The glacier landing/dog sledding was a priority for us in 2018. We booked in Seward https://www.sewardhelicopters.com/seward-dog-sled-tours on the morning of our ship's departure. It was overcast, but the cloud ceiling was high enough that we were able to go - the afternoon trips were cancelled. It was an amazing experience! I don't love helicopters, but you're so busy looking at the incredible scenery, that it's really not too bad. And a fairly short flight.
We figured if we couldn't go in Seward due to weather, then we'd try to book in Juneau or Skagway. It turns out that the Juneau excursions were cancelled the day we were there. We feel very lucky that we were able to do this!