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Northern Italy/Switzerland mid May??

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I booked a great fare from JFK to Milan in mid May ($799 for 2).We will have 14 days on the ground, not counting arrival/departure days.

We are interested in: outdoors; walks or easy to moderate hikes, food and just soaking in the beauty. We are ok with train or driving.

First - input on weather this time of year?? While I know the unpredictable nature of weather, just wondering if we might have some dry weather this time of year? Warm would be nice, but at altitude, know that is less likely.

Fodors has what looks like a nice itinerary - http://www.fodors.com/world/europe/itineraries/northern-italy-and-switzerland-the-lakes-to-the-mountains-44/

If we do something like that, we'd have to fly from Zurich to MXP, air fare is about $100. Thinking if we drove, there might be a big drop off fee.

Any input into how we could best use the 14 days and perhaps not have to fly from Zurich would be appreciated.

We would be willing to do less stays to lengthen number of night per place or we can keep it to short stays in each spot. I know how much time you lose transferring, but perhaps 2 or 3 night per stop in this kind of itinerary is better.

This really just fell into my lap today, wasn't on the radar and have 24 hours to keep it tickets or not.

Thanks in advance~~

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