The Georgian New Town, Dean Village, Stockbridge and Leith

By the 1760s, the medieval Old Town was so overcrowded and smoky that the city drained the Nor' Loch marsh at the base of the Castle rock (now Princes Street Gardens) and held a competition to design a rational Enlightenment suburb to the north. Won by 22-year-old architect James Craig, the Georgian New Town remains the largest and best-preserved neo-classical townscape in Europe, and its western edge drops straight into the wooded river gorge of Dean Village.

Walking the New Town: Charlotte Square to Circus Lane

Start at the western end of George Street on Charlotte Square, whose northern side was designed as a unified palatial facade by Robert Adam in 1791 (you can step inside a restored 1790s aristocratic townhouse at The Georgian House, No. 7 Charlotte Square, and next door into Bute House, official residence of the First Minister of Scotland). From George Street, walk north down the slope toward the Firth of Forth through the sweeping residential crescents of the Second New Town (Moray Place, Ainslie Place and Royal Circus) and duck into the curving, cobble-paved mews alley of Circus Lane, where former coach houses and stables are draped in flower boxes beneath the spire of St Stephen's.

Dean Village, the Water of Leith and Stockbridge

Ten minutes west of Charlotte Square via the high arches of Thomas Telford's 1831 Dean Bridge, a cobbled lane drops steeply down to the river at Dean Village (Water of Leith Village). For over 800 years this picturesque hollow was a working water-milling settlement where eleven mills ground grain for Edinburgh's bakers:

• Well Court and Miller Row: stand on the small stone footbridge at Bell's Brae to photograph the red-sandstone clock tower and half-timbered arts-and-crafts courtyard of Well Court (built in 1886 as model housing for local workers) reflected in the rushing brown water of the weir.
• The Water of Leith Walkway to Stockbridge (20 minutes): from Miller Row, follow the signposted riverside path downstream through a steep, mossy woodland ravine past the classical mineral-spring rotunda of St Bernard's Well (crowned by a statue of Hygieia) until you emerge into Stockbridge.
• Stockbridge and the Royal Botanic Garden: grab a warm cheese scone or artisanal coffee on St Stephen Street or Raeburn Place (on Sundays, the Stockbridge Market fills Jubilee Gardens with Scottish street food, venison burgers and baking stalls), then walk ten minutes north to the 70-acre Royal Botanic Garden Edinburgh (free entry to the grounds) for its rock garden and terrace view back toward the Old Town skyline.

Down to the Coast: Leith and The Shore

From St Andrew Square or Picardy Place in the New Town, hop on the Edinburgh Tram (15 minutes) down Leith Walk to Edinburgh's historic port of Leith. Get off at The Shore to walk beside the old stone docks where 18th-century wine merchants unloaded claret from Bordeaux (now home to Edinburgh's highest concentration of Michelin-starred restaurants, seafood bistros and waterside pubs), or ride two stops further to Ocean Terminal to step aboard the Royal Yacht Britannia.