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My 50th birthday trip (with teens) to Italy - please critique!

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Hello, I've been hoping to take my children to Italy, just as my parents took me when I was a young teen. Well DD#1 is now 17, and coincidentally it's my 50th birthday -- so although I first thought we should wait til next year (since DH's self-employment status has not yet reached earning status) -- I have decided it's better to seize the moment. Thus, I've been looking at accommodations and think I can put this together in 6 months (fingers crossed for decent airfares!). We are fit, adventurous travelers, although as I type this, I'm wondering if it is too ambitious, especially since we have never driven in outside the U.S. Please tell me if this seems manageable.

-Fly Philadelphia to Venice - arrive a.m.
-Venice - Rialto apartment (3 nts)
>>>Train to Cinque Terre area (6 hours - is this a scenic journey?)
Cinque Terre -- Manarola apartment or Levanto B&B (4 nts)
>>>Rent car (in La Spezia? or train to Florence and rent there?) to drive to Tuscany
-Tuscany -Montepulciano or Pienza (4 nts)
>>>return car to XXX and take train to Rome
-Rome (4 nts)
>>>day trip to Pompeii via train or bustrip
-Fly Rome to Philadelphia

I'm still putting this together, so any thoughts are welcome!!
Thank you!

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