Flying to Alaska can be easy, but I would not recommend it for an inexperienced pilot. An instrument rating (which I had and did not use on the entire trip) is almost useless, as the MEA's are typically in icing year round. A hand held GPS, or a panel mount, made our trip relaxing instead of challenging, and navigation was done almost entirely by dead reckoning and GPS rather than use of navaids. Loran C does not work much above the US border, but according to an Alaskan pilot if you have a later unit with the 7960 chain "X" secondary receive capability it generally works along the Alaskan coast below the Arctic circle, but doesn't work well in the interior routes through Canada.
Transitioning through Canada is similar to US flying, with some exceptions. Flight plans are required for all cross-country flights, and minimum altitudes are 1000 feet. Crossing the border also requires customs notification and, of course, a flight plan filing. Depending on your route of flight, fuel availability can be an issue, so stopping for fuel more often than usual makes sense. Fortunately, during the long days in the summer time, FBO's remain open late.
There realistically are only two main ways to get to Alaska from the lower 48 states. One is to fly to Dawson Creek and fly along the Alaska Highway to Tok, Alaska, where you clear customs. You can pick your valley from there, flying to Fairbanks or going south towards Anchorage. The second way is to fly "the Trench" along Lake Williston in BC, which also joins the Alaska Highway in Watson Lake. At the time we flew that route on our return, fuel availability was 450 miles apart. The third option really isn't one, that is flying along the coast. There is very little shoreline available for an emergency landing, and I'm told that even floatplanes are risky on this route because of the likelihood of being washed into the rocks by the surf. Another inland route exists from Prince George to Watson Lake via Dease Lake. You can fly from the US to Anchorage, Fairbanks, and most other cities and towns without ever having to fly any higher than about 3500 feet MSL, and that happens on the Alaska Highway in the Yukon (where you can by-pass the highest point on the highway by flying through an adjacent valley). Our highest obstacle getting there was crossing the Adirondacks, right near home.
We always filed a flight plan in Alaska, and the typical route would simply state the name of the river or the highway we would plan to follow to our destination. Flight Service personnel were pleasant and extremely helpful in Alaska and Canada, but weather changes quickly and so should flight plans. Much of the flying is done beneath low ceilings with good visibility, but we always tried to have several other options (including returning back to the departure point) besides the destination.
There are a number of other useful resources available if you are planning a trip. I haven't published them here, but if you are interested, contact me and I'll try to fill you in.