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

  • Henrietta is not a “grab your chook and go” situation. If the $2.5 million fit-out doesn’t draw you in, the garlicky aroma of toum, fresh bread and fire-grilled chicken surely will.

  • This beloved pub, around since the 1920s, lets you choose from two bars or an upscale restaurant. Pile in for elevated pub classics, such as juicy steak with chips stacked like Jenga. Plus, there’s a deck for sunnier days.

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  • Pop into this warm, retro-feel restaurant for weeknight dinners of 72-hour-fermented focaccia, handmade pasta and woodfired meats. On weekends, party in the basement with amaro cocktails and DJs spinning Italo disco.

  • A sleek wine bar and restaurant serving up Middle Eastern-inspired dishes, some borrowed from its elder sibling Maha. Tuck into share plates of Armenian beef dumplings, lamb cutlets and taramasalata fried buns. There’s also a 120-strong wine list.

  • Short for “small eco-footprint”, this pizzeria is mostly vego – but when there is meat, it’s locally sourced. It’s also completely glass-free (all drinks are poured from a tap), and staff can deliver your pizza to nearby Victoria Gardens.

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

  • A buzzing food and beer hall inspired by Singaporean and Malaysian hawker halls. Work your way through a hit-list of hawker market dishes. Expect various dishes of noodles, rice, roti and curry (from the trusted team behind Chin Chin, Society and Baby Pizza). Plus, order lots of easy-drinking beers.

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  • The Kathmandu-born chef behind Lah Bros is showing that Nepali food is more than just momos. Enjoy regional specialities including bara, a crisp-fried lentil pancake, and a Nepali-style crème brûlée spinoff.

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  • A traditional Italian restaurant in the heart of Chapel Street.

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  • Healthy fish and chips on the go.

  • Colourful, neon-lit and always a party. Go for Japanese fusion including salty edamame, crunchy karaage and the ever-popular salmon and nori taco. Plus: frozen and fruity cocktails, sake and umeshu, and a tight Japanese whisky list.

  • Enjoy Japanese-inspired food at this moodily lit diner, from the team behind Saigon Sally and Hanoi Hannah. The stars here are crisped-up sticky eggplant, karaage chicken, miso-baked cauliflower and tender duck breast in brothy udon.

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  • This is the third Farro pizzeria, and it delivers the same level of polish as its siblings. Step inside for great Italian cocktails, an extensive range of pizzas – all of which can be made gluten-free or vegan – plus pastas and antipasti.

  • This spot from the Hanoi Hannah and Tokyo Tina crew is all about spicy birds: with a Vietnamese take on duck à l’orange and charcoal chicken with burnt chilli. Plus, there’s cocktails made with charred grapefruit and burnt plums.

  • Bimbo Deluxe pioneered the beer-and-$4-pizza formula. Lucky Coq replicates it just as well.

  • A strong player in the city’s crop of sharp, contemporary Italian joints. Find classic dishes with subtle twists, and a wine list that picks from the country’s premier growing regions. The commanding terrazzo bar is the best place to take it all in.

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  • Creative Californian-Japanese food among 1960s Japanese art and modern, plush surroundings.

  • Fish and chips, but not like the old days.

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  • A Chapel Street stalwart you can rely on.

Cafes

  • At this frozen desserts store by pastry chef Christy Tania, bestselling ice-creams include the pavlova and cookies and cream flavours. But don’t miss out on the range of ice-cream cakes, babkas and macarons either.

  • Scandinavian open sandwiches and clean, modernist design. And cocktails, too.

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  • A beautifully-designed cafe backed by Dukes Coffee Roasters.

Bars

  • This quirky lime castle is an improbable oasis away from bustling Chapel Street, and it has a huge courtyard. During the warmer months it’s thronged with locals, all drinking iced beverages and frosty beers.

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  • A gleaming 100-litre still sits at the centre of this red-accented bar and restaurant. It’s where distiller (and chef) Carlo Tran makes the gin you’ll find in your Asian-inspired cocktails – most of which are on tap. Pair them with pan-Asian dishes such as chargrilled prawns, beef rendang, deconstructed bao and karaage chicken.

  • Everyone (and their dog) is welcome at this bar, inspired by a short-lived Italian micronation from the ’60s. BYO food, enjoy Victorian brewers on tap, have a glass of natural wine and hang out with the locals.

  • This two-storey joint is warmly lit and moody, with long timber tables and cosy booths. Order Mediterranean-style share plates, choose a bottle (or three) from the wall, and tuck in with your favourite people. Neptune seats up to 105 people.

  • Hit this airy warehouse for natural wine and limoncello slushies on tap, pop-up kitchen takeovers, late-night DJ sessions and rotating artist residencies – all courtesy of Nic Coulter, co-owner of the adjacent Neptune Food & Wine.

  • An old-world Polish vodka bar and restaurant.

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  • Channel your inner flapper to live jazz, cabaret and drag performances, with a Charlie Chaplin cocktail in hand at this art-deco lounge.

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

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

  • An upstairs bar housed in the converted attic above Fonda Windsor.

  • Speakeasy-style bar and restaurant with a knack for pouring good whisky.

Shops

  • This bold and glitzy vintage store is one of Melbourne's most iconic. It showcases retro pieces from many eras, be it an ’80s leather jacket, a ’60s day dress or a contemporary rhinestone-encrusted number. Plus, plenty of bright shoes, bags and accessories to complete your look.

  • With sandstone, dark timber and reclaimed terracotta, the first shopfront for trans-seasonal womenswear label Elka feels almost like a luxury villa in Spain or Italy.

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

  • Bespoke suits and shirts from extremely well dressed tailors.

  • Casual daywear and accessories from Elwood Apparel Co.

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

  • A local corner-shop deli with a few seats for lunch.