If my hubby would fly, I would definitely go by plane next time. Cruising around the islands is very nice - waking up each morning in a different port. It was just the days getting there and coming back. DH actually said he would fly back but that's not a possibility with that "Jones Act". All kinds of penalties and such. And he doesn't even like to say the word "fly"! Keep in mind that everyone has their preferences. You might enjoy the sea days. Also, I had read some bad reviews of the NCL ship that cruises the islands. Hope I didn't confuse you even more, but it's all a matter of opinion. If you've never been there it might be nice to cruise the first time. That way you get to see all the islands. Unfortunately, our Maui stop was cancelled due to weather. Then, when you go back you know where you want to go and can fly over to that island.
Let me know if you have any other questions.