Itinerary help

WAY too many cities! Too many one-nighters. You're going to see Italy from a train looking out of a window! Every single time you change cities, even with a shorter train ride involved, it eats up almost the entire day! Think about it, you repack, check out of the hotel, take transportation to the train (or airport), ride -- then taxi to the next hotel, check in........... Unfortunately we're not yet advanced enough transportation-wise to be "beamed up," i.e., Star Trek.

While I absolutely Adore Paris, I'd skip it this trip and save it for next time. That will save you two trips through airport/security, etc., which will really waste your whole day! Vacation time is MONEY and you're spending yours at airports and train statioins

Take another look at your travel guides and do an honest evaluation of what is Most Important to you and spend a minimum of three nights in each locatioin with the possibile exception of Venice, which you can "do" with two nights sleeping there.

Florence needs at least two full days (three nights), and an additional night if you're planning day trips.. The way you are scheduled now, with two nights in Florence and one of them a day trip to Chianti, you've basically got a few hours to spend in Florence!

Depending on the time of year, I'd either completely skp Cinque Tere (if it's early spring or late fall) or Lake Maggiori and just focus on Florence, Venice and ONE of the remaining towns which interests you most.

Ok so I updated my sedule a bit..
Sept 3: Arrive in Milan, sleep in Provinciale 38 Vogonga (vb)
Sept 4: Milan to Lake Maggiore, sleep in Provinciale 38 Vogonga (vb)
Sept 5: To Verona Sleep in Verona
Sept 6: To Venice, sleep in Venice
Sept 7: To Venice, sleep in Venice
Sept 8: To Florence, sleep in Forence
Sept 9: To Florence, sleep in Florence
Sept 10: To Chianti, sleep in Florence
Sept 11: To Florence, sleep in Bevagna
Sept 12: To Bevagna, sleep in Bevagna
Sept 13: To Bevagna, sleep in Paris
Sept 14: To Paris, sleep in Paris
Sept 15: To Versailles, sleep in Paris
Sept 16: To Paris, sleep in Milan
Sept 17: To Milan and, sleep in USA

Are you thinking of flying to and from Paris? That would be better than 14 hours on a train from Perugia, but getting from Bevagna to Florence or Pisa airport also takes 2-3 hours driving time, plus check-in, hence Donna's concern. Is the return flight from Milan already purchased or would you have the option to fly home from Paris?

That looks do-able! I'm just curious about Paris being on the schedule in this way? If you could fly INTO Paris and fly out of Milan --
or the other way around, you'd add a full day to your trip! If your r/t tickets are already purchased into and out of Milan, well, then that's that! I still think you should devote the entire trip to Italy and save France for another day -- but you'll have a wonderful time!! Have Fun!

My general rule is to divide the number of nights available (14 in your case) by 3 to get the possible number of destinations. So I would limit myself to 5 or 6 places if I was you ...
Italian Lakes (2 or 3) - Verona (1) - Venice (3) - Florence (4) - Cinque Terre (2) - Milan (1 or 2)
Or if Paris is indispensable ...
Paris (3) - Italian Lakes (2) - Venice (3) - Florence (3) - Cinque Terre (2) - Milan (1)

I'm confused why Paris is on this itinerary. I'd save that for another time and take the above itinerary and add the 3 days in Paris to Venice or Florence or even take a couple days in the Tuscan countryside.