hey man, i was just like you when i was planning my trip in highschool. i wanted to travel forever. the hardest part of it is money and you adressed that by working. so you need a work visa.
lists most of the visas available to canadians and is a good place to check out.
once you got a visa head over there and do a little traveling before you start looking for work. i got 2 months in before i got a job. i had the uk visa and found london to be the easyest place to find a job, but the living costs will get ya stuck there. theres lots of job agencys in london to help you find a specialized position, and the boards work to (try gumtree.com)
i found a job in north scotland serving at a hotel resturaunt in a tiny village in the middle of the highlands, and it was an amazeing experience, one that highlighted my trip.
i ended up comeing back to canada after 5 months in europe, and its not a decision i regret. im a ski bum through and through, and a month or so in the alps just wouldent cut it for me. but even just those 5 months were enough for me to get what i wanted out of the trip, and made me realize i dont need to go across the world to see the beauty of it.
but yea, a good stratagy for you would be to get one of them visas, get a month or 2 under your belt, then settle down and save back some more cash for more travels. the uk visa gives you 2 years in the country with 1 year of work. so you just gotta break that year of work up enough to last you the 2 years. flights anywhere from london are dirt cheap so its easy to get away for a bit.
its pretty cool to get on a plane and think your startin a new life for the next 2 years, and you have no idea whats happening when you get there.