Sounds like an awesome trip, congrats man.
I lived in London for a year; worked half the time and traveled half the time. General stuff I learned:
Ryanair and Easyjet are an excellent way to travel if you aren't interested in stopping in every town between two destinations. I flew from London to Torino for the Olympics for 40 euro return, after taxes. When you are switching "legs" of your trip, say if you are finishing Nov-Jan in Greece and have to get to the UK, take a Ryanair flight instead of a train.
Jan/Feb in the UK won't be nice. I'd push that into April-ish if it fits with the rest of your trip.
Some places you never mentioned but I wouldn't miss:
Do not miss Switzerland; it was one of the highlights of my trip. Zurich is one of the most beautiful cities I've ever visited. The people there are awesome. Trekking around the old city wall in Luzern was awesome too.
Poland: not exactly a tourist hot spot but it's still one of the cheaper places in Europe. Auschwitz remains one of the most important things I've seen in the world; I've never experienced anything quite like it. You can get a stein of beer and a steak dinner for about $7 CAN in Krakow.
Prague in the Czech Republic was incredible too. Don't order steak unless you like it as it's supposed to be cooked (rare). My girlfriend asked for well-done a couple of times and it's either insulting to the cook or an invitation to be messed with, because in both cases she got the bloodiest slab of meat I've ever seen.
Amsterdam is the best city on the planet (even if you don't smoke weed or buy sex). Nicest people, beautiful city & canal system, awesome nightlife, Riijksmuseum(sp?) and Van Gogh, not as expensive as London/Paris/etc.
London was a blast on New Year's, but Edinburgh looked like more fun.
Hostel prices aren't all that cheap in most places any longer. If you aren't traveling alone, it's often cheaper to split a B&B or hotel room. Go to hostels to meet people, party, and find groups of young people to do tours with. Go to cheap B&Bs or hotels for a cheap place to stay if you can share rooms.
Also, hostels are great for getting recommendations of stuff to do, see, places to stay, eat, etc. Learn from other travelers' mistakes and successes.
The theives in Spain & Italy in particular are scary good. Assume you'll be a target.
IMO, Canadians aren't the universally loved people they might have been 10 years ago. We're nowhere near the level of Americans but you'll run into people that like to push westerners buttons. Bring a lot of common sense with you.
I'll try to think of more later.
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