The Royal Mile’s Side Streets and Stories: A Walking Tour with Context

The streets of Scotland’s capital have seen centuries of drama and intrigue. On this walking tour along Edinburgh’s Royal Mile, you’ll hear from literary historian and Context Travel expert, Jenny Lister, as she shines a spotlight on the royals, rogues, and ragamuffins that have given the city its character through history. You’ll hear about Scottish minister and reformer John Knox, literary legend Robert Fergusson, and King David I, as Jenny points out several landmarks that serve as stark reminders of Edinburgh’s tumultuous history.

Starting on Edinburgh Castle’s esplanade, at the top of the iconic Castle Rock, you’ll stroll through all four sections of the Royal Mile (Castlehill, Lawnmarket, High Street, and Canongate) to the Palace of Holyroodhouse. Along the way, you’ll notice the contrast between grand architecture and the city’s darker history, found in haunted alleyways and underground sites like Mary King’s Close. As you wind your way through the Mile’s various side streets (known as closes, courts, and wynds), you’ll hear about people from Edinburgh’s past, from plague victims to notorious figures like William Brodie, whose double life inspired literary classics including Robert Louis Stevenson’s The Strange Case of Dr. Jekyll and Mr. Hyde. By the time you finish the tour in the Physic Garden opposite the Scottish Parliament Building, you’ll have peeled back the layers of Edinburgh’s history, in which monarchs, religious reformers, and plague victims all played a part.

On this 90-minute Royal Mile walking tour, you’ll:

• See the Heart of Midlothian mosaic, which once marked the entrance to the Old Tolbooth, a courthouse and administrative building
• Spot the remnants of marriage lintels – inscriptions above doorways in newlyweds’ homes, containing the initials of the happy couple and a blessing
• Discover the dark history behind South Bridge’s 19 archways
• Picture what the medieval city looked like, and how much narrower the High Street was when stairways, shopping booths and galleries were attached to the houses
• Take in World’s End pub and hear how, for many Edinburgh residents, their world was limited to the Old Town
• Stroll along Victoria Terrace, one of the city’s most beautiful streets, full of quirky shops with colourful fronts
• Visit Riddle’s Court, an architectural gem, and an example of the finest living that sixteenth-century Edinburgh had to offer
• Take in Gladstone’s Land, a row of Victorian tenement housing
• Hear the origins behind the names of various side streets and alleys, including Advocate’s Close, Fleshmarket Close, Mylnes Court, and Lady Stair’s Close
• Find out about the prosecution of Scottish women accused of witchcraft in the Middle Ages outside the Witches Well

From the medieval streets of the Old Town to Edinburgh’s more modern cultural landscape, every corner of the city holds a tale waiting to be told. So join Jenny and discover the magic of Edinburgh.