I have travelled the road from Skagway over the White Pass to as far as Emerald Lake just east of Carcross, YT, but not as far as Whitehorse. Yep. Very scenic. I have seen mentioned that Haines to Haines Junction is very scenic as well. Haines is a longer route than Skagway. That is the extent that I can comment.
Perhaps mombear will pop in later to advise.
I have done both Philrae, many times.......to me the scenery between Haines and Whitehorse is much better than Skagway to Whitehorse........less traffic and more opportunity to see wildlife, too.......the highway from Haines follows the Chilkat River with glacier capped mountains beyond the river........after you cross the Canadian border you climb a mountain pass with wide open scenery and lakes......stop often along the way to use you binoculars or just to "listen" to the quietude.........there are usually wild flowers along the edges of the road during the summer.......other mandatory stops are Kathleen Lake and Million Dollar Falls, many photo ops along the route.....
On the other hand the scenery between Skagway and Whitehorse has its own kind of beauty......first the highway climbs the steep mountain pass with waterfalls and deep canyons then the road crosses wide open scenery with lakes, very few trees and lots of manmade structures left over from the mining era......this route is more heavily traveled with tour buses and motor homes..........
As Frommy says it is a longer drive from Haines to Whitehorse, but after factoring in the further ferry ride to Skagway it will probably take about the same amount of time (and save you the cost of ferrying your vehicle further)
For me, Haines to Haines Junction is the most scenic section and there is a lot to see and admire including Haines Pass, Million Dollar Falls, Rock Glacier, Kathleen Lake and more.
Both roads are great. Go by one and come back by the other ;) In Whitehorse, there's lots of hotels and restaurants. I like Takhini Hot Springs, 20km from downtown.
Just noticed the "early September" part of your original post........what a gorgeous time of year, the leaves will be showing off their fall colors by then between Haines and Haines Junction !
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