Skagwayhas Continental Mediterranean type of climate throughout the year. Therefore, you can visit the place any time of the year according to your schedule. In general, summers and autumns are the best time to visit Skagway. During this time Skagway has clear sky and pleasant days. Peak tourist season is mid-May to mid-September.
Winter months could turn a little too cold for comfort. Therefore, if you are not too comfortable about freezing weathers, it is better to avoid Skagway.