We just returned from a trip that took us from North Central Florida to So. Cal. Then up the Redwood Highway and Oregon coast to Seattle where we then took a 12 day Holland America cruise / land tour to Alaska. We were planning on driving to Anchorage but opted to make our first Alaska with someone else driving. The cruise started at the airport then a bus to Vancouver where we boarded the ship. Three days on ship to Juneau and Skagway where we boarded a train to Frasier. Then bus to Dawson city where we then flew to Fairbanks. Then bus to Denali where we toured the NP. Then doomed car train to Anchorage where we then flew back to Seattle. We then drove east to Glacier NP and south to Rapid City before we headed east and south to Florida. We spent 105 days on our trip and enjoyed every minute. From what I saw of Alaska roads, I am glad I did not take my truck and FW over them. If I wanted to experience the driving in Alaska, I will fly to Anchorage and rent an RV there.
If you are serious about visiting Sturgis, SD, next year will be the 75th Rally and they are expecting over 500,000 attendees. Get your reservations in early if you are going to be there during the rally.