Itinerary input please!

Just curious - why are you going to Amsterdam for one night just to fly home? Why not just fly home from Paris?

Home is Toronto, and a number of the flights have a stopover in Amsterdam anyway, so I thought we should enjoy it :)

If that's the case I would take 1 day from Siena (just spend 1 night there) and add another day to Amsterdam. Siena is often done as a day trip from Rome and that's enough for most people. I'm sure you'll get differing opinions and, don't get me wrong, I liked Siena - we spent a night there - but you'll get so much 'Italy' that it would be nice to mix it up a little as long as you're going to fly out of Amsterdam anyway.

Oh, this looks like such a nice trip! If this were my trip I'd cut Pisa and Siena entirely, add a day to Rome and have at least two full days in Amsterdam.

This is a great itinerary. I would visit Pisa as just a stop over for lunch on the way to the Cinque Terre. You could add the day you save to Amsterdam. Other than that, I wouldn't change a thing. I would not skip Siena.

I don't share Nancy's views on Siena. I think it is worth at least two nights. There is much to see there, and it is a wonderful place to stay just for the ambience. Evenings in Siena are wonderful, after the day-trippers have left. I would subtract the night in Pisa. If you really want to see the tower, you can stop there on the way from Florence to CT, take a few hours to see it, and then move on.

I think four nights in CT is more than you need, but if you are confident you can fill the time with swimming/snorkeling/diving/hiking (keeping in mind that in May you might or might not have warm swimming weather), that's fine.

However, you should know that if you are Da Vinci fans, you won't find that much of his work on this itinerary. Florence was Michelangelo's town; I think there are maybe 3 works of Leonardo at the Uffizi in Florence. His greatest work, The Last Supper, is in Milan. (Of course, there aren't that many extant works of Leonardo anywhere.)

This is really an Italy trip. If you need to go to Amsterdam to fly home, why not just spend the last few nights there and skip Paris. Then you might be able to add some time in Milan. Paris will still be there next time. But if you can figure a way to fly home from Milan, I would just spend the entire trip in Italy.

Paris has several of Leonardo's works, as does Milano. There are a couple of pieces in the Vatican, and several in Firenze (mostly in the Uffizi). There are a few Leonardo museums in Italy, too.You could make a side trip to Vinci.

I like the overall pace of this itinerary a lot, but I agree that not having some real time in Amsterdam is a shame.

I'd do something about the three different hostel stops in Florence/Siena/Pisa. They are so close together, and there's going to be time wasted packing, checking out, checking in, etc.--though perhaps not as much time as when staying in hotels. Pisa can definitely be done as a stop-over or day-trip.

I am a big fan of Cinque Terre, having been there three times, but I'd definitely steal a day from C.T. to use elsewhere. In the first part of May, I'm not sure how certain you can be of swimming weather, and even heavy-duty hiking could possibly be rained out. As Canadians, no doubt your tolerance for chilly swimming conditions is pretty high, but still...Would it be possible to keep that part of your itinerary flexible until you can see weather projections? Bologna would be a decent place to run on a really rainy day, because most of the streets in the huge historic district are arcaded.

Just 3 days in Rome, one of them being your jet-lag day, is rather short. I'm having a hard time deciding what I'd do with one extra day--add it to Rome or to Amsterdam?

I had planned the Pisa as a half day, no overnight there. I too am waffling about only one day in Amsterdam.
I know when I traveled last, I hated the one night only stops, so was only wanting to do the one, just before heading home.

You have 19 nights. Make Amsterdam more insightful by scheduling Pisa and Siena as day trips from Florence.

Rome - 3 nights
Florence - 4 nights
Cinque Terre - 2 or 3 nights
Venice - 2 or 3 nights
Paris - 4 nights
Amsterdam - 3 nights

I guess I still don't get it about Amsterdam. Are there no good flight connections between Paris and Toronto, so you have to go to Amsterdam to get home without too much trouble? Otherwise, you're giving up a day or part-day in Paris just to ride on the Thalys ($$$ for four of you) to spend one night in Amsterdam and, presumably, fly home the next morning. I'd give that time to Paris. Or, as others suggested, shorten up the Italy time and shift it to Amsterdam at the end, so you don't "under-do" that city.

But don't go snorkeling in the canals! Too many motorboats. ;-)

How about Rome > CT > Pisa/Siena > Florence > Venice? There's less backtracking. You can check bags at the Pisa Centrali station for 1/2 day to see the Field of Miracles (and Tower) then continue to Siena. Even with eliminating the overnight in Pisa, you still have a lot of hotel changes. Bear in mind that 4 people will only move as fast as the slowest one at any given time. That's getting up in the morning, packing, breakfast, etc. etc. Also some hostels require you to be out of the rooms for several hours from mid-morning to mid-afternoon, so be sure to check that there will be a place to leave luggage if you plan on arriving then.

Don't expect warm water. The temperature of the water on our coast today is 22 C. and we've had a couple weeks of full sunshine and unseasonably warm weather (high 20's and into the 30's). We're much farther south than the CT and with long stretches of sandy beaches and shallow water, so different from the CT coastline.

I have been to all these places, most more than once. It works for me, but i would do fewer days in cinque terre. If you want to snorkel, go to the Caribbean or Great Barrier Reef. Also, two days in Venice is probably enough. Three days in Rome is not enough.