Skagway - train, jeep or car?
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but my DH really likes trains.This would be how I'd base my answer, historic train...
His parents enjoyed the train but they said it was boring coming back since the view is the exact same in both directions. They were jealous they didn't come with us in the car.
If you do drive, be aware that gas is hard to find so fill up when you can, and also be sure to take snacks / drinks with you in the car. There were long stretches on the road where there was nothing but nature. I don't know where you'd plan to drive, but our route was absolutely beautiful.
If you rent a car the driver will be so busy driving the curving roads that they will not get to enjoy the trip. So I suggest you have your parents do the train/bus trip and you do what I did on my third trip, I went with my husband and used the small tour buses that went up and back. This was very nice as not as much time was used loading and unloading those who wanted to take pictures. We made more stops and the guide/driver was a local who had great information. I got the bus right where the ship docked, it was half the price of the ships bus trip.
Have a great time!
There's also tour operators (Dyea Dave comes to mind) that offer trips that combine driving and one-way train passage.
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Here's what I did: I rented a minivan from Sourdough, and hired a guide from Dyea Dave. This combo allowed me to go all the way to Emerald Lake and back, and drive to the start of Chilkoot Trail and back, and see Dyea, the Skagway overlook, etc. And the total cost is perhaps 2/3 or 1/2 or total cost if my family did the same whole itineraries as bus trips.
The next time (I had my grown daughter who's also a mountain climber) I rented a car BUT it was so foggy, we got about four miles up the hiway and turned around to return the car. There was no way we'd see anything, plus I didn't want to get run into.
So, the road AND the train were both deep in fog...........a waste of money for THAT schedule (early morning.
Once I rented a car because I knew my SIL would complain about the hard benches on the train............our drive was heavenly. We took snacks so we could have "lunch" by lakes, etc. and noticed, for instance, that places to stop for ice-cream, etc. had long lines because tour buses often stop at those places.
If it's to be your one and only time to Skagway, I'd suggest the train because it's a once in a lifetime experience!
Sunny days to you!