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Eight Things Every Daysailor Should Know

As a 30-year veteran daysailor, I feel a moral obligation to spare you some of the physical and emotional pain I’ve faced over the years. I’m talking about daysailing’s dirty little secrets, the bilgewater of our sport. Feel free to take notes.

As a 30-year veteran daysailor, I feel a moral obligation to spare you some of the physical and emotional pain I’ve faced over the years. I’m talking about daysailing’s dirty little secrets, the bilgewater of our sport. Feel free to take notes.

1) Sailing wreaks havoc on your toes.
A sailboat deck is a minefield of fixed metal objects capable of causing excruciating pain. Winches and blocks, cleats and stanchions, tracks and stays—all are waiting to injure your unsuspecting tootsies. Trips through the minefield can’t be avoided, nor can the well-practiced string of obscenities that follow. Wear boat shoes if you care about your feet or the sensibilities of your crew.

2) Don’t ever forget the blue stuff.
Most smaller sailboats have portable chemical toilets with small holding tanks that require periodic emptying. If you’ve prepared the tank properly by adding more than the recommended amount of blue liquid deodorizer, the job is at best repulsive. If not, you’ll sell your boat as soon as you stop gagging and buy one with a fixed head. Never forget the blue stuff!

3) Beware arachnophobes.
In choosing guests for a daysail, it’s important to know if they have any phobias—especially an irrational fear of spiders. These creatures are frequent stowaways and sudden appearances are not unusual. Leave arachnophobes ashore, where they have room to run.

4) Going backwards is embarrassing.
You’ll notice most experienced sailors choose to back into a slip while the less experienced come in bow-first. This is because backing a boat can be challenging, but boarding a boat whose bow is pointed toward the destination can be preferable. Before attempting to go stern-to with your new sailing buddies watching from the dock, do your ego a favor and get some practice.

5) Most powerboaters don’t like you.
It’s not anything you did, but how you’re perceived that’s the problem. As a sailor, you’re seen as a snob—an elitist who likes fine wine and drives a BMW. Fueling the resentment is the rule that gives you right-of-way. So don’t be surprised if a 20-footer with twin 250s cuts off your nose. Just raise that wine glass, pinkie extended (or another digit, if you must), and toast him as you would that offending piece of deck hardware.

6) Special guests guarantee dead calm.
Have special guests to impress? The boss maybe, or some old friends? Better make sure your fuel tank is full, because you won’t be doing much sailing. In fact, if the wind has her way, you’ll be doing more flailing than sailing. And when you go forward to lower the jib, make sure you’re wearing boat shoes. Chances are the boss’s wife won’t appreciate your expletives.

7) Mast envy is inevitable.
“His is bigger than mine.” Men have been grappling with this feeling of inadequacy for centuries (thank God for Michelangelo’s David). Mast height is difficult to ignore, but just because yours is shorter, don’t go out and buy a bigger boat. Many sailors who have moved up in size miss the close connection they had with the sea. Be proud of your short mast.

8) You are the standard bearer. (This is the best kept secret of all.)
Sailing offers many choices. Some choose to race for the thrill of crossing the finish line first. Some choose to cruise for weeks at a time, exploring new anchorages and towns along the way. Still others make their homes aboard, crossing oceans in search of adventure. And then there are the daysailors, who sail simply to sail: to feel the heel of their boat as the sails fill; to listen to the music of the water; to feel the cooling spray off the wave tops. In spite of the annoyances, I can’t think of a better way to spend a day.

Have some tips of your own to share? Email us at sailmail@sailmagazine.com and if we like your list, we'll publish it!

Photo by John Neal/Mahina Expeditions

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