Sorry my picture did not turn out very good on this question..le sigh. Love the milkshakes and thick shakes (as pictured) at Batch Burgers and Espresso at Kirribilli out of all places. It quenches the thirst, and I love the old school milk bottle designed cup to drink it out of.
I just went there recently. I found the place by chance. My husband had a burger and I had a Hot Dog. Loved it and we certainly will be back. It was nice to get the takeaway and eat it under the Harbour Bridge. Next time I must try the shakes!! I wish I read this earlier!
Call me crazy but I have never gone wrong with a shake from Wendy's. They have a variety of creative shakes in different categories, mega shakes, super shakes, thick shakes... My favourite is the mega crunchy shake, Delish!
The Milk Bar by Cafe Ish in Redfern have some of the craziest most amazing shakes! Also Reuben Hills in Surry Hills has some incredible shakes too, including a to-die-for salted caramel shake. They also have a vegemite and butterscotch flavour which I've yet to try but definitely colours me intrigued!
Milkshakes are a difficult one for me, as even places that do gluten free food often forget about the drinks. But Moo Burgers do gluten free milkshakes, and super tasty ones at that (I'm rather partial to both strawberry and caramel). Best of all, they are in multiple locations around Sydney: Manly, Coogee Beach, Bondi Beach, Newtown and Crows Nest.
N2 Extreme Gelato in Chinatown. They make their gelato with liquid Nitrogen and they have the craziest but the tastiest milkshake flavours. My favourite is sour cream and chocolate. Don't knock it 'til you try it! (Dw, they also have normal people flavours too!)
If you ever happen to find yourself in Annandale, head over to Black Toast on Booth st. They do fantastic Campos coffees but you really can't go past their milkshakes. They have just the right amount of thickness and are served in sizeable steel containers that keep them ice cold. I'm a big fan of their coffee milkshakes (not ice coffees - there's a difference!), and their classic strawberry and chocolate flavours are definitely the best I've had in a long time.