Column – A retired sailor reflects: Have a thick skin at the starting line

Published 4:02 pm Tuesday, July 11, 2023

I am confident that sailboat racing began when the first two boats or rafts ever equipped with sails happened upon each other, and sailors have been racing ever since — for commerce, for war, as a sport and, almost always, for bragging rights.

After retiring from years of not-terribly-successful racing, a few observations stick in my mind. Among them:

  • Always offer the crew a stiff drink after each race. It’s a time-honored tradition, but more important, it’s a nice way to apologize for yelling at them during the race. Note: The boat should be moored before the drinks are poured.
  • If a crew member accidentally drops a winch handle overboard, be glad you bought the cheap one that floats. If you bought the expensive one that doesn’t, oh, well. You knew it wasn’t a cheap sport when you started.
  • If you care about trivia, you may know that the word boom is derived from the Dutch word for “pole.” Most people who sail more accurately associate the word with its effect on a crewmember who fails to duck during what’s known as a gybe. Boom!
  • Flying a spinnaker (for non-sailors, it’s that really big sail out front on some sailboats) takes practice — a lot of practice. The first time you try launching a spinnaker, don’t do it in an 18-knot wind. We did, and a crew member will forever call it “the day we almost died.” We learned that day that a spinnaker halyard wrapped around the spreader is not a good thing, but it’s very exciting.
  • Always pay extra to buy the automatic inflatable life jacket. The manual one is useless when the spinnaker pole hits you in the head.

Once you’ve gotten the knack of using a spinnaker, you will undoubtedly become over-confident at some point. Not to worry. The spinnaker will quickly remind you to be humble and cautious.

  • The starting line of a sailboat race is one of the most interesting places you can take your boat. You can hear more profanity and see more fists shaken by neighboring boaters than anywhere else you’ll ever sail.
  • Right-of-way is always important on the water and absolutely critical in a race. On opposite tacks, the “starboard” boat has it and “port” boats have to stand clear. Nobody wants to do that, though, and calculating whether you can inch past a right-of-boat without colliding if nobody yields creates some very personal moments between skippers.
  • If a storm’s approaching, secure anything that might be lying around topside. Binoculars bounce, but they don’t float.
  • And a tip to those who sit on the windward rail (the high side) during a race. Tie your shoes snugly. If one slips off, there’s no turning back for it. Ditto, ball caps. Looking aloft during a stiff blow has peeled more than one cap off a head and over the stern.
  • When sailing in little to no wind and against a strong ebb tide, it’s possible — and sometimes legal — to win by anchoring.

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As to sailing generally, a few final thoughts:

If your favorite sailing memories are of sails reefed, water washing over the toe rail, spray coming all the way to the cockpit and all the crew except the helmsman putting their combined weight to windward, then you’re a true Chesapeake Bay sailor. 

If, on the other hand, your favorite memories are those times when you drifted leisurely downwind in light air, you probably should have considered another sport all along.

There are two kinds of sailors on the waters of the Chesapeake and its rivers: Those who have run aground and those who lie about it and say they never have.

And this most important rule: Never pee to windward. It doesn’t take long to learn this. One lesson is usually sufficient.

John Jr. and I spent many delightful days racing together (along with wonderful crew members Jim Groves and Cathy Cooper) and John contributed several of the racing tips above. He also cruised with the family and used the boat quite often as a young man, and from those times he added the following observations.

  • It’s never smart to take your girlfriend sailing with you if you are intentionally trying to knock down a 30-foot sailboat in high winds just to see what it will take to do it.
  • If you are sleeping on the boat and it stops rocking, it’s a very good sign that you’re stuck in the mud.
  • If the breeze is good and your father is at the helm when you decide to go for a swim off the bow, you better catch the line that’s trailing off the stern.
  • And finally, an evening sail and picnic aboard the boat can lead to a long and happy marriage.


John Edwards is publisher emeritus of The Smithfield Times. His email address is