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  • Writer's pictureBillie Proffitt

What. A. Basic. Fuckwit.


6A arrival Sunday the 5th, I think? Until Wed the 8th...

Honestly, the Airport Train to the CBD is your best best for both cost & time efficiency - by the time you clear customs (y’all both have e-visas & e-passports, yeah?) & get your luggage, traffic will be icky in a cab. If you tell me which address you’re staying at, I’ll tell you your best stop/route. Honestly, just grab an Opal card (like Oyster in London, or kind of like Metro in NYC) & load it with like $45 - that should sort you for the 4 days you’re in Syds: Aiport rountrip is like AU$30. You can tap the card for funds on the trains, ferries & buses. Download the app “TripView” for maps/trips/navigating- they even recently combined Syds & Melbs into 1 app! (Used to have to download separate ones for different cities.)

The Hunter Valley (Pokolbin, NSW) for wine tasting - but it would be like flying into LA from across the globe & renting a car to drive to Los Olives for wine tasting... might be more trouble/time-consuming than it’s worth. Even if itis amazing!

ANYWHERE, literally almost ANY little cafe in Australia is going to have the most phenomenal coffees compared to America.

CAC - The Cruising Yacht Club of Australia

At Rushcutter’s Bay, it’s a great walk from the CBD *(the Central Business District - like how we say “Downtown”) if you have it in you, the closest train station is Edgecliff on the Orange Line heading toward Bondi Junction (the name of the Westfield Mall closest to Bondi Beach - the place most people think of when “Australia” is mentioned).

Sign in as a visitor in the book inside the sliding glass doors at the front - you’ll have to give your ID’s (because you live outside 15 km’s - club rules in Australia is that you get to visit without having a membership).

Lunch is great here! It’s the start of the Sydney to Hobart Yacht Race AKA: “The Rolex”, or “The Everest of Sailing”.

Gerard is a kind but ornery older man usually running the front & his daughter is the one who married an American man & lives in Glendale with her kids as I mentioned!

1 New Beach Road

Darling Point, NSW


Beach Days

Bondi Beach is the most famous & is like a miniature SaMo - like I said, stay in the flags & listen to the lifeguards while swimming. Also, grab a beer if you can at the Bondi North RSL - you’ll find “RSL’s” everywhere in Oz, they stand for “Retired Servicemen’s League” & are like way cooler versions of the Lion’s Club spaces here, fully staffed of course & liquor license possessing.

Cronella is in The Shire, probably not worth the trip, but there are less tourist crowds there & cleaner, prettier beaches. However, you’re going in autumn, so I’m not sure how many beach days (weather-wise) you’ll actually get... Probably be about 70’sF & the winds can be gnarly.

Hikes - the best hikes are in The Blue Mountains, but again, this is an entire day trip commitment. Not sure it’s worth it on this trip for you.

The Bridge Climb - super touristy, but I won’t even lie, it’s fun! Not much of a rush as it’s so safe, but beautiful nonetheless, plus helps you get your bearings about you.

The Rocks - farmer’s markets & street food & soooo much history! This is the START of the British colony. Also here is the Museum of Contemporary Art Australia. The train station is also the main ferry area for the CBD: Circular Quay (pronounced “key” - don’ want you to look all Yankee on my watch).

The Art Gallery of NSW - can’t miss it!

Also here is the Botanical Gardens & the walk to Mrs. Macquarie’s Chair, oh! And if you guys want a workout, there is a wonderful pool here I used to swim 30 laps a day here when I was training/the days I was in Sydney in the saline/chlorine mix) for only like $5/day. It’s called Boy Charleston Pool - not the one in Manly, just to clarify. Different part of the city, same pool name. Like their airports, LOL. It’s just gorgeous! And across from Thales/Navy in Woolloomooloo. Also close to Woolloomooloo Wharf with such good restaurants & a W Hotel I believe? Supposedly Russell Crowe lives at the end of it... oooooo! And Harry’s Cafe de Wheels on Cowper Wharf Road in Woolloomooloo. A necessary, super tasty (somewhat) evil - also perfect for super-shitfaced late-night grub. Actually, come to think of it, I think that's what it's meant for? Hahahaha...

The Manly Ferry to Manly - this will show you the Northern Beaches as it crosses like 1/2 of Sydney Harbour & will get you out to see the open Pacific almost facing home! Hahaha...

King’s Cross

All kinds of tomfoolery. The history here is intense & you’ll start to see why... Also, be aware, whoring is legal in Australia, you might happen across red light districts, it just is what it is. It’s all quite safe though, Love, regulated & all.

Nanda/Hobbs Gallery

Ask for Ralph Hobbs, I used to work for him writing, editing, creating stories in Hobbsy’s & his best friend’s books. :D Also helped cultivate a number of his artists’ careers.

“The Inner West”

Newtown/Glebe/Enmore/Earskinville/Ultimo - like I said these have the feelings of Silverlake or Echo Park: hipster & grungy & kind of DTLA-ish these days (without the tall buildings, more like East DTLA).

Check The Enmore Theatre listings & see if there are any good concerts on! I’ve seen some incredible shows there, plus the theatre is pretty intimate & beautiful old Art Deco.

And while you’re on that side of town, check out LDF Tattoo

Ask if Leslie Rice, my beloved & trusted friend is around. He’s done all 3 of my tats - funny story.

Marty, as I introduced you to - started the Small Bar Association in Sydney: They own Grasshopper (in the alley), Magazin, Supper Club, & some others...

Hyde Park

Quay Bar at Customs House has a great view - so does Opera Bar near The Sydney Opera House. Oh! You may want to check for concert tickets here too! Quite touristy, but hey, it doesn’t take away from the sheer magnificence & splendour!

Rockpool Bar & Grille

I love the building on Hunter Street & as I mentioned & the food is amazing. This is literally my favorite restaurant in Australia. <3

Frankie’s Pizza - ask for Chops, he’s my lovely Canadian friend who set me up on one of the most awkward blind/double dates of my life... the guy turned out to be friends with my estranged DeFacto spouse in Brisbane while I gave my now ex a “free pass” year to sort his shit out. LOLLLLL That shocked all 4 of us & made the rest of dinner a little tense. That guy was in liquor sales too! Hahaha! Truth is always stranger than fiction...


For the shops/style for your roommate. It’s swanky-chic & very fashionable.

Surry Hills is like the West Hollywood of Sydney: Crown Street is the most famous for good eats, cool shops & general everyday coolness. Kind of like Abbott Kinney these days.

Also Redfern - Jason Mowen’s store is here: but I’m not sure if he’s in Italy or Australia right now.

The Pitt Street Mall is the main Westfield in town, on Town Hall Station, a big one, learn it, know it. LOL It goes everywhere you want to via train.

Get the Banoffee Pie at Fratelli Fresh!

Actually anything at Fratelli Fresh, but don’t miss the Banoffee Pie! There are like 6 locations, Bridge Street is cool, but I think your roommate will love the one near The Grounds at Alexandria better.

King Punch - be aware of both fights & the “Lockout” rules for bar/“pub”/nightlife hours, however you won’t be in Syds on any weekend nights, so it probably won’t matter. Marty O’Sullivan will direct you for best watering holes.

My old apartment:

The Connaught

185 Liverpool Street

Sydney, NSW


My old studio: (doesn’t exist anymore because of the new train line)

129A Wellington Street

Waterloo, NSW


My other old terrace house:

12 Crown Street

Woolloomooloo, NSW



230p arrival, May 8 - 12

The public transport card here is called “myki” - again, I feel it’s worth having, but obviously up to you guys!

Wine Tasting in Victoria is in The Yarra Valley... plenty of options with this, they just depend on what you’re in the mood for. It’s only like an hour’s drive.

Rise Nation

You should totally do a versa-climber workout here!! Only 30 minutes, but around 400 calories. Yeah, it’s that intense - when I haven’t done it in a while, my feet go numb in my first climb. Say you know Adam Goldstein from West Hollywood - you’ll blow their minds, he’s my old roommate & dear friend. We used to have matching “his & hers’ Priai (that’s what we called our multiple Priuses... mine was white & his was dark graphite grey... Hahaha!)

The Como

299 Toorak Road

Melbourne, VIC


Staying in Southbank is awesome! I usually stay on Collins Street on the other side of the Yarra, (or with whatever friends) but you’re closer to the Australian Centre for Contemporary Art & the Royal Botanic Gardens here. And The Crown Casino! (I forgot to tell you The Star is 1 casino in Sydney, or Barangaroo might be open now too, BIG controversy - both at Darling Habrour.)

The Great Ocean Road is like driving Highway 1 to Big Sur - I recommend my cousins’ place at Bells Beach, Torquay: if this interests you let me know & I’ll make the intro.

The Olsen (hotel)

637 Chapel Street

South Yarra, VIC


I have a number of books John’s written out to me so I adore plugging his work & his frogs! I worked for his manager, who is one of my mentors as mentioned... but he’s usually outside of Alice Springs on an Outpost or a Community - or in London these days.

Happy to introduce you to Robert Doble & Simon Strong & Yasmin Nguyen if you fancy meeting up with them... All amazing humans: a painter, a photographer, & a writer/gallery/magazine owner.

Collingwood & Fitzroy are great for fashion like Paddington (or “Paddo” for short, in Sydney). You’ll learn the AFL footy culture here for sure… LOL

Triple J Radio is what most people surrounding our generation listen to... they have great podcasts to get you an idea - my favorite is “Like A Version” or “Live at The Wireless” - look up Halsey doing Justin Beiber’s “You Should Go & Fuck Yourself”, it’s the first time I ever heard her. Loves it!!

Definitely listen to/read Bill Bryson’s “In A Sunburned Country”/“Down Under” - I swear it will get you so excited to get there!

Okay, I’ll stop here but of course let me know of anything else I can help with.

I wish you both the most AMAZING trip!!!


THAT is the comprehensive email I wrote out to a hot, native Angeleno I met one night down the street from my place at Morton’s in Beverly Hills. He and his roommate were heading Down Under for his 34th birthday trip & I offered to help him plan it out a bit better, as to maximize their limited 8 days of travel. Pretty effing sweet for a first-timer to land with 1/3 of the way around the world, right?


Help me out here, please? He thanked me profusely before leaving The States & said he very much wanted to take me out to dinner for my help, but that he also wanted to up my wine game - a love of his that I admitted to being entirely ignorant in the knowledge of. He was heavily texting me once he got there, thanking me immensely for the information I’d provided, passing along his roommate’s gratitude for all the goodnesses they’d enjoyed as well... And then that was it. A few days before he landed back in The States, I never heard from him again. Is he dead? Most likely not...

He just ghosted me. What. A. Basic. Fuckwit.

It is though, kind of a fun game to think about what happened when someone ghosts you, isn’t it? Like, did he fall in love with some Aussie chick after he left WiFi that last evening? Or did he and his platonic female roommate finally admit their undying love for one another whilst in another country? Is he just cheap & didn’t want to take me to dinner or buy me wine in return for my local knowledge? I even went as far as to inquire a couple months later about the thank you dinner he had promised me, via text... but no, just crickets. Never a response back. And here’s how I know he isn’t dead (which may sound a little morbid to you, but only if you don’t know what I endured in late 2015... <3 Love you Mitchy!): because mofo is still posting STORIES on his Instagram! #wanker

Anyway, if you or anyone you know is heading over to The Merry Ol’ Land of Oz, please! Use my suggestions! I’d rather they don’t go to waste along with the hope of dating a local whose family actually lives here.

And onto the next one...

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