Welcome to the new playground of the urban hipster. Once the gritty afterthought to polished South Yarra and bohemian Prahran, this inner-Melbourne suburb now has a cool line-up of bars, restaurants, independent fashion boutiques and galleries.
Two Lost Boys
Tucked away in a quiet dead-end street overlooking Windsor Railway Station, this ultra-cute pit stop is the spiritual home of the all-day breakfast. Posh toasties such as pear, gorgonzola and rocket with balsamic are a house specialty. It also caters to the city’s brunch-time obsession with an excellent avocado smash.
An infectious party vibe accessorises perfectly with the hawker ethos at this smart warehouse conversion from The Lucas Group stable (Chin Chin, Kong, Kisumé). Chop-socky food runs the Singapore-Malay gamut from satays to dumplings and curries, backed by about 20 beer taps and a cocktail list as dressed to impress as the diners.
An Insta-favourite when it opened midyear, this High Street newcomer specialises in the fruits of the sea, from quality tinned Spanish cockles – served with crisps and caper sauce – to snapper crudo dotted with finger lime and whipped roe anointed with bottarga. Fancy an après-dinner drink? Just head upstairs to the equally slick cocktail bar.
A venue that sums up Windsor’s irreverent appeal, Jungle Boy is a secret tiki bar accessed via a fridge door at the back of the Boston Sub sandwich shop. Not so secret? The quality of its cocktails (try the refreshing Watermelon Paloma with tequila, lemon and rose syrup) and the crazy vibe of this plant-filled wonderland.
A proper grown-up wine bar with plenty of vinous curios and switched-on service, the Lady shows just how far Windsor has come. Choose from an ever-changing list of 24 wines by the glass then sit on a stool by the window for a gander at the neighbourhood’s human zoo.
Let’s face it: the one thing Windsor is missing is a really great hotel. Lucky, then, that one of Melbourne’s best – the Art Series Hotel Group’s Cullen – is a short stroll away on Commercial Road in Prahran. This bright, modern hotel is decorated with works by its namesake avant-garde artist, the late Adam Cullen.
Hit the flicks
Built in 1936, The Astor Theatre is a city icon. The single-screen Art Deco gem specialises in classic and cult films, while the handmade choc-tops are second to none.
Shop, don’t stop
The eclectic end of Chapel Street is a vintage-shopper’s dream. Choose from endless rows of preloved cowboy boots at Vintage Sole or pick up a 1970s Pucci scarf at Shag. Various bric-a-brac shops sell tchotchkes for the perfect souvenir or memento.
But first, caffeine…
Small but well formed, Soldier On takes a democratic approach to the perfect brew, rotating the beans of Melbourne’s best roasteries.