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Notes -
I can probably offer more specific recommendations if you let me know what your brother is interested in.
Glasgow has excellent nightlife! I've already seen someone nick a traffic cone and carry it off proudly beneath their armpit, and I can only describe the experience as akin to accidentally walking into a fairy tale. It turns out I actually like the city, and not just because it seems like a promising place to be a senior shrink.
I have no specific interest in Loch Ness, so if you think Glen Coe is better or less of a tourist trap, I'll prioritize it instead.
The best part of the castle was ignoring it, or at least the argument about medieval laws around monogamy that I won
I've been to York, but haven't really explored it. I'll put a pin in that and Bath, though I'd prefer a shower. Appreciate the suggestions!
Honestly speaking, my brother is a homebody, just like me. As long as we see scenic places and drink plenty of booze, we'll be content. All the more so if we can do both at the same time.
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