After a long time in the shadow of ‘older sister’ Prahran, Windsor’s time is now. One stop further down the Sandringham train line, Windsor impresses with its cheerful mix of designer boutiques, gastro pubs and brekky hotspots, Op Shops, retro stores and some of the best Asian food in the inner south. 

Matinees and double features

Standing tall on the intersection of Princes Highway and Chapel Street, the Astor Theatre has been serving up ‘fine film and atmosphere since 1936’. Catch festival showings, classics and cult reruns amid the splendour of the art deco interiors. Jules e Jim anyone? 

Retailing southside

Walk the ‘vintage mile’ on the south end of Chapel, taking in antique stores, Op Shops and second-hand boutiques. Find that unique trinket, party dress-ups, or save a few pennies on pre-loved furniture. 

If you’re looking to smarten up your wardrobe, you’re in the right neck of the woods too. Stroll into Gorman on Chapel and strut out wearing the latest colours and shapes. Design a Space showcases the work of some of Melbourne’s best young designers. 

Foodies ahoy

Explore the area's dining scene and you're bound to find a place with your name on it. Siblings Tokyo Tina and Hanoi Hannah are the name of the game for contemporary Asian, along with Hawker Hall and playful Mr Miyagi.  

Dose up on Mexican chilli at Fonda's Windsor chapter, or keep it real at local haunt The Wolf and I.  

Morning-after brekky options abound, with Yellow bird café, Tyranny of Distance and School of 7 Bells keeping the morning crowds happy. Afternoon sugar hits come from Pidapipó Windsor’s gelato delights. 

Raising the bar

Spend summer evenings in the beer garden cabanas at the Windsor Castle, or go for speakeasy style and single malts at Woods of Windsor. Sop up the vodka with scrumptious sausages and dumplings at Borsch, Vodka & Tears.

Jungle Boy offers tropical fever dreams to those in the mood, while a quieter evening awaits at Ines Wine Bar, where you can savour French, Italian and local Victorian wines.  

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