The Sailboat Dream

There is, unarguably, something about sailboats that resonates in the hearts of dreamers. If you’re reading this, no doubt you are a sailor, a dreamer, or both. Welcome, brothers and sisters of my tribe! Let me describe some possibilities for your voyage.

There are about as many variations of the dream as there are sailors and someday-sailors. The common element, though, is the idea that a sailboat is the perfect vehicle, the only vehicle, for taking you to a better lifestyle, a lifestyle that will satisfy what is probably an unarticulated but important emotional or even spiritual need. Whether weekend sailing with the kids on a little lake, a one-shot, bucket-list cruise through the Caribbean, or an open-ended cruise around the world, all differences aside, all boat dreams sprout from hopes of a better life, however you might define “better.” Nobody, but nobody, becomes a sailor because it is convenient.

Outer voyages require only a boat, a significant body of water, a desire to travel by boat over the water (i.e., the hard but fun way), and a desire for adventure. Adventure is never what one expects: that’s the rule. It your outer voyage turns out to be mostly what you expect, what you’ve dreamed of, well, you’ve had a trip, a vacation. For it to be an adventure, at some point during it you must at least once ask yourself at least one of these questions: What the hell do I do now? Why in hell did I get myself into this? How in hell am I going to get myself out of this? Oh my God, what a wonderful life I live – when can I do this again? (The more of these questions you ask yourself, and the more intensity with which you ask, the better the adventure. Hey, I didn’t make the rules; I just write them down.) (Note: an optional question is, Am I even going to survive this?)

Inner voyages are a bit trickier. For now, I’ll give you just three quick thoughts, to be expanded upon later. First, from George Bernard Shaw: “Men are wise in proportion not to their experience, but to their capacity for experience.” Second, that rule about adventures never being what you expect them to be? An inner voyage is always an adventure. Why? Because unlike in the old-time stories of the sea, the dragons and serpents and demons of inner voyages are very real. Third, surprisingly, the inner voyage has very little to do with achieved expectations of the outer voyage. More on all of this later; for now, let’s get started.

I’m not going to tell you how to repair or rebuild a boat: there are plenty of books to do that, and plenty of authors much more qualified than I am. (I will, though, give you a few pointers from things I learned the hard way, helpful tips I don’t remember coming across in other sources.) For anyone contemplating getting a used boat and rebuilding it, what I mostly aim to do here is give you a feel for the process, give you some (second-hand) experience at bringing a used boat back to life.

First: The trick to finding and buying a good ol’ boat for a great price.