So I've been working on a trip to Europe for some time now, but I feel like I can really use the help of a few more experienced people since this is my first time doing so. I'm planning on visiting 16 cities (10 countries) over a 43 day period, with most of the traveling between cities being done overnight. What I'm trying to decide on is how many days I should spend in each city and if I should eliminate any cities in order to extend my stay in other cities. I'm using days not nights, since it makes more sense to me. This is my plan so far, in order of cities I'll be visiting:

Fly from Toronto to Lisbon
Lisbon - 3 days
Madrid - 3 days
Barcelona - 3 days
Nice - 1 day (just as a stop over on the way to Milan)
Milan - 2 days (maybe a day trip to Genoa)
Florence - 3 days (and Pisa)
Rome - 4 days (and Vatican city)
Venice - 2 days
Budapest - 3 days
Vienna - 3 days
Prague - 3 days
Berlin - 3 days
Amsterdam - 2 days
Brussels - 2 days
Paris - 4 days
Fly from Paris to Porto
Porto - 2 days
Bus from Porto to Lisbon and fly to Toronto

So what are your thoughts on this plan? If I had to prioritize my trip, I'd say Brussels, Amsterdam and Berlin are probably cities I can skip on, though I'd like to see Berlin as well.

Thanks in advance.

Others can talk about their favorite cities, but you have far too few days for Paris, and not enough for Amsterdam or Venice.

Part of the fun (call it what you like) of a trip is to get out of a city and see what the local folks are like.

Your trip sounds like one of my mother's tour groups she goes on "we saw everything, sort of".

In the period of time you've got, pretty soon every city will begin to seem like a blur.

Seeing less is often seeing more. Cut down your itinerary by half.

All this overnight travel... have you actually checked on train schedules? It doesn't take overnight to travel between many of your planned cities.... Amsterdam-Brussels is a couple of hours. Ditto Brussels-Paris.

But by the time you check out of your accommodation, get to the station, buy a ticket (lines can be long, take the trip, find your accommodation in the next city you've expended a lot of energy and time. ;^(

I'd strip out Milan and Nice as well as Brussels that frees up 5 days, I'd think about Porto as well as it doesn't really dit well with the other cities. I'd try and get an open jaw flight to go back to Toronto from Paris.

Now please tell me you are not doing this in July and August?

Less is more.

Most people on this forum prefer a slower approach, so that is the feedback you are going to get. You really just need to think about what you want out of this trip--if you want a grand overview of western European cities, then I don't see any glaring problems.
I have to say this would wear me out, but I am 39, and that is just my personality. When I did my backpacking trip, it was woefully short and I loved the overnight trains, but you can expect to need some r&r at some point. If I was going to critique, I'd say try to build some of that in.
My other critique would be that it is all cities, but again if you are looking for that grand overview, then it is also probably easier to get from place to place without adding in rural areas or small towns.
have a great trip!

Actually, planning a trip in terms of days, rather than nights, isn't the best way to get a real sense of what it will be like, because after you figure in the packing up time, getting to the station time, train time, getting oriented time, finding your accommodations time, unpacking time, getting a bite to eat time, etc., well....there goes the day.

Just to clarify, I found a very good deal on a flight, so I have already booked my flight from Toronto to Lisbon on April 30th, and from Lisbon to Toronto on June 13th.

My plan with this trip is to do a "must see" sight seeing tour of Europe. I want to see all of the major places but still have enough time to walk around town and see a few local places as well (specially in Italy).

As for the night trips, I looked into trains but it was out of my budget. Instead I plan on taking buses. I found night bus trips between most cities. On the longer trips I plan on just sleeping on the bus (like from Venice to Budapest) while for the shorter trips I'll take early morning buses instead.

I highly recommend you post on Lonely PLanet's Thorntree chat board as many posters there will be doing backpacking trips - where most people here will not.