As usual, I'll chime in with Italy advice... Do it in the spring. The weather is perfect. Not too hot, not too cold. Sunshiny.
Winter sucks in Italy. Since most of it is coastal, it's Vancouver all winter. Rain, rain and more rain. And then more rain. Every day, rain. From mid november to mid march, rain. And dacember and january are particularly miserable because the temp gets down to 5 degrees, which feels really damn cold when it's so humid and rainy.
But spring in Italy is amazing. The sun comes out in early march and the temperature suddnly shoots up to daily highs in the 20s and then into april and may it's high 20s, then june, july and aug will be in the 30s daily.
I highly recommend staying at hostels. Bounce around for the first few nights you're in a new city and find a hostel that will give you cheap long term rates. You'll learn to travel light and you'll discover that when your life revolves around work, exploration and meeting new people, you really don't need 'stuff'. An ipod, a cheap, losable cellphone, a small camera that you vigilantly upload your pics to a place like photobucket or whatever to store your pics in case your camera gets stolen... Really, for a trip like you're planning, your only precious item should be your passport.
All your clothes should fit into one checkable bag and one carry on bag. I did it with a traveling backpack and a regular backpack, but I was a bit jealous of the people that spent more money and got badass suitcases that clip together and have handles and wheels. On the other hand, alot of european cities have really uneven cobblestone sidewalks that will destroy those wheels pretty quick. For you, a travel backpack might be the better way to go.
Just don't forget to travel light. Clothes are disposable. You'll wear them out and buy new ones. Shoes are important. Save money on clothes and spend it on good shoes.
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