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Help! Overwhelmed by Italy Trip Planning

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Dear Fodorites,

Please help with planning our first 2 week trip to Northern Italy the last week of May and early June. Last time we went to Italy was early 2000 before they went euro! And we spent the entire 8 days just in Rome. We just booked flights, and I'm reading some guidebooks and already feeling totally overwhelmed by so many wonderful locations and all the complicated sounding logistics--train, museum reservation, etc. Every place sounds so wonderful that I can see spending the entire week just in one location!

Please help plan a nice 1st trip to Northern. We've been dreaming of such a trip for a while, and due to our busy frequent business travels elsewhere in the world, we never made it back to Italy until now. We're husband and wife, physically active, interested in art, architecture, beautiful natural scenery, food, pretty much open to any authentic local experience! :)

Flights:
May 24 (Sun): Land in Milan in the morning
June 6 (Sat): Depart from Venice in the morning
So total only 13 full days

==
Wish List:
Our original wish list was:
* Milan
* Cinque Terre
* Florence
* Padua
* Venice

But now reading up on what each place has to offer and all the wonderful surrounding places, the list above is probaby impossible to do in 2 weeks? Our last trip to Italy, we ended up spending the entire 8 days in Rome because we enjoyed it so much. Should we take out Florence and do it as a separate trip later with Tuscany since, now looking at the map, I realize it's a bit out of the way? Or might as well get a sample of it now, as we don't know how long it'll take us to come back to Italy again.

We want to a nice balance between big places and small places, and don't want a total museum hopping burnout, so mixing in some nature, scenery, or just wandering around town would be nice.

Please suggest how many days in each place and anything else wonderful to see along the way. How about this:
* Milan: 3 days (too long?)
* Cinque Terre: 2 nights/3 days (where to base ourselves, we want some hiking and mix in w train/boat for convenience sake)
* Padua: 1 day trip
* Venice: Well 7 days remaining for Venice which is probably too long. Probably 3-4 days good enough?
* What else?

===
Logistics:

* Train -- so many train options. Given our rough destinations above, does it make sense to buy a Rail Pass? Which one? How?

* Museum Reservations: Please suggest any tips here. Advanced reservation required for the time of the year we're going? (last week of May, and 1st week of June)?

Really realy appreciate any help you Fodorites can provide, and in the meantime, I'll scour your past trip reports. Thank you!

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