If you’re new to cruising, there are things you have to know immediately—and things you don’t. Huh? For example: Initially, you can ignore the finer points of sail trim (if you don’t mind drifting across oceans at a snail’s pace) but you must know how to reef your sails (so you don’t lose your mast) and how not to jibe (so you don’t lose your head).
Yes, it’s crazy but greenhorns who aren’t sure where the end of their boom goes within a yard or two are constantly asking me if they should buy Dyneema for their mainsheet to eliminate that quarter of an inch of stretch during gale-force gusts.
“Only if you have more money than Elon Musk and Bill Gates put together,” I smile.
One thing a sailor should remember if they want to impress their crew is: never act surprised.
Recently I carried my light-air genoa into an Indian Ocean squall and said to my wife in the galley below as the sail shredded, “…no need to come on deck, honey—I took a ribbon reef in the headsail!”
Ditto, when you go bouncing up on a sandbar, “Oh, goody—we don’t have to get the chain muddy!”

If you wrap a sheet in the prop, just quip, “…that’ll stop the damn thing from spinning!”
No, I’ve never dropped my chute in the water—but, yes, I have trolled for shrimp in the middle of an ocean race.
*Casting off while leaving the power cord plugged into the dock is a common occurrence. I just nonchalantly laugh as I cast off the sparks, “Oh, well! We should exercise the gen/set anyway!”
Here’s another hint: Why not conscientiously check the structural integrity of an unfamiliar dock while tying up—isn’t that just common sense? Yacht stems should be built strong, right? I mean, what red-blooded sailor wants a stem weaker than his morals?
Under the heading of ‘best laid plans’: I’ll never forget going to sea for the first time with my new forward-scanning depth meter—and backing into that frothing reef. Damn!
Actually, I’m kinda amazed how cheap my annual yacht insurance premium is—if I’m not aboard.
Growing old aboard with grace and wisdom is difficult. I’ve taken to guiltily pouring my laxative into 151 rum bottles during raft-ups.
Here is another pro-sailing tip: never needlessly accept the blame. Once a student of my celestial navigation course set off for Cozumel from New Orleans—and ended up attempting to speak Spanish to some shell collectors on Clearwater Beach.
Oophs!
Nonetheless, when I heard the news, I remarked with a poker face, “…must have forgotten to wind his chronometer!”
Back in the days of sextants and chip logs, I once missed Bermuda by almost a week. I explained it away to my gullible wife by muttering, “…damned continental drift!”
The Pacific Ocean is big enough that nav mistakes are common. If the guy catching my dock lines is munching a croissant, I figure Tahiti. If he’s baaaashfully hugging a reluctant sheep, I figure New Zealand. But if he wants to beat me up over such crude cultural generalizations—definitely an Aussie on a Friday night!
Be particularly careful in Fiji if young people ask your religion. Their ancestors have told them that Christian missionaries—with their extra layer of fat—were particularly tasty. Accept invitations to dinner; never for dinner! Avoid any community meal in which ‘long pig’ is served—that would be you, dude!

Yes, sailing lingo is important.
The truth is, I brook no resistance while helming. If my wife is getting too feisty, I just say, “Shall we practice a COB—a chick-over-board drill?”
That shuts her up.
Another thing to remember is not to be too subservient. Sure, it is nice to learn the ropes while club racing, but if you’re helming for the first time and the owner tells you to “fall off,” don’t step over the lifelines until he repeats the request at least twice.
Ditto, if a female owner gives you the opposite command. (Hopefully, the archaic ‘harden up,’ will be dropped from our sexist racing lexicon soon—along with all the other suspect spinnaker-related pole-tip commands as well.)
A Hysterical … er, I mean, Historical Perspective on USVI & BVI Marine Industries
Women on the race course can be a problem. My wife always says, when asked what our racing handicap is, “My husband Fatty.”
It’s true. I’ve been passed by jellyfish. In the tropics, sandbars silt in faster; in the polar regions, glaciers have out-paced me to windward.
I don’t have a stopwatch to time my racing starts—a Week-at-a-Glance calendar does just fine. Yes, we carry binoculars—how else would we know the boat’s name on the transom of our nearest competitor?
The way I figure it, if I can see other vessels behind me as I finish a race—I didn’t come in DFL. (How would I know which vessels are participating—it isn’t against the racing rules to anchor or pick up a mooring, is it?)
All of this, my wife is quick to point out at the yacht club. “Our anchors affect our speed only slightly,” she proclaims. “Our biggest problem on the racecourse is other boats swing alongside to ask if we’re aground.”
Oh, she’s ego-bruising all right. “Once during the Caribbean 1500 we put out our Paratech sea anchor when hit by a gale in the Stream—and forget to bring it back in. On the plus side, we placed quite well in the following year’s event…”
Merely because someone has sailed a lot doesn’t mean they’re infallible. Just because you’re trying to dislodge the other fellow’s spare bow anchor from your stern rail doesn’t mean he didn’t drag… upwind… in a gale.
Here’s another pro-tip if you race around Jamaica—head up has nothing to do with marijuana.
It’s best not to buy a wooden craft as your first vessel. Some rotten ones have more holes than a spaghetti colander. My first carvel-planked craft had more leaks than the White House. The only thing keeping her together was the roaches holding hands.
Her garboard plank was softer than Bob Dole.
She had more (teredo) worms than a bait shack!
…no, these aren’t the type of ‘woodies’ modern bilge bunnies demand.
Yes, there’s sooooo much misinformation out there!
Caribbean storms can be stressful—don’t believe for one second that hurricanes are ‘low pressure’ events.
Once in Madagascar, I raced where primitive participants were allowed to beat each other bloody with heavy wooden oars at the finish line—that brought a whole new level to my understanding of ‘club’ racing.
Modern marine diesels are another topic where confusion exists.
If your engine won’t even turn over—check your lead-acid starting batteries to confirm they’re ‘full of juice.’ If not, there’s your problem!
If you run a diesel out of fuel, you’ll have to bleed your system. Traditionally, this starts with the owner’s wallet and quickly moves onto his bank account—then drains all the other resources aboard as well.
Prop drag is a problem. I now have a Max prop—after years of experimenting with normal three-bladers that I hacksawed and hinged. My advice is to ignore feathering props. If you do get involved in experimentation, use feathers from seabirds as they don’t absorb water.
No, that isn’t an engine-hour-meter on your instrument panel—that’s how much you will have to spend on Caribbean marine mechanics (in hundred-dollar increments).
Back in the day, sails were called ‘rags’ because that’s what a sailor dressed in after paying his sailmaker.
Yacht racing is one of the few ‘self-enforcing’ sports for gentlemen. This means that you should never cheat if another competitor might notice. Ditto, the race committee: Yes, you can hit the leeward pin of the start line on the side away from party-boat-with-all-the-cocktail flags—but never on the side in view of it.
…that’s just Racing Rules 101 stuff.
If two boats on opposite tacks approach, be the first to yell “…starboard!” You have a 50% chance of being right. And even if you’re not, your competition will have to mentally hesitate… Well, if they have any integrity, they will.
While it is best to avoid serious collisions during, say, the Rolex regatta, it is also true that the crews of sunken vessels often miss the protest hearing. (It’s this type of ‘insider’ advice you never read online in Scuttlebutt!)
What else do you need to know about international regattas other than that, traditionally, all marriage vows are suspended? Remember to always bring protection—from rain and in the pocket of your foulies, from the local ladies. Well, yes, there are regional differences. In the Caribbean, rum is the answer but most participants are too high on ganja to remember the question.
Sexism is, alas, beginning to be frowned up. No more ‘bilge bunny’ talk, please. Ditto, rail-rider, sailbag, and dock box. If the owner’s arm-candy asks mid-race why everyone is scurrying around the deck changing sails on the downwind run, just tell her the truth, “…we’re bored with the colors!”
Yes, local knowledge is important—but never ask a proud Antiguan Rasta about ‘package’ size. He’ll always smile widely and say with confidence, “…not by the size of de hand nor de feet—but judge by de length of de dreds, me son!”
This brings us to the subject of yacht maintenance. People think I don’t do any. Not true! Even my long-suffering wife Carolyn will back me up. “He consistently maintains his sense of humor and, additionally, energetically polishes the head seat twice a day!”
During our last haul-out in New Zealand, I watched my wife sanding our hull intently—well, up until I got eyestrain and had to rest. (Truthfully? I was horrified by her lack of compassion!)
(Bio note: Fatty and Carolyn continue to be awash in a sea of financial ruin.)