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Need Edinburgh - London Planning and Train Advice

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We (DH, DS and myself) will be traveling from London to Edinburgh in a couple of months. We want to spend four nights in London, and have to be in Edinburgh by the fifth night, but I'm thinking of carving out some time on the train trip between the two locations to visit York.

It looks like, due to discount pricing on the train tickets, that it's much wiser, budget-wise, for us to book our tickets as far ahead as possible, which of course negates our flexibility on our travel day. And it does seem, without leaving London too early or arriving in Edinburgh too late, we could spend a 1/2 day or so in York (and we can check our luggage at the train station). I know it's subjective, but will it be worth the hassle? I would like DS to have some time in a smaller place.

Any other suggestions for a 1/2 day in between? Maybe a smaller town, where DS can get a very small taste of English country life (DH and I have traveled in the countryside, but DS has not)? (Cambridge and Oxford have been voted out of the running, as DS will be spending all his time at University himself)

And then, on the return, I'm facing the same problem with flexibility. We must be in Edinburgh the day before we head home to the U.S. via Heathrow (late-day flight the following day), and we've decided to spend that last night in London, so we don't have to worry about getting to the airport . But, again, seems like we should book those return tickets from Edinburgh to London ahead of time, which will cause me stress, I know, as we have to business to finish up that morning in Edinburgh. What do people do who live there - just grit their teeth and spend a lot for a last-minute ticket, or are there some ways to obtain some flexibility on the tickets and ticket pricing that I don't know about?

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