Sailing School of Hard Knocks

Cindy Wallach and her husband at the beginning of their cruising journey.

I learned how to sail as a kid. Kind of. I managed to point my little Sunfish downwind on Lake Michigan, and then when my parents would yell from shore that I had gone too far, I would jump off the boat, tie the painter to my waist, and swim it back upwind. I was young, and strong, and didn’t have a clue about tacking. But I wanted to be out there; I loved how it felt to have my toes dangling off the side of the boat, sheet in one hand and tiller in the other, wind at my back and sun on my face. I sailed that way, clueless and blissful, for years.

When I graduated from college on the East Coast, Annapolis was just a short drive away. I still had the sailing bug, but I didn’t know anyone with a boat. I was told to head over to the yacht club on a Wednesday with beer and brownies so I could get on a boat for race night. It worked. I lucked into a nice captain and crew on a J/40. They were willing to teach, and I was willing to be rail meat, deck scrubber, and chief chocolate provider. After a few dozen times around the buoys, I figured out the secret of tacking, along with many other things such as sail trim, spinnaker 101, coastal navigation, how to properly coil lines, how to handle an overriding sheet on a winch, and the best way to fold a sail. 

Going round the buoys each week will help you get used to the repetitive grind of sail changes and trim, no doubt, but racing also helped a 20-something me learn a whole lot about human nature. I learned that you don’t question a grown man who believes talking too loud will make that thin breath of wind disappear on a hot August day. I learned that urinating in a rum bottle to save holding tank weight and thus boat speed is not something any girl should be asked to do, ever. I learned that some of life’s best conversations are often had riding the high side of a boat on a point-to-point race. I learned that having fun and maintaining relationships is way more important than winning or a half knot of boat speed. 

A few racing seasons went by, and I met the guy whom I would marry. We decided racing someone else’s boat was taking up too much time, so we decided to buy our own boat together. We said adios to racing and started a whole new world as liveaboards and cruisers. 

Their first passage in the Atlantic Ocean was the "school of hard knocks."

We flew to Ft. Lauderdale in late November and signed our names a lot of times on a lot of papers and became owners of a 36-foot cruising catamaran. We had never sailed a multihull before. We had never sailed offshore before. We had never sailed our home before. Armed with the confidence of youth, a good dose of dumb luck, and lots of Dramamine, we pointed our bow out of Port Everglades into the Atlantic Ocean. 

That passage was definitely the “school of hard knocks Gulf Stream ocean sailing” class. We headed north that blustery November. The Dramamine wasn’t working; the head wasn’t working. Only one engine was working. A new kind of “learning to sail” happened out there. Sure, we understood how to keep the boat trimmed and moving along, but now we learned how to fix an ancient marine sewage line while bucking a late fall Gulf Stream current against the wind. And we learned that the motion sickness meds my doctor-brother gave us created some very real hallucinations. And we learned that cooking offshore is not for the faint of heart or weak of stomach. 

We also learned that stars at sea are the most amazing thing ever. We learned that watching the sunrise on your watch makes everything better. And we learned that a good sense of humor is just as vital out there as a good set of sails. Most importantly, we learned that no matter how much work these damn boats are, we still love this life. One of the reasons I love it is because we never stop learning. There is no right age, or right boat, or right seminar, or right amount of money; you just have to want it.

By Cindy Wallach