Keeping in mind I've only done one trip to Montague -- a boat based hunt in November 2003.
- A sunny day on Montague...rare?
Be sure to start with a good map or two. There's a lot of public land, but there's some private/native too. Personally, I'd steer clear of the cabins...because lots of folks have already hunted there. If the snow hasn't forced the deer down...be prepared to hike up to them.
Don't forget a shotgun if sea ducks are in season. I took a beautiful double-banded Harlequin there too.
Gotta run and catch my plane in a few hours...off to Valdez for black bear. Man, I miss Alaska.
When to go would depend on what you want to get out of the hunt. If you want prime deer to eat, I like early to mid Oct. If you want to hunt the rut for better chances at a nice buck, early to mid Nov. is best. If you want to see the most deer with the least work, late Nov. through Dec. is usually best depending on snowfall of course. After a good snow, the deer will pack the areas close to the beaches. But if you don't have a boat of some kind to get around in, the snow can cause it's own problems for you. If you don't happen to pick a spot they migrated to, you may be fighting the deep snow to get to where the deer are. Also, hunting in knee deep snow is an art and takes some getting used to.
And then there's the weather. While it can blow here on the Sound anytime of the year, generally the later you wait to go, the more bad weather you'll get. Take that in to consideration while planning your hunt. Allow extra time to get out to hunt and to get picked up. It's best if you're not pressed to get back on a certain date. As an example, in early Dec. last year, I met two groups of hunters who had just made it back to Cordova. One group was a couple guys from the Valley who had tent camped on Montague. The other group was at least 4 guys from Anchorage I believe and they had been camped in a cabin on Hinchinbrook. Both groups were a week late returning because the weather had turned so bad their planes couldn't pick them up safely. The two guys on Montague had limited out if I remember right, and the guys on Hinchinbrook had gotten a couple deer apiece. But I think their time in the storm might have been a little nicer in the cabin than the guys in the tent. I know all any of them wanted was a bath. And another problem the guys from Montague mentioned was that their deer were getting a little funky. When they started hunting it was cold with snow. Then it warmed up and rained and blew so the meat didn't keep as good as they'd have liked.
Sometimes getting dropped off by boat is better than by plane if you have a rigid time schedule. If you talk it over with the Capt. he can let you know areas where he can pick you up even if the weather is bad. It might not be a fun boat ride, but at least you can be picked up. Another thing to consider is generally you can take more gear on a boat and get your deer back without having to pay for an extra trip as happens with planes sometimes. Not trying to discourage you, just pointing out a few things to consider.
All in all, if it was me, I prefer Oct., but you may have other priorities than I do. Here's a pic from an early Dec. hunt on Hinchinbrook last year. Good Hunting!
I recall a message posted a few years ago that the Beach River cabin area was a "meat harvest" for a deer trip in December. Alot of deer. I think they went around christmas, and reserved the cabin the maximum time in advance, 6 months (right around now).