In Washington state, there is a company called Slow Boat which creates small flotillas and takes them up to Alaska from I think Anacortes into the southern panhandle of Alaska. There are three owners of this company, one of which took his 22 foot express cruiser from Washington into Alaska and back a couple of times.
Here are webinars they have created for folks for the run I have described above. In one webinar, what kind of boat must you have is discussed, the parameters are pretty wide. The longest fuel jump is 85 nautical miles.
Slowboat Webinars – Slowboat