Dare I Go?

"Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover."
–Mark Twain

About a week and a half ago my mom put the idea into my head that there's a chance I could be aboard the 72' schooner Dirigo II (Latin for "I direct" or "I lead," pronounced "dee-ri-go") next December as she sails from California to the Chesapeake Bay. The voyage will include going through the Panama Canal, possibly the Galapagos, and I would assume the Caribbean as well.
What a tremendous opportunity to explore and discover things on my own--without mom, dad, sister, or friends along. But quite frankly the thought also scares the crap out of me. Almost every time I think about going--which is often, I tear-up with a) longing to go b) fear that I won't be able to go due to inexperience or finances c) fear of going in general or d) fear that I'll be able to go, but will chicken out and regret it for the rest of my life.
Although I have yet to find a course for my life, my heart is set on this star.