Thomas Randolph plaque

Explorer Tom St Margaret's Chapel, Edinburgh Castle is tiny enough that the local sheep probably chewed through the windows on their way in. It’s been sitting there since forever, looking like a miniature house that got lost on a hillside. The acoustics are so tight you can hear your own thoughts echoing back at you. Get there early and have it all to yourself.

Explorer Tom Edinburgh Castle once hosted a dramatic incident involving a lost set of keys and a very angry porter, though everyone pretends it didn't happen. It’s sitting on that rock looking smug about its Iron Age roots. Have a sandwich here and call it a heritage lunch.

Explorer Tom Edinburgh Castle in Silhouette would review its own visitors by saying 'too loud, not enough hats, and why are you taking so many photos?' It looks like a black cutout against the sky, which is great for drama but terrible for checking if it’s raining. The shape is iconic, mostly because it’s sitting on top of a really big rock. Look up, the best bit is always higher than you think.

Explorer Tom Inside St Margaret's Chapel, Edinburgh, there was a bishop who refused to visit because he thought it looked too small for his ego. He probably just wanted a bigger throne, frankly. If it's closed, admire it from the road like a polite stalker.

Explorer Tom Edinburgh Castle, Governor's House is where the boss lived and probably spent most of his time worrying about whether the tea was good enough. If it won the lotto, it would buy a bigger sofa and a window that doesn’t leak when it rains, which happens often here. Bring a flask and pretend you own the whole place just for an afternoon.

Explorer Tom Governor's House in Edinburgh is claimed by at least three different locals to have been invented by their great-grandfather, which is a classic Edinburgh move and I love it for that reason. It’s a nice little building that has seen more political manoeuvring than most governments manage in a decade. Bring a pen

Explorer Tom Earl Haig is doing a bit of impressionist art, standing on his own two feet next to the road like he’s late for a very important meeting with history. The statue looks so confused about which way traffic flows that I think it’s just trying to hitchhike back to 1920s London. If you see him looking particularly grumpy, wave hello and pretend he didn’t ignore you because he was deep in thought. Stand

Explorer Tom Scottish National War Memorial is being very stern, which is ironic given it used to be a cow market. I bet one of those cows tried to buy the whole place with a milk cheque back in the day. Find a local and ask them the real story, then come back and tell me.

Explorer Tom Castle Rock in Edinburgh is locked in a bitter feud with the next village over who got here first. It keeps pointing at its old castle bones like they’re receipts in a court of law. The whole 'Rock' thing is a bit of an insult, really, given it’s just a big lump of stone. It probably thinks it’s more majestic than it actually is, which is why nobody listens to it. Look up

Explorer Tom Edinburgh Castle, Tattoo Store and Coal Yard is full of 16th-century bastions and 17th-century burials that definitely know where the secret tunnel to the pub is. I bet the coal was used for more than just heating; maybe they roasted marshmallows over the graves. Mind the nettles, they're the real guards here.

Explorer Tom Edinburgh, Johnston Terrace is handling its nosey neighbours by pretending not to be there at all! It’s got that look of 'I know what you did last summer' but won’t say it out loud. The architecture feels like it’s judging your outfit from behind the garden fence. Go on a wet day, it suits the mood.

Explorer Tom Princes Street Gardens has been sitting on brass buttons and musket balls for centuries, probably complaining about how many tourists step right over them every single day. It’s like finding a lost coin in your carpet, except this one’s been there since the medieval times and still hasn’t found its owner. If it rains, blame me.