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Scotland this summer - some initial planning questions

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We've taken longer than usual to figure out where to travel this summer, but we've decided on Scotland. I know I have a lot of research to do, (I've done some basic reading), but I wonder if you could help me a bit so I can delve further. So, a few questions.
1) When - We've tended to travel May/Jun or Sept. I know there are some big festivals in Edinburgh in particular, and I think I want to avoid those crowds. I also would like warmer weather, so a little later than usual might be better. What about the latter half of June? Is that a good time?

We don't like to flit about, but stay in 4-5 places for 2+ nights each. We like cultural things, and historical things (looks like there are some wonderful castles). We LOVE eating. We look forward to some wonderful hiking, maybe some horseback riding. I also like to stay under 4 hours of driving when we're moving around (and I figure we'll be driving most of this unless it makes sense to train a portion). SO

2) What would be a good itinerary? Edinburgh of course, Glasgow. Isle of Skye seems very intriguing. Is it possible to combine a this trip with some time in the Lake District, Keswick maybe? I don't know much about the various areas, that's what I've been trying to read about mostly.

3) Is the weather better (and by better I mean drier) in any particular area?

4) We're in the Washington DC area - would we do best flying to and from Glasgow? (I guess that depends on itinerary).

Anyway, you can see I'm on the very front end of this. I always like to nail down an itinerary first, snag airfare and THEN start looking for accommodations. Thanks in advance for any help you give.

Alice

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