“The only return flight we have involves a long overnight connection in Sydney, do you want us to book you a hostel?”

My first thought was “what kind of night am I going to have in a hostel that I’ll be checked in and out of in under 6 hours?”.

After my week in Fiji there would be no direct flights back to Melbourne, and my travel agent understandably saw it as a chance to sell one last add-on to a trip that was already blowing through my budget.

“I’ll have to have a think about it” I told him, even though I’d already decided to follow my second thought… what’s the worst that could happen if I left my bags in an airport locker and just wandered around Sydney all night?

I admit it felt like a crazy plan, so crazy that I was embarassed to let on to the travel agent that I was even considering it, let alone that I was actually going to do it.

Any traveller who’s taken in this part of the world will know that Sydney is it’s main hub, with its famous beaches packed throughout long, hot Australian summers and plenty of activity to take in during the day including some of the Eastern hemisphere’s slickest looking bars, as well as being blessed with the infrastructure to host festivals and other events under one of the most iconic skylines in the world.

But overnight, without a hostel and 10 hours to kill, with all the friends that I could realistically rely on for a spare bed still back in Melbourne? Landing there at 8pm and my flight to Melbourne not til 6am, this is the situation I’d put myself in.

But I was excited. Even though I had been to Sydney twice before, in April 2016 and again November 2018, I hadn’t had the chance to walk around Sydney harbour in 3 and a half years and thought the quick stop would be a fun chance to re-live the experiences of my previous trips there and hang around some places that would bring back a few happy memories.

 

I eventually had to give up on getting the perfect picture because the relentless rain won over – Sydney gets some serious downpours.

From the airport, a return train to Sydney Central cost about $35 and dropped me off half an hour’s walk from Sydney harbour. Making my way through the Central Business District (CBD) past Sydney’s historic buildings and glistening modern flagship stores, I noticed a few off-licences selling some last minute supplies to those getting ready for their nights out. The blaring shop lights illuminating a rich selection of snacks triggering a flashback of one of my first nights in Sydney where, in a mad scramble to prepare for pre-drinks, I arrived back to my hostel instead with a big bag of Doritos and salsa. I don’t know what my roommates made of it but I can’t imagine they’d have been too impressed.

The walk down to the harbour was longer than expected but led me to a much more peaceful setting, a Sydney harbour lit dimly by the moody lights of the surrounding skyscrapers and feeling very much like the focus point of one of the world’s great cities. I was able to explore two of Australia’s most loved landmarks with few obstacles and, as there were no big events on, had the time and space to take as many pictures as I wanted… I was surprised at how peaceful it was and I could have walked right into the opera house with no questions asked if I’d decided to.

In my many attempts to get the perfect, uninterrupted picture I ignored the growing downpour, hoping that a gopro that doesn’t take great pictures in dark and rainy conditions would somehow take some great pictures in these dark and rainy conditions. I eventually had to give up on getting the perfect picture because the relentless rain won over – Sydney gets some serious downpours, the horrifying amounts of rain the city is prone to was something I always remembered from my first 2 trips there.

 

In fact, the Sydney rain was partly responsible for me missing a 7am coach to a Blue Mountains day tour 2 years previously. I say partly responsible, though staying out til the early hours also played a role. A groggy weave through early-rising yuppies on an utterly soaked Kent Street without the guy who was meant to be getting the coach with me (he’d slept through his alarm so at least I made it further than him) was enough for me to say “not today” and head back to the shelter of the hostel, and probably more Doritos. We took the tour the next day but it wasn’t for lack of partying that night either.

With the rain hammering down I couldn’t help crack a smile at the thought that when morning arrived, it was likely that some other poor backpacker would be in the same position I found myself in that day, fighting their hangover to explain to a tour company why they should be able to rearrange the day trip they’d spent a mini-fortune on.

Anyway, I actually regretted not arriving at the CBD slightly earlier this time. If you want to watch the sunset in Sydney, there are some unforgettable pictures to be taken from Mrs Macquarie’s Chair close to the Botanical Gardens, about 15-20 minutes walk around the corner from the Opera House. Named after the wife of a 19th century New South Wales governor who apparently used to watch for ships from here, this is mostly the famous view of the city you see in pictures due to the fact that you can comfortably squeeze the Opera House and Harbour Bridge into one frame.

A year earlier on my second visit here, in these same gardens me and a friend had been lucky enough to watch DJs like MK and Green Velvet soundtracking the Sydney sunset at the appropriately named (and brilliant) Harbourlife festival, the best backdrop to a festival I think I’ll ever experience.

I found the walk from the Opera House a bit more hassle this time though, as the Gardens are closed at night and you have to follow different roads to get to Mrs Macquarie’s Chair. I gave it a go though. The detour taking me through Sydney’s leafy back streets and on a fruitless search for a gap in the motorway which would have freed up the route. I suppose I could have been wandering lost in a worse place than the centre of this great city.

However, Sydney Harbour isn’t the only place where you can gaze at the city lights. In fact it isn’t even the only harbour where you can do so. Since I had plenty of time to spare I made the 3km walk to Darling Harbour, where in the daytime I could have counted the local Sea Life and Madame Tussauds among my options, as well as the Harbourside shopping centre. I’d always felt a connection with this place after my first visit, walking down here hungover in search of free wifi and sitting in Starbucks with a coffee watching the boats for hours. At night the indoor options may seem like they are limited to bars but look under the surface and you’d be surprised. A walk around the harbour and over the heritage listed Pyrmont Bridge between Sydney CBD and the inner suburb of Pyrmont can be done at any time, and here was where I headed. The bridge runs across Darling Harbour’s Cockle Bay, and turning back halfway across while walking over from the CBD side I was greeted with another memorable cityscape, and probably one of the best views of the city outside of Sydney harbour. Nighttime in central Sydney has some great walks, and you don’t really have to look hard to find them.

 

Feeling that I’d maximised my opportunity to sightsee for the evening and not wanting to put myself in a position where I could miss my flight, I called it a night and walked back, this time in heavy rain, to the station to catch a train back to the airport. Despite being soaking wet I was proud of myself for making it back in good time. I’d been organised enough to find my way to the domestic terminal and with my flight to Melbourne not til 6, it should have been as simple as just collecting my bags and doing a bit of shopping beforehand, and maybe having a drink in the airport lounge to round off the night.

This pride was misplaced, however, as there were two problems: Firstly, Sydney Kingsford Smith is one of the only airports I’ve ever used that closes overnight. There was no getting indoors to shelter from the rain, let alone shopping or pre-flight drinks. I was pointed towards the McDonalds just outside the airport by a bus driver who I was lucky to even bump into considering the airport grounds were deserted, and made my way there to eat the rest of the night away with every other person who’d had the same misguided idea as me.

Secondly, Sydney to Melbourne is a domestic flight. So although I myself was in the right place, it was no good being in there if the bags I’d locked away after coming in from Fiji on an international flight were in a totally different terminal. Suddenly a relaxed end to the night turned into a mad rush between two ends of the airport that were inaccessible by foot and more than 10 minutes away from each other by train. So despite arriving early in a near-empty airport I still almost managed to mess things up, and not surprisingly ended up as that person I really didn’t want to be, the one who boards last.

But these are the kind of experiences only travel can give you and I’d do it all again given the chance. My main feeling wandering mostly aimlessly around the streets of Sydney was one of nostalgia for the great times I’d had there previously. If it was my first time would I have felt so happy trying to find my way around in the rain? Probably not. But with every turn bringing back memories of wild nights, day trips and old travel friends who had long since moved back home, it felt like I’d lived through it all again on this lonesome night. There was undoubtedly a bittersweet feel to it, one of a party that had long ago peaked and begun clearing out. A party you wished could go on forever. The one thing keeping me going was the thought that somewhere in that sprawling stretch of bustling streets, other people like me were having their own parties that they’d look back on one day with the same love.