Looking for Advice in Italy

If you've never been to Paris, obviously I would stop there on the way to Nice. Easy to get there by train.

From Nice, maybe head toward Milan and fly out of here. You could check the logistics/price of flying out of Bologna but I'd guess Milan has better connections out. You might also consider flying out of Venice - sometimes you can get better flights out. You need not stay in Venice the night before depending on how late your flight out would leave. There are some small towns near Venice like Padua or Verona that might be nice to visit for a final night - then just taken an early train to Venice Mestre and an express bus from there to the airport. I'd only fly out of Venice if you find much better times/prices for flights than flying out of Milan or Bologna.

Otherwise, figure out of the places you mention what you want to see and plot a course back on a Google map. All very easy to do by train.

You might consider a stop in Turin on the way over to Milan - nice town too. Really depends how much time you want to spend in these other places.

Great advice, thank you so much!! Any ideas on a good area to stay in Paris? Maybe somewhere quite central to walk to resturants etc?

It looks to me like you're trying to fill two gaps in your itinerary, May 17-21 and May 26-31. If you don't already have your transatlantic flights booked, is there a reason to fly home from northern Italy rather than Paris?

I'd suggest Paris for one of the gaps and Milan + Lake Como for the other. If you do Amsterdam-Paris-Nice-Milan you could do it all by train. If you do Amsterdam-Milan-Nice-Paris then you'd probably want to fly from Amsterdam to Milan (avoiding those pesky Alps that will slow you down on the ground). Check out the options on Rome2rio.com (but do your bookings with the actual carriers).

Another thought -- Just because you've been someplace doesn't mean you can't or shouldn't return, to see more or repeat something you especially enjoyed or see how things have changed. But, that said, if you haven't been to Paris you should definitely check it out. (In fact, you might consider Paris for both of your gap periods.)

EDIT -- You also asked about places to stay etc. in Paris. If you decide to go there, post questions on the "France" forum to get a lot more answers.

Where are you flying home from? Also you said 3 days in Amsterdam but I only see 3 nights, the travel day is kinda lost because of jet lag. Any day you change cities you lose half the day. So for 3 full days you need 4 nights. Seems like Amsterdam-Paris-Nice- then 5 nights for Italy.

Thank you all! I was able to find one way tickets from AlaskaAir for PDX to AMS for 45,000 miles and $188. which is fantastic (hopefully) but I can't find a return trip to Portland that doesn't take less than 30 hours and two very long layovers..any advice there would be so helpful, I feel like it's getting down to the wire booking a flight.