Often overshadowed by dazzling Prahran, Windsor is an unpretentious neighbourhood based around the southern extension of fashionable Chapel Street. Snap up unique retro items at Windsor’s vintage clothing stores or spend some time relaxing with a cup of specialty coffee in one of the suburb’s cute cafés. You’ll also find galleries showing work by local artists, boutique fashion stores and timeless corner pubs.

Stroll down Chapel Street’s more bohemian end and discover an eclectic shopping strip, complete with second-hand clothing shops, independent designers and well-known label stores amid classic Victorian-era terrace shopfronts. Check out local galleries and welcoming artist-run spaces, such as the Windsor Workshop.

After a few hours of shopping, recline in one of Windsor’s fashionable cafés and peruse a menu offering seasonal produce, delicate sweets and locally roasted coffee. Windsor also has a selection of delicatessens, bakeries and simple fast-food restaurants.

In the evening, make the most of a warm summer night drinking local beers under the cabanas in the leafy Windsor Castle courtyard. Nightclubs, including gay clubs and chic lounges, can be found in the Prahran section of Chapel Street.

Located approximately 5 kilometres (3.1 miles) southeast of Melbourne’s CBD, Windsor is accessible via tram, train and car. Trains departing from Flinders Street Station will reach Windsor in around 20 minutes and a network of trams connect Chapel Street, High Street, Toorak Road and Commercial Road.

To the north of Windsor, find Prahran Market, a bustling marketplace that has been in operation since 1864. You can chat with the traders and stock up on fresh fruit and vegetables, artisanal cheeses and small goods. Windsor’s northern border, High Street, and its western border, Punt Road, also contain eclectic shopping precincts. Punt Road connects Windsor to colourful St. Kilda and tranquil Albert Park Lake.