..... I am however going to invest in a few vests. I'm looking at the Switlick for the boat since space and getting off the boat is less limited. For future flying I'm considering the mesh vest I was linked to over an inflatable.
As for the pistol I had considered a Taurus .44 magnum or a .454 Casull magnum ......
You haven't said much about your itinary, or how you will be traveling to Alaska. If you are coming by boat, you will presumably be going up the Inside Passage through Canadian waters. If by auto you will be driving up the Alcan. If either is the case, you definately need to check into Canadian regulations regarding firearms. Handguns in particular are highly restricted in Canada. Way back in the day, people tell me that the Canadian Customs agent would just seal your 44 when you entered Canada, and as long as the seal wasn't broken while passing through Canada there was no problem. In more recent years this has changed, and my understanding is that these days, getting a permit to transport your handgun through Canada is a major hassle. More than a few Alaskan pilots have gotten themselves into trouble with their survival pistol while flying to or from Alaska. I think most long guns are not such a big problem.
Best to check well in advance with the Canadian authorities about the necessary paperwork. If you do not have your permits in order, you risk getting the gun confiscated, and prosecution. Obviously if you are not driving or sailing up this isn't an issue.