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family of 3 traveling to Great Britain

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Hello seasoned travelers,
My husband, 10 year old daughter and myself will be traveling to Great Britain for the first time. We are arriving at Heathrow early am on the 13th of June and will return home on the 4th of July--a nice 3 weeks. (tickets are purchased)
Our plan so far (all by rail) is to leave London immediately for York for 4 days (flexible), then to Edinburgh (4-5 days), highlands (very loosely defined at this point), Isle of Skye (1-2 days), ride the Jacobite train, see the Lake district (loosely defined), then back to London (4+ days) and fly home to Colorado.
I have a few questions for you all.
1. Does it appear that we need a rail pass for 8 days of travel rather than purchasing each leg individually?
2. I am having difficulty determining an itinerary in Scotland. I don't want to be galavanting around without time to fully appreciate the country, but I also don't want to miss something really worthwhile.
3. Would Edinburgh be an ideal location for day trips once we see the sights in town? I really like the idea of a home base and getting the feel of a town but do want to see the highlands too.
4. Our interests are--me (castles, history, Scotland in general), my husband (anything music related) and my daughter (interesting and fun for a 10 year old).
Any ideas, thoughts, links to other forums would be greatly appreciated.
Michele

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