Windsor has long been overshadowed by its more flamboyant neighbours, Prahran and South Yarra. As recently as 2005, the bottom end of Chapel Street was mostly tired two-dollar shops and didn’t have much going for it.

You wouldn’t know it now – the suburb has developed one of the most dynamic restaurant scenes in Melbourne. And thanks to Jungle Boy and classics such as Lucky Coq and The Windsor Castle, it’s also a great place for a drink.

Wander away from Chapel Street and things get real quiet. The narrow streets mix ‘70s-era apartments, older terraces and a few newer developments, with few shops or other businesses. It’s a good place to live if you like to be close to the action, but not right in the thick of it.

Restaurants

Mr Miyagi

Restaurant

Sake and 80s throwbacks flow freely in this neon-lit Japanese eatery.

Boston Sub / Jungle Boy

Restaurant

A late-night sub shop with a tropical-themed cocktail bar hidden behind a coolroom door.

Good Nights

Restaurant

Under the light of a mirror ball enjoy DIY rice paper rolls; osso bucco congee with Chinese doughnuts; and a Black Angus, brisket and bone marrow pho.

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Maha East

Restaurant

A handsome, cosy space you can spend hours in traversing a menu of Middle Eastern favourites borrowed from its elder sibling, Maha.

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Sash Japanese

Restaurant

Sushi tacos, spicy prawn sliders, and two varieties of pizza in a dimly lit diner.

Tipico

Restaurant

A polished Italian diner that’s ditched the traditional red-and-white tablecloths for contemporary art and modern plating techniques.

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Cafes

Journeyman

Cafe

A beautifully-designed cafe backed by Dukes Coffee Roasters.

Glacé

Cafe

A frozen desserts store from pastry chef Christy Tania.

The School of 7 Bells

Cafe

A cosy cafe with the usuals, and the not-so-usuals.

Mr Mister

Cafe

You’ll feel refreshed as soon as you enter this bright, airy cafe.

Two Lost Boys

Cafe

Quality coffee and quick eats next to Windsor Station.

Bars

Chacho’s

Bar

Pizza and tequila meet head-on at this local haunt serving up late-night eats and tequila that’s meant for sipping, not slamming.

Galah

Bar

Natural wine, craft beer and cocktails with an Australian focus.

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Lover

Bar

A late-night dining spot with a playful but serious cocktail program.

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Back Bar

Bar

A cosy hidden gem behind the Tusk cafe with an extensive cocktail list.

Windsor Castle Hotel

Bar

This quirky lime castle with a huge courtyard is a getaway from bustling Chapel Street.

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Mothers Milk

Bar

A cosy, dark unmistakable bar down the Windsor end of Chapel Street.

Shops

The Lucy Folk Salon

Shop

The playful-luxe label has an outpost in Windsor selling its signature jewellery, sunnies and hand-loomed apparel, plus pieces from other designers.

P.Johnson Tailors

Shop

Bespoke suits and shirts from extremely well dressed tailors.

Shag

Shop

Like stepping into Grandma’s closet on the way to Narnia, Shag is a vintage treasure-trove showcasing retro pieces from many eras.

The Windsor Annex

Shop

Casual daywear and accessories from Elwood Apparel Co.

Chapel Street Cellars

Shop

More kinds of wine and beer than you can imagine – and you're welcome to drink in-house.

Plane

Shop

A clever play on the everyday "plain" clothes we all need.