Some say start by setting a date and a destination, then start the planning, the amount of time would then allocate the amount of planning you will do. Then again some say plan out all the details and the date and destination will naturally appear!
If you have the dream of riding to Alaska, then you have already completed step one in my book, you need a strong dream to drive the passion for adventure, most of us that are adventure riders are also big dreamers!
I would suggest setting a date and a ruff idea of the destination see how much time you can set aside for your adventure, then start thinking about how you can make that time match your dream.
Research: asking friends, reading blogs, and surfing the net for information, you will be amazed at the amount of information you can find on the subject its absolutely overwhelming in the vastness of quantity, not nesisaraly quality, you do need a starting point.
Starting point: you need a fairly concise, easy to reference guide as a starting point! I would suggest this is not the adventure forum, not the mile post, not a blog, these are all great places to fill in information gaps and learn form others trips even gain knowledge of what to expect when you are out these, it may also be the fule for your dreem, but not the starting point of you Alaska trip planning.
Books are also a great resource for feeding the dream, but most are just that food for the dream and not a planning guide.
Start your Alaska Adventure ride planning with The Alaska riders Adventure starters kit!
Ok well thats not exactly what its called but thats exactly what it is, and yes it's a book! "The Adventurous Motorcyclist's Guide to Alaska" by Lee Klancher and Phil Freeman. 
now the authers may get a little excited about me calling it a starters kit, but if you think of it like a home brewers starter kit for beer, giving all the right ingredients to make your first "good" beer well then yes this is that for the Alaska adventure. and like any good starters kit, you will want more! And there is plenty of that, this will get you on the right path right now! and In just 221 pages you get a guide to everything form road conditions (ever changing), bikes, gear for the bike and gear for you as well as places to stay and some sites to see.
The advise you receive is well founded and well grounded, from two experienced riders and a native Alaskan, it just doesn't get much better than than!
As you plan your trip keep a watchful eye and the advice you receive don't dismiss the seemingly obvious, as your foundation of planning should be simple, and be wary of the overly complex or costly advice, as your adventure should should always remain well within your means!
You don't need all the latest gear, or bike, but what you do bring will need to serve you well. Better a well tuned Honda Ruckus shooter well within you means than spending your last dime on a shiny new BMW that will break your wallet if it breaks. (Oh and yes I saw more than one Honda ruckus scooter making the trip to Alaska)
Looking at the photoes of the book, it may not be as obvious but the quality of this book is over the top, with think pages, amazing photography and sound advice, it's published by Octane Press and runs about $30, they also have an adventure calendar that keeps me thinking of my next adventure!
The They Sayers, say! Start with the End in mind ? Well, no not really, let's start with adventure in mind and understand that their needs to be room in that plan to just go with it. and that will change many of those well founded plans. Relax, and take some time to ask for directions, even if you know the way!
Also check out Motorcycle Riding in California, my next series of rides, at Ride California or http://ridecalifornia.blogspot.com/
We will ride through the smoke of the yosemite fire,
adventure with a group ride in to the eastern sierras and a ghost town called Bodie !
And explore the back roads and gold towns of California.
http://ridecalifornia.blogspot.com/
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