Sailing with long hair is a pain; plain and simple.
I'm sorry, but these pirates with sexy long hair that we see in movies are doing it wrong. When we did our sailing trip to Kitty Hawk, my hair was far past shoulder length. It was a tangly mess for most of the time and this could be attributed to the hours of being outside in constant winds.
I could combat that a little bit by wearing a hat or pulling it back into a tight ponytail, but when I took my hair tie out to sleep at night, it was still a tangle rat's nest of a mess. This, however, was not nearly as bad as the fact that I couldn't wash it. One thing movies do tend to get right is the smell of a pirate. When you're on the boat for extended periods of time, you just don't shower very often. This is for a combination of reasons ranging from conservation of water and simply not having to because you're not in civilization.
Conserving water is perhaps the most important thing about sailing, so having long hair means that it will get oily and gross very fast, but also that it will take much more water to wash it when you finally do. Therefore, chopping my hair off for this trip was the best decision I could have made. It's easy to maintain, looks great even if I don't brush it, and doesn't whip me in the face every time the wind picks up. It takes about a tenth of the water I used to need to get the shampoo out, and it dries in minutes instead of hours WITHOUT a hairdryer!
Ladies (and dudes), if you were planning to have that sexy surfer look while sailing, I'm sorry to burst your bubble. Everything about those long flowing locks are a giant pain in the butt when you actually get going.