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I think the May 31 would be great! We went the last of May 2 years ago, the weather was fantastic and we spent a week after exploring the Kenai Peninsula. It was relatively warm in the ports, but quite chilly on board. The only drawback is the salmon are not running and we saw only one bear. Glacier Bay was wonderful! Usually the May sailings are a little cheaper than the June ones also.
While weather is highly variable in Alaska and just because it was great last year or the year before is no indication of what it will be like next year. Statistical June is one of Alaska's drier months (again no guarantees) but the real advantage of a mid June date over a May date would be the longer days as you move closer to the June 21st. While I much prefer the period from mid-July to mid-August I would go with a mid June date over a May date.
Do you have specific interests or activities that are a priority for this trip? For instance if bear viewing or fishing are a priority, you need to consider the peak periods for whichever location you're visiting.
... but the real advantage of a mid June date over a May date would be the longer days as you move closer to the June 21st.
In Juneau on May 31st the sun is above the horizon for 17 hours, 46 minutes. On June 14th it's above the horizon for 18 hours, 53 minutes. Either way, even if you don't count almost 3 hours of official twilight, it's shining for longer than I'm up and around.
The end of May can be one of the best times for good weather. The amount of light shouldn’t be a problem. In Juneau the sun sets about 9:45pm the end of May and the middle of June it sets 20 minutes later. In May if you choose an itinerary that includes someplace like Tracy Arm/Sawyer Glaciers or Hubbard Glacier you may have problems getting in very close if there is a late freeze as the ice doesn’t have time to clear the area. Glacier Bay is rarely a problem getting close to glaciers there.