Melburnian Sheridan Wright gives her insider’s itinerary for Australia’s most eccentric, culture-hungry city. This time she journeys south of the river, in and around South Yarra, Prahan and St Kilda.  

The great river divide is the stuff of a modern Shakespearean battle. Even if you’re not a local you’re likely to be staunchly one or the other by the time you leave.

Conquering the south is mostly about planning, so start your morning early with a hearty breakfast and some garden views at a street-side table at The Botanical (169 Domain Road, South Yarra). Breakfast is served from 7am, giving you plenty of time to plan your attack. From here you can simply walk to the tram stop directly across the road and jump on a number eight tram that will take you to the corner of Chapel Street and Toorak Road.

You will want to start your damage from the northern end of the street. Favourites like Topshop, Mimco and Green with Envy have enough to keep shoppers busy for hours but don’t get distracted; you’ll want to head south and there’s a long way to go.

You might want to pick up some macarons from LuxBite (38 Toorak Road, South Yarra) for your mid-morning sugar hit first – the salted caramel is worthy of aria.

Drop into White Suede for statement winter leathers, or visit the frou-frou palace that is Alannah Hill. Collette Dinnigan is divine, but a little nerve-racking once you realise how much that delicate lace blouse you’re putting your paws on will put you back (be sure to wipe the macaron off your hands first).

As you make your way south be aware of the retail dead zone in the first section after Commercial Road… don’t panic, just keep walking – it gets better.

As the street blooms again towards the Windsor end you’ll notice a change in the vibe of retailers and customers. Gone are the immaculately presented blondes and tiny dogs and in their stead are antiques, vintage numbers and small-scale boutiques.

www.chapelstreet.com.au is worthy of a day unto itself; with hundreds of square metres of organised chaos, it’s a antique lover’s dream of furniture, jewellery, silk scarves and homewares beautifully presented and organised for the serious collector – with no dust in sight.

Stop in momentarily for a coffee and a snack at Tyranny of Distance (147 Union Street, Windsor) but make sure it’s only a snack, as you’ll need room for the Queensland Spanner Crab and a cheeky afternoon tipple at The Woods of Windsor (108 Chapel Street, Windsor) from 4pm.

To continue your exploration, hop on a number 79 tram to St Kilda. Take a stroll down Acland Street and visit Readings Bookstore (112 Acland Street, St Kilda); it’s a Melbourne institution and a Zen refuge after any busy day. As independent booksellers go, Readings wrote the, erm, book. Classics to guilty pleasures; novels to DIY; beautiful gifts, music and that amazing smell of fresh clean paper. Staff here know their stuff, so if you’re hunting for something be sure to enlist their help.

A visit to Luna Park (The Esplanade, St Kilda) is shamelessly touristy, however considering old moon face has just turned 100, it might be nice to say happy birthday with a sunset ride on the Ferris Wheel; it really is one of the best views of St Kilda.

Make the most of what’s left of the beautiful St Kilda sunset by heading to Jacka Boulevard and Stokehouse (30 Jacka Boulevard, St Kilda). The Van Halen family have recently completed a makeover on the heritage-listed property, now giving you the option of the more casual café style downstairs or traditionally classic fine dining with a view version above.

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