Depends. Whenever you travel, you are taking risks with the weather, anyway. May starts the season, and about late September closes it. You cannot rely on the weather, so be prepared. It could be raining like crazy or it could be calm. Last year, when it was pouring down rain in California (May), it was sunny the whole time we were in Alaska. Go figure. The people said that we had brought good weather with us because Alaska seldom has sun in May. But have a good time, anyway. If you are a shopper, get your deals in May, when the vendors open their shops or in September, when they are preparing to close for the winter. Don't be afraid to name your price!