The Rocks is a world away from its rough and tumble beginnings when working girls battled it out for business in the cobbled alleyways and slums as sailors stoushed after one too many brews. But while the historical heart of Sydney isn’t as gritty as it once was, the city’s oldest and most loved precinct, is no less lively. A little pocket of rich and risqué history that began with the first European settlers and British convicts in 1788, The Rocks today is also one of the most beautiful.

Perched on the edge of the CBD and tucked under the iconic Sydney Harbour Bridge, the Rocks is made up of landmark laneways and heritage buildings dating from the earliest days of the colonies. Once you have secured one of the several luxury Rocks Hotels, a visit should start and end, on foot. Getting lost in the cobbled streets is part of the fun.  If you want to knock over a few note-worthy spots, there’s plenty of historical walks that will take in some of the area’s richest history, such as the Susannah Place Terraces and Cadmans Cottage, offering you a glimpse of the working class life of the area which maintained its rough reputation until the late 1870s. But if you find all that walking thirsty work, there’s a classic Aussie pub on almost every corner.

The Lord Nelson and The Fortune of War both claim to be Sydney’s oldest watering holes but owning this crown doesn’t really matter because whether it’s a weekday drink when the city suits spill out onto the sidewalks or weekends when music and beer make fine companions, if you’re in the mood for fun, the old-world Aussie pub charm is at its best. The Mercantile, Orient, Palisades, The Australian and even the Hero of Waterloo are also full to bursting most nights of the week in a riot of revelry. For a modern twist pop into the Argyle, a vast expanse of indoor and outdoor space dedicated to music and mayhem.

Managing the effects of the night before is easy with everything from pancake parlours to rustic courtyard garden restaurants, upmarket Thai eateries, French pastry shops, authentic Aussie pub grub, a Bavarian bier café or any number of upmarket harbourside eateries. The Rocks markets at weekends have become a vital part of Sydney weekend life with hundreds of visitors buzzing around more than 200 stalls showcasing food, fashion, jewellery and art, with many unique Aussie products.

But no visit would be complete without climbing the famous Sydney Harbour Bridge. There’s no need to fear heights though, you’re harnessed all the way and even for a local it’s one of the best things you’ll ever do. Alternatively for just $9.50 you can climb the 200 steps to the open air observation deck of the famous bridge’s southeast pylon. At 89m high the pylon lookout is 45m shorter than the bridge’s summit. Even cheaper still? You can just walk across the bridge from The Rocks to Milsons Point and back again for free.

And for me, there’s only one way to celebrate such an experience – with lunch on the rooftop of Sydney’s best kept secret – the Glenmore Rd pub.
For just $16.50, you’ll get a huge feed of fabulous fish and chips with a great vibe and the best views of Sydney – albeit through a wire fence past the Rocks rooftops to the harbour - where the old green and yellow Sydney ferries bustle busily across the twinkling harbour and the sun sparkles off the majestic sails of the Opera house. It’s simply magic.

See also: The Rocks Accommodation, Australian Heritage Hotel, Russell Hotel, Regis on Castlereagh, City Lodge Hotel, Metro Hotel Sydney, The Menzies Hotel Sydney, Sydney City Hotels.