My 'go to' is linen trousers, depending on the weather I can layer tights / leggings underneath, they can be worn for sight seeing or dinner somewhere smart.
When I was teaching this was my 'uniform' so I have four pairs.
Some sturdy ankle boots or good trainers for the sight seeing, something with heels for dinner?
A couple of scarfs / wraps that can make an extra warm layer or substitute for a cardigan for dinner.
I'd use the leggings and a T shirt to sleep in.
Assuming you are travelling by train.
Day one, travel in jeans and boots as these are the heavysest. I'd have a hat, brolly and gloves either packed or worn.
I'd pack in a rucksack, if you roll rather than fold things don't crease.
Get tot he hotel, drop bag, put o trainers and assess weather for hat / gloves / brolly
Take most things out of the bag, pack gloves, scarf, water bottle in rucksack and go sight seeing.
Back to the hotel to change for dinner, if you are eating where you are saying then linin trousers, smart T shirt or shirt, add heels and small bag.
Sleep in leggings and T shirt, laver trousers depending on weather.
Leave bag at the hotel or take it to station left luggage, go to show, back to station and home.