For planning I advise folks to decide why they want to go to Alaska and northern Canada. If photos of baby wildlife are important, then go early in the summer. If fishing is important, look up the historical data on when the salmon runs occur, I like to print out a calendar for the months I plan to be gone and start filling out where I want to be and when. If I plan to fish for pinks in PWS, Valdez area, then I know I need to be there a couple of weeks after the 4th of July. Often if I am in a fishing mood, I will fish the Reds on the Russian River on the Kenai, then head over to Valdez. So by the time I get everything I want to do plugged into the calendar, most of the trip is planned.
We tend to spend about 3 nights in Whitehorse both directions, will visit, on about a three trip schedule, Skagway, Atlin and Dawson Town, one of them each trip north.
I also pick a general theme for my photography each trip. By viewing the past photos on my computer, I can get an idea of what I am missing either by loss or a change in my interests. One trip it was old roadhouses, one year out houses, airports, campgrounds, etc.
plug in the dates of special events you want to attend, such as one of the state fairs, musical events, sports games,
Once done with the calendar, I start moving things around so we are not running back and forth across the state. We find out when friends we want to visit are going to be home to work those dates in. The plan always seems to get changed by the time we get there. On a two or three month trip, I know I am going to have to pay bills each month which I do electronically. So on the bill paying dates, I need good cell service or secure wifi. Most trips I use Whitehorse, Fairbanks, Valdez, Anchorage or Homer for bill paying. So far, have never had a problem.