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Scariest Sailing Moments


Among all of the scariest sailboat moments, this is usually the first. It may sound silly, but you and your crew risk falling as you board the boat. In all the excitement, people typically make a leap of faith while holding something in one hand or both. The landing pushes the boat just enough to throw it off an inch or down two inches. Boom!
  • Falling down on the boat is infrequent but potentially dangerous. It begins if people feel faint. That’s why Let’s Go Sail ensures that the crew is constantly hydrated. Or people trip. That’s why the lines for the sails are kept tidy and off the deck. The biggest risk is falling down the steps into the cabin. Kids do it all the time, but they can recover quicker than their parents. Hold on as you step down.
  • Falling overboard is rare but recoverable. See Man Overboard below.
  • Falling is much more predominant on a motorboat. In the 35-second video above, a cocky skipper is driving too fast and loses control.


This requires standing up on the top of the boat at the mast to start hauling the main up two-thirds of the way, then finishing by turning on a winch. It’s tricky because you don’t have much to hang onto and can slip. Keep one arm draped around the mast for stability.
Modern sailboats have in-mast features that allow you to turn the winch from the cockpit and simply unwind the main like a window shade. It’s the greatest thing invented for sailing since rum.
Either way, sometimes the sail gets stuck and needs to be shaken loose. This can be stressful because you’re heading directly into the wind, which can make things noisy and flappy. Freeing the slugs on a hoisting main is easily learned. I once had a woman take my three-day WALT course, but all she wanted to learn was how to unravel a mainsail stuck in the in-mast furling. Then she left.

Sailing's Scariest MomentsREEFING

If the wind is blowing over 10 mph, you’ll want to reduce the size of the mainsail by tying off the leech and the luff at the grommets that are visible 3 or 4 feet up from the boom. It’s best to reef in the slip before you go out. Otherwise it’s difficult to do in waters made choppy by the winds. Sometimes while sailing on a pleasant day the winds pick up and you’re forced to reef on the water. Rule: The sooner the better.


The preferred method to turn the boat is to tack into the wind, allowing the boom to gently swing across the boat. Sometimes you need to go the other way, which is called gybing. It’s perfectly okay as long as you control the gybe by trimming the main and hand-carrying the rig over with lines as they meet the traveler.
If you get into the lee of the wind, it will be directly behind you. That can force an accidental gybe that whips the boom across violently. Look for an accidental gybe in Hollywood movies about sailing as a dramatic way to knock the villain into the drink.


Scariest Sailing MomentsA direct hit during a thunderstorm will likely strike atop the mast and zip downward into the cabin, blowing out the electronics. That could cause a fire, which is why you need extinguishers atop deck and below. Here is a rare photo.
It’s highly unlikely that lightening would blow a hole in the bottom of the cabin at the base of the mast. Still, that vision is sufficient reason to have a plan ready to abandon ship. Learn how to send a mayday alert on marine radio to the Coast Guard.


Execution is straightforward. Slowly coast the boat to a complete stop and drop anchor. Then back down in reverse to set the anchor into the bottom. Several things can go wrong.
  1. The anchor doesn’t grab tightly, so the boat coasts around.
  2. The rode and line are too short, so the anchor breaks loose.
  3. The swing of the rode is too small, banging the boat into another boat or a dock or aground.
A corollary challenge is grabbing a mooring ball. Usually a pennant lies on the surface of the water to pick up with a boathook. Do not try to grab the pennant with your hand because you could get your arm yanked badly. Practice mooring with an experienced cruiser.
To avoid anchoring or mooring altogether, go to a marina and spend the night in a transient slip. It’s easier and safer, and it comes with shore cord electricity for air conditioning. Nearby restaurants too.

Scariest Sailing MomentsFOULING

Murphy was a mariner. If a line is free to roam, it will often wind up in the water where it will foul the prop. Keep track of all lines, and tie stopper knots at the ends so they can’t fall entirely in the water.
The prop is also susceptible to fouling from barnacles. In southern climates during the summer, barnacles pile up within weeks. It takes only a half-dozen or so to slow the prop and throw it out of kilter. The engine produces black smoke in an effort to keep up. Wives complain.Scariest Sailing Moments


Unquestionably this is a heart-stopper for the crew. A competent skipper will have enough maintenance training to troubleshoot the problem and have the proper tools handy. If the wind is right, you can always sail back to the marina.
Otherwise, call for a tow boat. Boat US and make thousands of tows every weekend all over America. They are licensed by the USCG specifically for towing. They’ll take you to your home marina and side-saddle the boat back into your slip in a magical feat of boating dexterity. However, the cost can run $900 or more. Find out which service is nearest your marina and buy towing insurance for only $150. Best investment in safety you’ll ever make.


Getting off a boat at the end of the day can be chaotic. Everyone is tired, but they feel experienced enough from the sail to be confident about disembarking. The key is to make sure everyone has their hands free to grab shrouds and piers to hold onto as they step off. This is when people trip or slip, falling into the water or onto the dock. The only solution is vigilance by the skipper, who for etiquette and practical reasons should take everyone’s hands or arms to guide them off.

Scariest Sailing MomentsMAN OVERBOARD

A shocking event, to be sure. Someone standing on the bow of the boat suddenly falls over. Skipper and crew need to learn the Figure 8 method of MOB rescue as it’s proven and quick. If a child goes overboard, turn quickly to grab Mom because she’ll instinctively try to jump in. Trust me, one victim in the water is plenty.


Returning to a slip is the single biggest worry among boaters—and their spouses. All you have to do is slow down to the smallest speed possible while still propelling the boat. Say 1-2 mph. If you stop prematurely the boat will stall out and begin to drift. Start by entering bow-in because it’s easier to handle and stop. Eventually you can learn to back into a slip, which is very cool. In the video below, jump to 3:20 mark to see a proper slip docking. Set up a 90 degree angle to head in directly, then ease off the power as you draw near. Flip into reverse to stop the boat quickly.

Running Aground

Two couples from New Jersey and one couple from Pennsylvania spontaneously sailed on a hot day when the wind picked up. Rob Frank observed that the York River is as big as the Raritan River back home, where he has boated frequently.
Scariest Moments Sailing“My cousin Jesse and I ran a 23-foot skiffe right up onto the beach one night. We had no idea it was there. It was dark and we were drinking. Fortunately it was at low tide, but we had to spend the night there. We got it off the next morning. Fortunately it wasn’t my boat, but Jesse’s.”
Just then, a motorboat past fast off our bow, not too close but noticeable nonetheless. Rob said, “I’ve had my troubles with sailboats, so I tend to avoid them in a motorboat.” I suggested, “Maybe that was Jesse.” He laughed.
Scariest Moments SailingHarry Keller ran the helm for hours as we tacked downriver five or six times before taking three long tacks downwind. The wind was picking up nicely and creating 2-foot waves on the aft quarter. “I was on an aircraft carrier in the Navy when we got hit by a big storm. The bow was taking waves completely over the flight deck, continuously. The storm lasted for days, so we sailed out of it to get away. The ship was beaten up so badly that we had to go into dry dock to fix the runway. It had peeled off the bow and curled up.”
Scariest Sailing Moments
Sailing on the Fourth
Scariest Sailing Moments
Quite appropriate for the Fourth of July, newly minted Army officers from Ft. Lee went sailing in steady winds from the east. We were sailing past the Yorktown Coast Guard Training Center in time for the 12-gun salute by cannon at precisely noon. Jennifer French and Clayton Walker are second lieutenants who just finished the Basic Officer Course. They brought their pal Chris Frank, who took the course as a civilian for the Department of the Army.
Jennifer explained, “The Army has combined Ordnance, Transportation and Quartermaster into one extended 16-week course as an experiment to cross train us in all three functions of logistics.” In my day at Ft. Lee, the course was strictly Quartermaster and ran eight weeks.
Scariest Sailing MomentsI asked if they stayed in the BOQ. “What’s that?” Jennifer said. “We stay in a hotel, an IHG Holiday Inn.” Clayton said, “It’s the largest Holiday Inn in the world, with four miles of hallways.”
Clayton grew up in upstate New York and boated on the St. Lawrence River. He was impressed with the York River, to a point. “The St. Lawrence is crystal clear, and very deep. Of course, we get some big storms off the ocean. Afterward, one time we found three deck chairs and a cooler floating in the water. One of them was an Adirondack chair that had blown from an island three miles away.”Scariest Sailing Moments
Jennifer handled the helm with aplomb, and all three took a turn. She grew up in Iowa as an Army brat daughter of an Army recruiter. “Iowa is what you’ve heard. Everyone is white except for that one black student in class who everyone befriends because it’s cool. Friday night is for football. There are no Lexus cars, just Fords. The corn grows high in the field.”
She went through OCS after a stint as a TV reporter. “She has her own You Tube page as an investigative reporter,” Clayton said. “Look it up.” For a brief moment, we saw dolphins in the distance and then they disappeared. Scariest Sailing Moments
After six tacks downwind, we turned and put up the spinnaker. The team caught on quickly as we gently sailed upriver. Jen is deploying to Kuwait and talked about her parents. “I’m trying to reforge a relationship with them as adults, so I have taken them out to dinner. Took them to an Eighties place where they danced disco together. It was sweet.”
Chris said, “I took my parents to a bar at Virginia Tech, and the bartender knew me by name.” My mom asked me, “Do you come here often?”

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Scariest Sailing Moments
Article Name
Scariest Sailing Moments
The scariest sailing moments include lightning, sinking, man-overboard, anchoring, docking and fouling. You can beat them all, with a little training.
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Williamsburg Charter Sails
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