Hi! May is typically quite nice. Most of Southeast Alaska is in a temperate rainforest, so May can be drizzly. But certainly not freezing. Dress in layers, bring a light jacket and you should be fine. I live in Skagway and looked back to photos from May of this year and it was beautiful. I tried to upload some photos to show you, but it keeps giving me an error message. There will not be snow in town, but there will be at the summit and on the pass. So if you do the train, or any type of bus tour going up the highway, there will still be snow on the ground and the air will be cooler. But not winter weather. Just remember you’re coming to Alaska. If you’re expecting hot summer weather, you’re going to be disappointed. But we make up for the cooler summers with spectacular scenery. I think you’ll love it.