Though it is possible to do a cherry blossom trip on your own, if you want to see multiple sites and get more out of the trip, I’d suggest a tour. It is much easier to navigate in these rural areas that off the English speaking tourist path when you have a guide. Though Japanese people tend to be helpful if you need directions, a tour will really help you understand the intricacies. I always like to ask questions and hear more background about each location. You can research itineraries based on locations, length of time and other included experiences.