Not too far from where I live, there is a small lake that offers kayaking on an hourly basis. I love the water and though I don't long to sail, kayaking was really fun. The day we went, it was a summer evening, warm, and it was just getting dark when we returned from our tour of the lake. I can't wait to take Mason now that he is big and old enough to captain his own kayak! Finding things to do that are similar to the main idea will acclimate you to so many nuances of the general field -- in this case, boating.
I realize that one may have to make some major changes in their life to make a dream come true, and relocating could be an option. Orange Roads don't make it easier or less expensive to make your dream come true, but they are avenues. The trick is to see them as adventures and not obstacles!