Buying A Boat and Learning To Sail: Part I

Last Wednesday we took a trip over to Bloomington, IL to check out a used Walker Bay 8’ dingy that we saw on Craigslist. We decided to look at the boat after we had a discussion about me wanting to learn how to sail. While I am gung-ho most of the time, ready to down size and leave behind a life of competition and consumerism, occasionally I have moments of apprehension and anxiety. My main concerns are that we will go broke or that I will not enjoy sailing. One of these issues is easy to get to the bottom of; the other might take a bit more creativity!

As Jeff has spent most of his life sailing, I initially thought it would be a good idea for me to learn to sail on my own. I thought that an independent learning experience would give me the confidence and gratification that I would need to feel self-sufficient on a boat. I looked into sailing schools in Chicago and Florida but their courses were far too pricey for what seemed to be very limited experience at the tiller.

Jeff and I had discussed sailing classes before but it wasn’t until we were driving through rural Michigan a week and a half ago that we delved more deeply into why I wanted to take a class. Jeff had just finished reading aloud a story from Beth Leonard’s book Following Seas about a particularly stormy passage her and her partner experienced on the way to Bermuda. As Jeff read the words describing her fear, anxiety, and physical discomfort, I could feel my heart racing and stomach knotting. While I am excited about seeing new places, meeting friendly cruisers, and eating deliciously exotic meals, I am not as enthused about bodily dangers and seasickness.

My rational self believes that some of these fears and concerns can be remedied with more time on boats and a basic understanding of how to sail. And this is where our discussion on me learning to sail began. My knee jerk reaction to the Beth Leonard story put me on the defensive about cruising and made me question my ability to give up the comforts and safety of land life in exchange for the adventure and unknowable challenges of the cruising life. Jeff pointed out that if I wanted more time on the water and, in turn, more time to control the boat and learn how to sail, then our money would be better spent buying a small dingy that we could take sailing in Illinois.

And this is where the used Walker Bay dingy comes into play. Listed at $800 this was at least half as cheap as a week-long sailing class and it would be ours to sail anytime we wanted. So the evening we got home from Michigan, I looked up the Craigslist posting we had seen over the summer and texted the buyers to see if it had sold. Much to our surprise it had not, and we set up a time to view it a few days later.