Few Edinburghers live in the Old Town, but its labyrinth of dank alleys and steep streets suggests this was not always the case. Today, it’s mostly visitors, tartan-flavoured souvenir shops, and pipers that you’ll find on its cobbled streets. This is the place to get a feel for Auld Reekie (Old Smelly), as the town was once nicknamed, and stroll the Royal Mile, the thoroughfare that links the castle with the royal palace – two of Edinburgh’s great set-piece attractions. But there’s lots more exploring to do here down dozens of little alleys, or wynds, while at night the city’s busiest clubs erupt along the Cowgate which is closed to traffic for this purpose.

Suits and shopping bags rule the streets of New Town, until after dark when strappy dresses come out to play. This is the city’s central business district with its smaller offices, clothes boutiques, and many of the city’s flashiest restaurants and ritziest clubs. The architecture along roads like George Street helps give it a swank and formal feel: it’s a planned Georgian development of regal townhouses, geometric squares, and self-important statues. But it’s also a very wanderable neighbourhood, with a healthy bustle at almost any time of day and fine people-watching in places like St Andrew's Square which fills with picnickers around lunch. You’ll also find a series of cheerful basement bistros on Hanover Street, while dark Rose Street has something of the feel of an undiscovered back alley and is chock-full of characterful pubs and small independent shops.

Prevailing winds meant that most cities that grew in industrial Britain had their most desirable neighbourhoods to the west – upwind of factory fumes. Edinburgh was no exception, with its wealthiest citizens settling in its West End and leaving behind grand Georgian townhouses, private gardens and genteel crescents. These backstreets remain as dignified and sleepy as ever, and most of the action here lies along the district’s busy main roads. Lothian Road connects to southern Edinburgh and harbors a vague entertainment district: three theatres and the city’s main indie cinema. All attract a select crowd, the sort who appreciate the Saturday Edinburgh’s Farmers’ Market around the corner. The West End’s other great thoroughfare, Shandwick Place, is dominated by trams trundling out to the suburbs and airport, and shoppers picking up last-minute items before hopping aboard.

Glaswegians tease Edinburghers that their High Street is only half one, since buildings only line one side. But what they don’t say is how extraordinary the views are from Princes Street as a result. From here you look onto expansive and decorative public gardens beneath the mighty basalt cliffs on which Edinburgh’s Castle stands proud above the rest of the dramatic old town skyline. Yet many of those on Princes Street look the other way, as they’re concerned with chain store shopping or catching the tram or a train at main train station Waverley. But it’s not all utility here; the Scottish National Gallery rewards purposeless wandering, and December’s huge winter market in the gardens begins a season of revelry which ends with Hogmanay, Britain’s largest New Year’s street party.

Lying where grandiose New Town townhouses give way to malls and utilitarian housing, Broughton and Calton have long been transitional neighbourhoods with a mixed identity. It’s here that Edinburgh’s gay village found a home in the 1980s. But gay culture is anything but overt along bustling epicentre Broughton Street; even if polished pubs, hip bistros, smart delis and art galleries all speak of affluent good taste. The top of Leith Walk is more ragged. This major thoroughfare boasts a famously gritty gay club, as well as a strip of good Indian restaurants. Regal Georgian and Victorian townhouses preside over largely deserted streets in Calton, where only the occasional restaurant or hotel brings much life. Even so, a steady trickle of idlers and picnickers pass by to climb Calton Hill for its wide-open lawns, wonderful city views, and curious monuments – an Athenian-style temple among them.

Just downhill of New Town and attractively straddling a river near the elegant Royal Botanic Garden, it’s small wonder that Stockbridge became one of the city’s first hip neighbourhoods. It’s now one of Edinburgh’s most desirable, though many bohemian touches have fallen away as its residents have matured and the area has gentrified. Some second-hand shops cling on, but mostly residents display refined tastes in basement bistros, gastropubs, coffee and antique shops, boutiques and delis and at the Sunday farmers' market. A pleasant ten-minute walk away, along a leafy riverside path beside the gurgling Water of Leith, lies Dean Village. This sleepy neighborhood of medieval half-timbered houses still retains much of the village feel it had when watermills plied their trade here. Beyond, the wooded riverside path feels even more remote as it climbs to the sculpture gardens of the Scottish National Gallery of Modern Art.