How to Spend a Roaring 1920s Gatsby-Style Weekend in Melbourne

Melbourne has always preferred the side door.

The good rooms are upstairs, underground, through an arcade or behind an entrance with very little interest in announcing itself. Follow enough of them and the CBD begins slipping between decades. A copper lift groans upwards. Green marble catches the light. Somewhere below street level a bartender is making a martini with almost architectural precision. Somewhere else, a piano has started.

This is not a historical reenactment, and nobody needs a feather boa. Some of these rooms genuinely belong to the 1920s; others arrived before or after and simply understand the old pleasures exceptionally well. The thread is Melbourne itself: Art Deco façades, grand banking chambers, candlelit cellars, old theatres, Champagne, oysters, live jazz and the particular thrill of dressing slightly better than the occasion technically requires.

Begin Friday afternoon with the key to a 1929 apartment. Come Sunday, you may have ridden a vintage tram, eaten beneath soaring arches, bought a book you absolutely did not need and lost several hours to a room without windows. Gatsby would have coped beautifully.

Stay

The Martini Suite

There could hardly be a better headquarters for the weekend than the Martini Suite, four floors above Flinders Lane in Harry Norris’ extraordinary 1929 Majorca Building. Outside, the façade gleams blue with glazed faience tiles; inside, terrazzo, marble and old copper lifts do a fine job of making the present day seem temporarily negotiable. The apartment keeps its original steel-framed windows, high ceilings and polished timber floors, with its owners deliberately drawing on the Jazz Age in the restoration.

Drop the bags. Open the windows. Put something cold into something cut-glass. Flinders Lane is waiting below.

Majorca Building, Flinders Lane, Melbourne

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The Royce

Technically beyond the CBD grid, yes. Spiritually essential, also yes. The Royce occupies Melbourne’s former prestige automobile showroom and takes its cues directly from the golden age of the 1920s: wood panelling, chrome, monochrome marble, handsome curves and references to Rolls-Royce at almost every turn.

Friday is when things get especially good. At 6.30pm, the baby grand in The Showroom opens up for two hours of live jazz, best taken with a cocktail in hand and dinner on the way. Caviar is there for anyone inclined to make a night of it. Walk in for the music; book ahead if you plan on staying for dinner.

379 St Kilda Road, Melbourne

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Le Méridien Melbourne

Le Méridien Melbourne is the modern interpretation: sharper around the edges, more Paris-after-dark than faithful Jazz Age relic. Its most persuasive argument sits underground. Dolly deals in nostalgic European cooking and enough low-lit drama to make lunch above ground feel faintly administrative afterwards. On select Saturdays the room goes fully nocturnal with dinner, cocktails, supper and live jazz; the hotel itself warns that these nights fill quickly.

Upstairs, the rooftop looks towards Parliament House. Downstairs, the band is warming up. One could do worse.

20 Bourke Street, Melbourne

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Sip

Apollo Inn

Apollo Inn understands that the best cocktail bars need very little clutter. The room is intimate, the light is low and the drinks are taken seriously without anyone delivering a TED Talk over the ice. Its name reaches back to one of Melbourne’s earliest public houses, which opened nearby in 1844; Andrew McConnell’s modern incarnation is deliberately devoted to the old transaction between bartender, bar and drinker.

It is an excellent first drink: early enough that everyone still remembers their coat.

165 Flinders Lane, Melbourne

Eau-De-Vie

Then comes the speakeasy. Behind a heavy door in tiny Malthouse Lane, Eau-De-Vie remains gloriously committed to the bit: booths, waistcoats, a whisky room concealed behind a bookcase and bartenders willing to employ flame, smoke and liquid nitrogen in service of a drink. The whole place plays knowingly with Prohibition-era theatre, but more importantly, it has the drinks pedigree to survive long after “hidden bar” stopped being novel.

Have one excellent cocktail rather than four increasingly theoretical ones. There is a long night ahead.

Malthouse Lane, Melbourne

Nick & Nora’s

The decade edges into the 1930s at Nick & Nora’s, and nobody need alert the authorities.

Inspired by The Thin Man’s famously well-lubricated fictional couple, this Champagne and cocktail bar does post-Prohibition excess with a knowing hand: hundreds of bottles of bubbles, oysters, caviar, dark booths and three balconies above Benson Walk. Roaming saxophonists also appear on selected nights, bringing swing through the room rather than politely containing it to a stage.

A bottle of Champagne here has a way of deciding the rest of the evening for you.

11 Benson Walk, 80 Collins Street, Melbourne

Mill Place Merchants

Finding Mill Place Merchants is part of the fun. The bar occupies a heritage-listed 1840s building in a lane once busy with Melbourne’s hatters, soap makers, candle makers and traders. Today, stone and brick walls sit beneath chandeliers and marine lamps, with old furniture, dark corners and classical cocktails carrying some of that mercantile past into the night.

It is more theatrical than Apollo Inn, less committed to outright Prohibition cosplay than Eau-De-Vie, and especially good when the weather outside has turned miserable.

Which, in Melbourne, keeps the diary fairly open.

Ground Floor, 2 Mill Place, Melbourne

Siglo

There are few better places to remember that Melbourne is beautiful than Siglo after dark. Climb above the Melbourne Supper Club and emerge onto the open-air terrace facing the floodlit columns of Parliament House, St Patrick’s spire and the old domes of the Princess Theatre. The bar itself is contemporary, commissioned in 2007, so no historical fibs are required here. The pleasure is older: white-jacketed service, whisky sours, Champagne, wicker chairs and, for those so inclined, a cigar beneath the city lights.

Sitchu Tip: Stay until the city goes particularly gold around the edges.

Level 2, 161 Spring Street, Melbourne

Paris Cat Jazz Club

At some point, the soundtrack needs to stop being decorative. Paris Cat Jazz Club has been keeping Melbourne in live jazz since 2005, inside an 1895 warehouse in Goldie Place. Today it runs across three levels with two performance rooms and a serious program of jazz, soul and blues. Weekend shows frequently sell out, so this is one part of the evening worth organising before the first martini takes effect.

The tables are close. The room is dark. The music gets everybody’s full attention, precisely as it should.

6 Goldie Place, Melbourne

Savour

Gimlet at Cavendish House

If this entire exercise required one dining room to explain itself, Gimlet would probably manage. Cavendish House is a 1920s Melbourne landmark, its neo-Georgian and Art Deco details now framing Andrew McConnell’s grand European dining room. Inside: cherrywood, marble, curved booths, oysters, caviar, wood-fired meat and seafood, and a bar that knows its way around the classics.

Come dressed for dinner. Start at the bar. Finish there too if judgment has deserted you in an enjoyable way.

Sitchu Tip: Friday and Saturday supper runs until 1am, which is information worth filing away.

33 Russell Street, Melbourne

The Lodge Little Collins

Few recent Melbourne openings have handled history as well as The Lodge Little Collins, which has taken over a Harry Norris-designed Art Deco landmark and filled four floors with fashion, wine and food.

Upstairs, the Dining Room is framed by enormous arched windows and antique mirrors; underground, the Cellar Wine Bar turns darker and louder, with checkerboard floors, pasta, wine and cocktails.

Shop downstairs before lunch and emerge several hours later having somehow acquired both a jacket and a bar tab.

280 Little Collins Street, Melbourne

Society

There is nothing historically 1920s about Society, and pretending otherwise would be silly. But it earns its seat at the table because it understands the supper-club side of the assignment: hand-cut crystal chandeliers, white-gloved tableside service, plush seating, a cellar exceeding 10,000 bottles and the faint sense that an ordinary Tuesday could get expensive very quickly. Seafood, handmade pasta and wood-fired meats keep the menu firmly in European territory.

Gatsby by temperament, then, rather than birth certificate.

80 Collins Street, Melbourne

Grill Americano

If Fitzgerald had made it to Melbourne by way of Milan, Grill Americano might have kept him busy. The room is all height and proportion, anchored by a vast marble bar and an open kitchen working across charcoal, wood fire and steam. Northern Italian cooking runs through bistecca, seafood, handmade pasta and the sort of desserts that make declining pudding feel needlessly puritanical.

Martinis are very much at home here. So are excellent shoes.

112 Flinders Lane, Melbourne

Reine & La Rue

The building predates Gatsby by several decades, but Reine & La Rue offers something harder to manufacture than a theme: actual grandeur.

The restaurant inhabits the Cathedral Room of Melbourne’s former stock exchange, behind the great banking chamber at Collins and Queen. Arches climb overhead, stone columns line the room and French cooking arrives beneath a ceiling that makes most modern restaurants appear slightly underdressed. There are oysters, foie gras, dry-aged beef, French wine and an eight-seat bar called La Rue hidden off the courtyard. On Sundays, the restaurant also runs Jazz Du Dimanche.

A useful room for remembering Melbourne once built banks like cathedrals, and that a Sunday afternoon can still disappear beneath stone arches, French wine and jazz.

380 Collins Street, Melbourne

Dessous

The night should, at some point, go underground. Dessous occupies the basement of the historic Richard Allen & Son building, all marble, deep greens, velvet booths and low lamplight, with the faintly disreputable air of a hotel bar after everyone respectable has gone home. Oysters and spanner crab doughnuts crowned with salmon caviar keep company with martinis and a European-leaning late-night menu, with the kitchen running until midnight.

This is the party after the party: ties loosened, another drink appearing at the bar and very little appetite for going home.

164 Flinders Lane, Melbourne

Promenade & Peruse

Follow Melbourne’s Interwar Architecture

The secret to this weekend is looking up. Begin with the Majorca Building on Flinders Lane, Harry Norris’s late-1920s confection of blue faience, arches and Moorish-inflected ornament. Then wander over to his Nicholas Building. Completed in 1926, its Cathedral Arcade still runs beneath a vaulted and domed leadlight ceiling — a rather fabulous reminder that Melbourne once considered even popping into the shops worthy of architectural ceremony.

Sitchu Tip: Stop at Cathedral Coffee while you’re in the Nicholas Building, a tiny cafe and wine bar set right beneath all that leadlight. Coffee if it’s early; a glass of something interesting if the afternoon has begun to get ideas.

A few blocks away, Forum Melbourne takes 1929 and runs riot with it: minarets and gargoyles outside; columns, statuary and a ceiling scattered with tiny lights to resemble a European courtyard beneath a twilight sky inside. It opened as the State Theatre at the very end of the decade, apparently with no interest whatsoever in restraint.

Keep an eye out for the theatres, too. The Comedy Theatre arrived in 1928 in a flourish of Florentine arches and Spanish-inflected interiors; a year later, the Regent Theatre opened on Collins Street with enough rococo ornament to make restraint seem terribly unfashionable.

Finish at the Manchester Unity Building, the magnificent 1932 epilogue. Marcus Barlow looked to Chicago’s Tribune Tower for inspiration and designed a commercial Gothic skyscraper complete with a soaring corner tower, marble, mosaics and Melbourne’s first escalators. By then, the Depression had arrived, but somebody had evidently forgotten to tell the architect.

Majorca Building, 258–260 Flinders Lane, Melbourne

Nicholas Building, 37 Swanston Street, Melbourne

Cathedral Coffee, Unit 9, Cathedral Arcade, Nicholas Building, 37 Swanston Street, Melbourne

Forum Melbourne, 154 Flinders Street, Melbourne

Comedy Theatre, 240 Exhibition Street, Melbourne

Regent Theatre, 191 Collins Street, Melbourne

Manchester Unity Building, 220 Collins Street, Melbourne

Go Window Shopping Through Old Melbourne

Melbourne understood the pleasure of shopping long before retail acquired mood lighting and a brand strategy. Start beneath the glass roof of the Royal Arcade, where Gog and Magog have been thumping out the hour above Gaunt’s Clock since 1892, then cross Collins Street for the Block Arcade: mosaic floors, stained glass and a domed canopy borrowed, rather grandly, from Milan’s Galleria Vittorio Emanuele II. Neither is a child of the 1920s, but by then both were already old hands at the Saturday ritual: dress well, take tea, inspect the windows, be seen doing it.

And beneath the clocks at Flinders Street Station, City Hatters has been selling hats since 1910. Gatsby could, quite literally, have shopped there. From there, continue the performance on Bourke Street. Myer’s city store dates to 1914, with David Jones keeping the grand department-store tradition alive nearby. Take your time. Try on the coat that requires a better life. There is no prize for efficiency here.

Then let 2026 barge in. MECCA Bourke Street now spreads across three floors of perfume, flowers, treatments and enough beauty to lose all sense of fiscal responsibility. Even better, it occupies the former site of E.W. Cole’s famously eccentric Book Arcade, once the largest bookstore in the world.

Different century, same Melbourne instinct: dress it up, make a spectacle of it and lose the afternoon.

Melbourne CBD

Browse Melbourne’s Great Bookshops

Begin at Hill of Content, Melbourne’s oldest bookshop, founded in 1922 and still presiding over Bourke Street more than a century later. Browse the new releases, climb the stairs, leave with something you had absolutely no intention of buying. This is, after all, a lost weekend. Planning has already failed.

Then save Paperback Bookshop for after dark. It has occupied the quieter end of Bourke Street since the mid-1960s, when its original owner began importing the books Melbourne readers struggled to find: the Beats, new Australian writing, titles caught in the censorship net. Some of those original shelves remain, now crowded with fiction, poetry, politics, art, film and whatever the booksellers have decided deserves the space.

Come after the theatre, before a drink at Siglo, or simply because buying a novel at 10.30pm feels like the sort of civilised city behaviour worth protecting. On Fridays and Saturdays, the doors stay open until 11.

Buy one on optimism. Carry it around all weekend. Read seven pages.

Hill of Content, 86 Bourke Street, Melbourne

Paperback Bookshop, 60 Bourke Street, Melbourne

Build a Queen Victoria Market Picnic

There should be one meal that requires no maître d’. Collect bread, cheese, charcuterie, fruit and something sweet from Queen Victoria Market, then carry the haul to Carlton Gardens and spread it out beneath the trees. After a night of Champagne and white tablecloths, a paper-wrapped lunch feels almost medicinal.

Queen Street, Melbourne

Visit the State Library

Walk into the La Trobe Reading Room at the State Library Victoria and let the room do the work: the great white dome overhead, green lamps below, people bent over books in concentric rings. It predates the Jazz Age, but that hardly matters. The fantasy here is not flappers. It is having three uninterrupted hours to read in a beautiful room and perhaps a family fortune somewhere handling the bills.

328 Swanston Street, Melbourne

Take a Seaside Promenade Through St Kilda

By Sunday, take the party to the sea. St Kilda wears its history loosely: interwar apartment blocks, palms, old villas and Deco curves spilling towards Port Phillip Bay. Luna Park had already been grinning over the foreshore since 1912, and by the 1920s this was Melbourne’s great seaside playground.

Start in Catani Gardens, walk out along St Kilda Pier, then follow the foreshore back towards the Palais Theatre, its grand domed façade looking remarkably close to how it did when the theatre opened in 1927.

From there, head inland to The Astor, which picks up the story in 1936. Its grand staircase, dress circle and golden curtains remain gloriously intact. Catch an old film if the timing works; otherwise, keep walking until the sea air has dealt with last night’s martinis.

Luna Park, 18 Lower Esplanade, St Kilda

Palais Theatre, Lower Esplanade & Cavell Street, St Kilda

The Astor Theatre, Corner Chapel Street & Dandenong Road, St Kilda

Catch an Old Flick at The Capitol

Then come the picture palaces. The Capitol opened in 1924, the work of Walter Burley Griffin and Marion Mahony Griffin, and a century later its ceiling still looks faintly impossible: a great crystalline canopy of geometric forms once illuminated in shifting colours during the silent-film era.

Find a screening, settle beneath it and let the lights go down. For a couple of hours, Swanston Street can wait outside.

The Walk Arcade, 113 Swanston Street, Melbourne

Take the Long Way Through the Gardens

By late morning, the sensible thing is fresh air and an unnecessarily elegant walk. Cross Princes Bridge, leave the city behind by degrees and follow the river towards the Royal Botanic Gardens, where lawns fall towards Ornamental Lake and old paths disappear beneath enormous trees. Melbourne has been promenading here for generations; once, Sunday riders even circled the Tan on horseback.

Pass the Temple of the Winds, stop above the river, then keep going without consulting the clock. Sunglasses help. So does a good coat. With 38 hectares of gardens between you and the city, lunch can wait a little longer. Sunday could do considerably worse.

Ride the City Circle Tram

For an hour, let Melbourne come to you.

The free City Circle Tram still makes its clockwise circuit aboard the city’s historic W-class trams, rattling along Flinders, Spring and La Trobe streets before swinging through Docklands. Climb aboard, take a window seat and listen as the recorded commentary points out the old buildings slipping past outside.

There are faster ways to cross the city. Very few are this handsome. By the time you step off, the decades should be nicely confused.

By Sunday afternoon, Melbourne has returned to itself: takeaway coffees, impatient trams, somebody running for a light they will not make. But once you have spent a weekend looking for the older city, it becomes difficult to stop seeing it — the blue tiles above Flinders Lane, the theatre ceilings, the banking chambers, the bars below street level.

The trick was never to pretend it is 1929. It is knowing exactly where 1929 never quite left. For more fun and frivolity through the CBD, explore these standout restaurants and beautifully designed hotels worth making a night of.