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Help with vacation to Lake District, Milan, Venice

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I'm trying to figure out what itinerary would work best and provide a good deal for the money. My travel dates are flexible, anytime between Mid-September to Mid-October 2015 and would be 8-9 days in the country. This is a mother-daughter trip and we don't mind walking a bit. I'm debating on my arrival and departure destinations. I definitely want to stay a few days in Lake Como. I'm not sure if seeing other areas like Stresa could fit in. The other days would be in Venice/Milan depending on where we fly in/out. We would be flying out from Washington DC.

Here's what I've been thinking:

Arrive Milan - stay 1-2 nights
Take train to Venice stay 3 days
Take train to Lake Como and stay the rest of the days and head to Milan for departure (not sure how reliable train schedules are for flying out)

OR

Fly into Venice stay 3 days
take the train to Lake Como stay 4 days
Train to Milan and stay 2 days and fly out from there

Would you recommend I book flight and hotels at the same time or separate?

Thank you

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