Skyline Drive seems like a great idea, and it's nice for the fist few miles, but the speed limit is 35 and you are always behind an RV going 15. After pulling over a few times and taking a few photos, you are ready to pick up the pace. And there are no conveniences for many, many miles, so buy an iced tea and jerky before you enter the park.
I did it on the old CX500 a few years back. Damn, now I miss the old girl.
I went down Skyline mid week in mid August, missed most of the RV crowd and didn't seem to notice the speed limit signs much either. 
It and the first hundred miles of the Blue Ridge Parkway are great however.
2 weeks isn't enough time to ride to AK from most of the lower 48 and actually get anything out of it. Maybe fly to Anchorage and renting a bike from MotoQuest. A GSA is completely unnecessary but very competent for the ride, I'd prefer a G650 or an F800 for a lighter bike on the mud and calcium chloride they slather on the Dalton.
From Anchorage, ride north on the Parks Highway to Fairbanks (1 day), then north on the Steese and Elliot Highways to the Dalton, up to the circle and back can be a day trip. Up to Deadhorse is at least two days but better ridden in 3.
It's another days ride from Fairbanks to Dawson in the Yukon, which is worth the trip imo. Stay a day, then ride back to Tok and turn down the Tok Cutoff And eventually down to Valdez. From Valdez ride back to GlennAllen and ride back to Anchorage on the Glenn. If you have time, take the day+ ride down to Homer at the end of the Kenai peninsula. Then fly home. Only gravel is the Top of the World Highway to Dawson and what you choose to ride on the Dalton, so any street bike will work.
In reply to skierd:
Thank you for this. It's always good to hear from a local
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