3 week itinerary- Please help review before I book! Italy Portugal Amster.

It's kind of only personal opinion, but I like my sites to be closer together when I travel. You are moving around quite a bit, but if you're experienced at European travel, and don't mind all the travel time, then ok. Also, I love Bologna, but if it's your first time to Rome or Venice, I'd give that time to those two cities and skip Bologna this time. And if you're already in Bologna, why not try to fly from Bologna or Venice to Lisbon, rather than going all the way to Milan.

As noted, its personal tastes here, but Amsterdam and Venice do not deserve more time then Rome.. Rome has so much to see and do,, I would take a night from Amsterdam and give it to Rome. I would sit down with a guide book and list what sites you would want to see in Amsterdam,, and what sites you would want to see in Rome,, think you might find the list longer in Rome. Venice is nice,, its pretty, its romantic,, but its also very expensive, and for me personally ,, its a two nighter( expcept perhaps for those on a honeymoon?) anyways, its all personal tastes as I said,, so you will likley get lots of different views.

Thanks for the replies, it really helps trying to think through this I am a little concerned about the 2 flights w/in Europe. This will be my second trip. Last time I did 1 flight but visited Italy, France, Amsterdam, Barcelona, Munich, and Brussels....so way too much moving around! These are the places I really want to go though and the flights seem cheap and quick. Is there a flight from Venice or Bologna to Lisbon? Milan was the most direct I could find.
I figure I have three pretty full days in Venice since I can leave later for Bologna the last day. My mom will be with me the 1st 7 nights. This will be her only trip to Europe and she really wants Rome and Venice. Flying into Rome so no way to extend that portion, unfortunately. Otherwise I would have 1-2 more nights here.

Can you fly into Faro instead of Lisbon...and then out of Lisbon to Amsterdam? It's at least a 3 hour jaunt from Lisbon to Lagos. Then, you'd have only about an hour jaunt to Lagos. (I personally really, really liked Salema, and stayed there for 3 nights. I also REALLY liked Lisbon. I'm jealous.) I would probably skip the 1 night in Orvietto, personally, just so that I didn't have to pack/unpack again. Add another night in Rome! :-)

For my taste, I find your itinerary very disjointed. Why create an itinerary that requires so much inter-country air travel? There's no shame in planning a trip around one or two key areas, such as Itally and southern Germany or France - why Portugal of all places? and then a trip way north to Amsterdam - these are all honorable places and goals but you've created a trip that's going to be a lot of work. I think Rome and Venice are worth more time, as well.