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Fine tuning our route through Scotland

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We are working on a trip to the UK next summer. It will be our second trip as a family to the UK. On our previous trip, we went in December and spent time in London and in the New Forest area. It was a great trip & we are looking forward to going back.

Our current plan in something like this:
London 3 nights
train to York and pick up car
Yorkshire 3 nights, probably staying in Grassington
turn in car, possibly at Darlington, so we don't have to backtrack to York, train to Edinburgh
Edinburgh 3 nights,
pick up car at EDI
Scotland loop 4 nights with the last night in Glasgow before our flight out the next day.

Of course, it would be nice to have more time, but this is what we have to work with in between the kids' summer activities. I have a pretty good idea of how we're going to spend time before Scotland (many thanks to Morgana for her great info on Yorkshire.) What I'd really like is feedback for the loop we are thinking about in Scotland. We hope to see some castles near the route, do some short hikes, and just take in the scenery. We decided not to go too far north, with the idea that we'll be back some day to do northern Scotland and the isle of Skye. I've drawn out a route on a google maps, marking what we think are interesting castles, and sights. I'm not sure how to break up the nights apart from the final evening in Glasgow, and what the roads I have highlighted are really like.

Here's the link to my map:
https://www.google.com/maps/d/edit?mid=zTAPz6w8uhjc.kdLV6aPf3R2g

Really appreciate any feedback and recommendations on where to spend the nights (leaning towards to different locations before Glasgow)

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