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30 Years of Sailing Reveals 10 Truths of Cruising

30 Years of Sailing Reveals 10 Truths of Cruising
By Stephen Lee
Posted: 2023-02-16T14:00:00Z

In 30 years of sailing, I have developed some catch phrases that sum up a lot of experience.


I call these truths or axioms and use them whenever I sail. These are words a good seaman uses to live by. You probably have your own, or they are variations on these.


Lee’s axiom: A loose line will get caught or tangled. We all know how true this is. You put a line down, pick it up, and it got caught in the dodger frame. You carefully coil the jib halyard and pay close attention as you hang it up. But when it is time to drop the sail, the line is tangled beyond belief. You feel you want to use the method Alexander used to untie the Gordian knot; i.e., take out your knife and cut it.


Cruising is working on your boat in a different harbor. It is supposed to be a nice vacation sail to Block Island. But on the way over, your wife tells you the head is acting up. You end up calling West Marine and having them ship you a part to the island and spend a day repairing the toilet while the family goes biking. Yep, you are cruising. Your house at home doesn’t have an earthquake every day. But in essence, your sailboat does. It gets shaken and stirred. Things break. Being able to do your own repairs is a sign of good seamanship. Don’t complain. Don’t bitch. Just go ahead and deal with it.


A clean engine is a happy engine. Keep the engine compartment clean. Things break including the engine. It is easier to find the problem if the engine area is clean and has clean absorbent pads in the pan. Then leaks can easily be spotted. Also the mechanics like it that way. A happy mechanic is on your side. Does it take extra work on your part? Advanced preparation is the sign of a good seaman. Is this more work? Yep. As above, deal with it.


When in a harbor, go where boats have similar draft. When entering a new harbor I always look for boats like mine. If on a sailboat, don’t go where there are only outboards unless you know the waters. Even in my own harbor I always obey this rule. There are two places in my home harbor where there are known rocks just below the surface. Of course, I never remember where they are. Similar to this: In an unfamiliar harbor, don’t go where there are no boats. There is probably a good reason for their absence.


Pass lobster marks on the handle side: I sail in Maine a lot. That is evident by the next couple. The rope comes down from the other end from the handle and you don’t want to get tangled. Most lobstermen use just a pot mark to mark their traps. Some use pot marks and toggles. Using this axiom presupposes that the lobsterman hasn’t put his mark downstream of the toggle.


You need to know where you aren’t. Like on the rocks. You don’t always have to know exactly where you are. I sailed before the advent of GPS and chart-plotters. I haven’t always known where I was. I didn’t run lines of positions or take triangular bearings. But I have always known where I wasn’t. I may be in the bay but it didn’t matter if I was a mile or a mile and a half from shore. Accuracy is relative to the situation.


Keep a paper chart on deck: Chart-plotters are great. They can give you a good “situational awareness.” But they don’t always give you the big picture. I always have a chart (or chart book) on deck, in plastic. It allows me to see easily what the whole course for the day is going to be. The chart book on deck is the version before the current issue. The current issue stays on the nav station below -- just in case s#*^ happens. 


If in doubt about what lies ahead, slow down. The confusion may resolve itself. If it doesn’t, you are probably in the wrong place. You aren’t where you think you are. Turn around, find a navigation buoy or other known mark and try again. It may take more time, but then you don’t end up with a repair and have to live with Axiom No. 2.


Plan 10 days of a two-week vacation. Things happen. Something breaks. You are deeply in love with this new harbor you have found and don’t want to leave. The weather is crappy. The weather is foggy. The weather is rainy. It won’t be foggy or rainy for two weeks. Just wait and when the weather is good, then continue your trip. If you plan for a different harbor every day, you loose the luxury of enjoying the local scenery.




Don’t go because you “have to make a schedule”. Go because you are rested and healthy and the weather looks good. How many disaster stories have we read where the boat left a harbor “to make a schedule”?


You probably have your own axioms, ones you have developed for your own cruising style. Please comment below. This will be a fun list to create.









Stephen has been sailing the Northeast coast from Digby, Nova Scotia, to Block Island for more than three decades. Like many, he learned to sail at Community Boating in Boston. He currently owns a Freedom 35 and holds a USCG 50-ton Master License. Stephen is treasurer of the Blue Water Sailing Club. 


A version of this article was published in Points East in April, 2013.

Tagged as Cruisingsailing