Let's get one thing straight right at the start. There is no bad time to cruise. Whether you want to have a summer vacation or a winter getaway, the weather somewhere in the Caribbean is always warm and welcoming. Meanwhile, Alaskan cruises are seasonal and don't sail the route during the times when you wouldn't want to visit. That said, with our experience having sailed seemingly every month on the calendar, we have found there are definite advantages and disadvantages to sailing each month ...