Beyond the gardens south-east of the CBD are some of the city’s most exclusive suburbs: South Yarra, Toorak, Malvern and Armadale. South Yarra and Toorak centre around Toorak Road, where exclusive clothing and footwear stores, as well as cafes and food shops, line the street. Over Williams Road in Toorak, a quaint Tudoresque shopping village houses more top shops (make sure to visit Simon Johnson for gourmet products). Chapel Street runs in the other direction, from South Yarra into St Kilda, and is virtually non-stop shops for three major blocks, from Toorak Road to Dandenong Road .
The north of Chapel Street, between Toorak and Commercial roads, is the place to come for the latest in fashion – and you’ll probably want to dress up for the occasion. About halfway down this stretch is the Jam Factory, a shopping complex and food court inside the old premises of the Australian Jam Company. Facing the street is Borders bookshop, and inside is a cinema complex that screens most of the new releases as well as some arthouse titles.
Just around the corner from Chapel Street on Commercial Road is the Prahran Market, which is Australia’s oldest continually running market. It is a lively place with everything from gourmet potatoes to dolmades, coffee beans, fresh meat and cookware. 163 Commercial Rd, South Yarra; (03) 8290 8220; open dawn–5pm Tues, Thurs and Sat, dawn–6pm Fri, 10am–3pm Sun.
A little further up Chapel Street, Greville Street runs off to the west. The narrow strip is lined with cafes, bars, hip clothing shops and some of the original occupants such as the near-icon-status Greville Records. Much less edgy and alternative than it once was, it’s still worth a wander.
If the northern end of Chapel St is the fashion darling, the Prahran/Windsor end, south of Commercial Rd, is its more down-to-earth, homely sibling. Lined with dozens of interesting cafes, restaurants and shops, it’s a fantastic stretch to browse and graze; be sure not to miss the massive and bizarre Chapel St Bazaar, overflowing with retro clothes, furniture and homewares (you’ll be amazed and delighted by what you’ll find).
While mansions today boast home-entertainment systems and swimming pools, those of yesteryear had croquet lawns and ballrooms. Como House is a National Trust-listed mansion at the end of Williams Road. Stroll around the gardens and take a tour of the house, complete with the original furnishings of the Armytage family. You can visit the gorgeous cafe (open Wednesday to Sunday) without paying admission. Nearby is Como Landing, where you can take a punt across to Herring Island in the middle of the Yarra. This artificial island boasts a sculpture park and picnic/barbecue facilities. Como House, cnr Williams Rd and Lechlade Ave, South Yarra; (03) 9827 2500; open 10am–5pm daily; Herring Island punt noon–5pm Sat–Sun during daylight saving.

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