

Time well spent as a tourist.

Firstly thanks to Ian from Travel Massive for playing host. It really was a lot of fun tramping around Sydney with someone who really knows the city. Our trip was meant to be with our flights arriving into Sydney Airport within 10 mins of one another. The train ride from the airport to Circular Quay flew by as we caught up. As friends do.

Than it was off to an afternoon of hard work at Manly. The ferry ride across took us around 30 mins and was rather pleasant.

We were hosted by another Travel Massive member in Manly. I’d heard a lot of good things about Manly and quickly feel in love with the area. I can see why so many people are renting here. There’s great beaches, excellent areas for dog walking, great coffee and some super cute houses.

Is the coffee better in Sydney or Melbourne?

Melbourne. Without a doubt coffee is better in Melbourne. Though I will say that there isn’t anything wrong with the coffee that I had in Manly and in Sydney. Generally speaking it’s pretty hard to stuff up a skinny latte. Sydney’s barista’s may have been a little more sulky then their Melbourne counterparts but that could also be due to the location of the cafes visited. I highly recommend the Roast Office in Manly.

Cruising around the Sydney Harbour.

The team at Ozcat certainly gave us a memorable experience on their latest vessel. The afternoon weather gods hadn’t played nicely with us and certainly felt the need to shower Sydney with mild torrential rain. Despite the few hours of miserable weather the Ozcat crew kept in contact with the organisers and assured us that all would be fine for the evening cruise. Sadly some people didn’t have faith in these well worn sailors and made the decision to not join in the frivolities. The evening started up with a few drinks at the Cargo Bar, then a pick up from the Wharf across the walk way. It was so easy to get from one to the other.

Now the fun thing about these wharf collections and drop off is the timing. There is super strict timing for vessels docking, collecting and moving on. No fussing about here. While waiting at the Cargo bar and sneaking in a glass or two of sparkling I did get to watch several party goers miss their boat departures. Seriously ladies your lipstick application wasn’t that important.

There’s a strict no shoes policy on board. So don’t forget to pedicure it up the night before. Once on board everything was taken care of for us. As the organisers had opted for a BYO catering, copious amounts of ice was thrown into the two eskies along with a wide variety of beverages and catering was prepared.

Throughout the evening the on board staff sneak around tidying up and ensuring that the space is kept as safe as possible for guests. As our cruise set off we sailed by the Opera House, the Sydney Harbour Bridge and a few other key monuments that I forgot to take note of. Eventually ending up in a small bay area and anchoring down for a while allow guests to go for a swim.

It really was an amazing way to explore the area and enjoy a little bit more tourist time in Sydney. The cruise route taken allowed me to see new areas of Sydney that I’d never seen before as well as enjoy some old favourites.

At the end of the evening we’re returned to our original departure point. Rushed off the boat, along with our shoes, to battle the Sydney streets and all the other end of year celebrations.

Getting to Sydney

Sydney is a really easy city to get to. Especially coming from Melbourne. The easiest and most affordable way, taking into consideration the value of your personal time, for such a short trip is to fly. On a good day the flight is just over an hour. Depending on poor weather it can be up to 90mins, with some time spent circling in the air. A side note- Sydney airport has a night curfew. So remember this is you’re planning on popping in.

I chose to fly with Jetstar as they offered the most affordable airfare of the budget airlines. Whilst flying with Qantas or Virgin would have been lovely the flights one way with these companies cost more then my Jetstar flight. Despite the intense competition on this short route it still isn’t terribly affordable. My flight cost in total was $162AU return, not including checked in luggage.

Need to book a flight? Find cheap flights here.

Travelling by train.

If you are going for a more slow travel then it’s easy to catch a train or bus from Melbourne to Sydney. The trip is from 10-12 hours depending on which service you take, weather conditions (in hot weather Australian trains get sleepy and go slower) and general life of public transport.

At the time of writing the cost for an economy train ticket Sydney-Melbourne is $131 AU. If you’re travelling from Melbourne you can use the V-Line system.

Overnight Bus?

Greyhound buses operate an overnight service, which departs from Melbourne’s Southern Cross train station. Buses depart at 8pm and take approx hours. At the time of writing the cost for a bus ticket Melbourne-Sydney started at $89 AU

Where to sleep in Sydney?

Sydney is a rather large city, ever expanding city. Unlike Melbourne there’s no specific one area to base yourself in that will give you great access to everything. Though if anyone knows of this area please let me know in the comments below. Being such a large business driven city there are a lot of hotels and hostels around. It can be really confusing.

According to our Sydney based friends Circular Quarry isn’t a bad place to base yourself. In all honesty Sydney has a fairly good public transport system. So it’s easy to get around town. The ferries take a  bit of getting used to but there are ample staff to point you in the right direction. Or worse case scenario Uber!

Wondering where to stay in Sydney?

Air BnB?

Rent is a killer in Sydney. Most people I spoke to are paying double or more then what we are paying in Melbourne. So it’s not unsual to find people supplementing their rental debt with Air BnB guests. A quick search on Air Bnb found rooms from $50 AU up to entire houses for $1500. So there’s a lot of options available for you.

If you’d like to try out Air BnB for the first time why not use this link and get yourself a $50 AU credit.

Final thoughts on Sydney…

Sydney certainly did a great job of changing my impression of the city on this trip. It really did make a difference being around like minded people and not just being there purely for work. As a city to visit it’s great as a tourist.  With so many historical buildings just everywhere it makes walking the streets of Sydney a visual pleasure. In certain areas.

Over all did I fall in love with Sydney? Not quite. I think we can classify our relationship as frienemies. I can’t push past the use of ferries to get around, the extraordinary rents charged and the general vibe of the city. The urban sprawl is happening exceptionally fast and the city is fastly loosing it’s cultural identity as it stretches beyond the boundaries. It’s not as cosmopolitan or as friendly as Melbourne.

Will I return? Of course. Somewhere along the line I’ll be there, beyond the international airport and enjoying a coffee or two with any of the wonderful friends I have living there.

So tell me. What’s your preference – Sydney or Melbourne?


  1. This is a really good read for me. Must admit that you are one of the best bloggers I have ever read. Thanks for posting this informative article.

  2. This is a really good read for me. Must admit that you are one of the best bloggers I have ever read. Thanks for posting this wonderful article.

  3. I’m visiting both Sydney and Melbourne in April. Do you have a blog on Melbourne?

  4. Helpful and nice to know your impressions about Sydney and, sometimes, compare it to Melbourne! Anyway I lived in Melbourne for 6 months and went to Sydney just 1 week for Holiday at the time of my staying in Australia! Let’s tell you my impression: I found Melbourne perfect to live, everything works efficiently and it’s possible to find a job easily, especially in the CBD; Amazing coffee culture (I am Italian .-D) and lovely LOCAL food. What about Sydney?!?! Well, perfect place for holiday, stunning beaches around it, weather is better than Melbourne and nothing bad to say about its art and architecture!
    I really don’t prefer one of those because there plenty of good things in both cities, anyway…. I MISS THEM!! Thanks for sharing, this post brings me back to Australia for 20 minutes! 😀

  5. I loved Sydney, but didn’t get the chance to go to Melbourne. After having been there three times, my other half point-blank refused to go again! I found the Sydney v. Melbourne rivalry hilarious 🙂 And Brisbane seemed to be a happy medium in between (or, as one Sydneysider said to me, “At least it’s not Melbourne…” !!)

  6. Australia is list and it is definitely tricky to choose between Melbourne and Sydney. The comparison you have provided on rent is gonna help us decide on our confusion when we visit. Thanks!

  7. Sydney isn’t popular for nothing. The view of the Sydney Harbour is just breathtaking. Haven’t been to Melbourne so I won’t be able to compare but I bet it’s just a matter of what kind of adventure you’re after!

  8. Good pointers and insights into how the 2 cities compare. We have plans to visit Sydney, but that has a lot to do with having friends who live there. We’d love to see the opera house on a harbour cruise.

  9. I’d love to visit someday. You coffee comparison comment is funny! I think there must be some decent place to get coffee in Sydney too!?!

    • Oh there certainly is

    • I live in Sydney and there are some great coffee places, but the general standard of coffee is definitely better in Melbourne.

  10. I’ve never been to either as I’ve never been to Australia, but I’d love to visit both. I think Sydney seems like a nice city to visit as a tourist. Cruising around the harbor looks like a lot of fun, I think 🙂 And I’d love to see the famous Opera house 🙂

  11. Maybe it was not a love at first sight, but after few more visits you could develop a real relationship with Sydney! I would love to take cruise and I’m still sad we did not take one in NYC. Taking pictures of the harbour and skyline is my favorite.

  12. I’ve never been to Australia so I don’t know if I’d like Sydney or Melbourne better. Sounds like Sydney’s a lovely place too and quite similar to Vancouver (where I’m from). I know many people who have moved to Sydney for work from Vancouver and they love it there!!

  13. I prefer Melbourne too. Sydney is quite cosmopolitan compared to Melbourne and maybe that is why. I did go jet sking around the Sydney harbour but never took a cruise. But I did my first and only skydiver here and that is what made my Sydney experience memorable.

  14. We don’t have a preference yet because we’ve never been to Australia! But your comments push us towards Melbourne 🙂 That’s great that you finally had a positive experience in Sydney though, it seems like a city that has its charms too. Maybe the rivalry between Melbourne and Sydney is like L.A. and New York! (we’re from LA 🙂 )


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Just a little FYI- this article was written in partnership with me and me! Any and all views and opinions expressed are entirely my own based on personal experiences when travelling and are honest and factual without any bias. There are affiliate links in this post. Which should you choose to purchase via these links I get a very minimal percentage which may help buy me a coffee on the road.



Founder, Principal Blogger & Coffee Drinker

Coffee Lover | Travel Blogger | Horse Rider | Adventure Racer | Donut Dame. Generally nice lady-enjoys wine, indie movies & random dance parties in my tent.

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