Italy Itinerary

It looks like a sensible, practical itinerary. You've arranged them in a logical geographic order.

As wonderful as The Last Supper is, I don't think it's worth the time and expense of the side-trip to Milan. Also, think hard about whether you really want to go out of your way down to Amalfi Coast and backtrack to Rome, or whether to save that beautiful area for your next trip. Those days could be tacked on to your Florence and Rome stays and used for day-trips without the hassle of packing/unpacking, checking in/out, etc. But that could just be my bias showing; I like to settle in and get to know a place for a few days. I can't really fault your plan.

$6000 for 15 days is $400 a day. Right now that's 363 € at the best rate. In Rome, even a room in a convent (which can be a very good option) will be at least 90-95 € for two, and a nice boutique hotel can easily eat up the full 363 €. So yeah, I think counting meals, ground transportation, passes, etc., etc., $6K is a minimum, plus your airfare.

Enjoy your trip -- and the planning, which is a lot of the fun.

It will be easier to fly into Milan from Canada directly, rather than into Venice.
This helps you get to see The Last Supper in Milan - it's well worth it believe me.
Day 1: Arrive Milan in the morning - Duomo in the afternoon
Day 2: Last Supper then train to Verona
Day 3: Train to Venice, late afternoon
Day 4: Venice
Day 5: Venice .......
Some hotels to look at ...
Verona http://www.hotel-trieste.it/hotel_verona_index2.asp
Venice http://www.violinodoro.com/
Venice http://www.hotelalcodega.com/
Florence http://www.hoteldeimacchiaioli.com/
Rome http://www.hotelsantamariatrastevere.it/
Rome http://www.innurbecolosseo.it/EN/index.asp

Thanks for the advice! I think I may just skip Milan and and fly into Venice. However, I think I will probably add an extra day to my itinerary and stay in Sorrento day 9-12 and relax then do Rome day 13-15.

Your flight choice will probably be ..
Either Canada to London/Paris/Frankfurt/Amsterdam to Venice
Or Canada to Milan/Rome to Venice

Depending on where in Canada you are flying from, your itinerary could go in either direction. For example, Air Transat's flights out of Venice are generally afternoons (at least the ones I've looked at to T.O.). So the usual warnings about flight times out of Venice may not apply.

You have two days for Verona. That is sufficient to do / see it all by spending one night there. On the other hand, Verona is a short train ride away and just about all the biggies can be done in a day trip from Venice. It will take an early morning start and a late afternoon or early evening return. But, that will save having to change hotels and having to pack and unpack. However, if there are things in Verona that really interest you, then by all means spend a night there.