Congratulations, you have selected perhaps the richest bar crawl of this series.

We’re calling “upper CBD” anything east of Swanston Street, which means rare spirits at Bijou Bottle Store, craft suds and hair metal at Heartbreaker and midnight Martinis at Angel Music Bar. If variety is the spice of life, the upper CBD is one hot jalapeño.

If there was ever a place to start a bar crawl, it’s City Wine Shop (159 Spring St, Melbourne, It’s known for outdoor seating that attracts a crowd during rain as much as it does shine. You’ll know you’re in the right place when you spy diners with freshly shucked oysters, whipped cod roe with blini and a glass of wine from an exceptional wine list. If nothing on the one-page menu takes your fancy, head inside and lift something like a bottle of Vignerons Schmölzer and Brown’s medium-bodied and delicious 2020 Somerset Chardonnay from the cellar and add $20 to the retail price to drink in-house. 

Pull into Pope Joan (16/45 Collins St, Melbourne, in the Sofitel building for the bacon sandwich, a mainstay of this cafe turned all-day diner. Pope Joan’s move from Brunswick expanded its hours, menu and wine list considerably, so you can enjoy your afternoon over a glass of perfectly gluggable 2021 Mutual Promise Garganega made from fruit grown at Darling Estate in the King Valley. 

From there it’s an easy stroll across the forecourt to Flinders Lane where you’ll find Andrew McConnell’s Cumulus Inc (45 Flinders Ln, Melbourne,, the original casual, all-day restaurant which still houses some of the hottest seats in Melbourne even after 13 years of operation. Sit at the bar and freshen up with a bottle of Billy Button’s ‘Wildflower’ prosecco – full of honeydew and green apple, but drier in style for extra smashability – or nip upstairs to its more drinks-focused Cumulus Up offshoot. 

Duck into Dessous (basement, 164 Flinders Ln, Melbourne,, a basement wine bar that’s having a moment with small Victorian producers, pouring wines by the glass from the likes of Athletes of Wine, Chalmers, Mac Forbes, Pennyweight and Reed.

For something a little different again, head to newcomer Bijou Bottle Store (194 Little Collins St, Melbourne, where you can grab a bottle from the cellar to drink in with a $20 corkage, or lucky-dip your way through a selection of glass-pours that changes every hour. Time your visit wisely and you might be able to dictate what’s opened next.

Take advantage of golden hour and sneak into Union Electric (13 Heffernan Ln, Melbourne, for a cocktail on the rooftop. The bar is known for its extensive collection of gin, so ask for a nip of Brogan’s Way, Four Pillars or MGC in your favourite cocktail.

Next, consider a stroll to Heartbreaker (234A Russell St, Melbourne, for a slice of American-style pizza, a bit of rock ’n’ roll, a game of pool and a cleansing beer. The taps and cans are always kept fresh and on rotation, so you might find something like the juicy Wolf of the Willows Pacific Sour or the hops-driven Hop Nation The Buzz American Red ale on the pour.

When you’re ready to settle in for some warm service and substantial Italian fare, pull up a stool at Ombra (76 Bourke St, Melbourne, and split a carafe of the 2015 Foster & Rocco Riserva Rosé made by chef-turned-sommelier-turned-winemaker Adam Foster. For a continuation on the Grossi theme, head down the alleyway to Arlechin (Mornane Pl, Melbourne, for a twirl of midnight spaghetti (happily available any time of the night), a Bolognese jaffle and a bottle of textured and generous Payten and Jones chardonnay (and if you’re keen to drop a few extra dollars, ask nicely, and you’ll receive the hefty encyclopaedia that is the full wine list from Arlechin and Ombra’s parent restaurant, Grossi Florentino).

When you’re ready for some good tunes from a serious sound system, an energetic crowd and enough space to boogie, stop into Angel Music Bar (12 Bourke St, Melbourne, and order a Peachy Apricot Spritz made with Marionette Peach and Apricot Brandy Liqueurs topped with Chalmers col fondo. If and when your feet start to hurt, make one last stop at Siglo (2/161 Spring St, Melbourne, where you can bask in the glow of Parliament House from one of Melbourne’s best rooftops and finish the night on a bottle of Mooroduc Estate, Place of Changing Winds or expand your choices by way of the attached Melbourne Supper Club cellar. 

By Jess Ho