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It's What You Don't Know You Don't Know


"They sold everything and bought a boat to sail the world. It sank on day two."


I saw this story the other day and it reminded me of why we take what we do so seriously.

Apparently, this couple were attempting to make a run through an unfamiliar inlet, at night, in conditions of severely reduced visibility, and in a vessel whose true condition and seaworthiness evidently remained a mystery to her owners.
sunken sailboat
Credit: Jim Damaske | Tampa Bay Times

Seems they hit an underwater obstruction, a rock perhaps, shearing off the keel, causing a capsize in which the boat was left without the ability to right itself. 
Sure, it's easy to sit here and second-guess these two for their ambitious plans and woeful lack of experience — along with what seems to be their complete ignorance of the fundamentals of good seamanship.
It's easy to criticize them for quitting their jobs and following their dreams without a financial safety net.

And it's a easy to say, "that's what you get for putting to sea on a 50-year-old boat!"
But the truth is, anything can (and often does) go wrong ...despite all the experience in the world and even with the most seaworthy of vessels. And overconfidence & arrogance can be just as deadly as the double-whammy of complete ignorance combined with inexperience. 

History is full of such examples.

The RMS Titanic charged out into the North Atlantic from Southhampton, England, on April 10, 1912, solid as a rock. Her captain and crew well-seasoned. That fateful night of April 14, 1912, the night sky was crystal clear and the ocean as 'calm as a millpond.' But the ship was being warned of ice in the area. 

The prudent thing to do in their case was to slow down

But of course, Titanic was built for speed, and her skipper, ignoring all of his extensive experience, and the danger, felt confident that he and his ship were somehow different. Somehow immune to unexpected, bad fortune. 

The rest is history...and laying at the bottom of the ocean.

Piloting Skills Are Critical

In the case of this young couple and their capsizing, perhaps the most egregious sin they may have been guilty of (and I'm just guessing, because it's all too common nowadays) is relying solely on one source for position determination. 

Like a GPS chartplotter. 

The boat's skipper claimed they struck something that wasn't on the chart, which certainly is possible. 

But more often than not, the relevant object is on the chart and the boat is somewhere other than where the skipper believes it to be. 

In his authoritative text, Piloting and Seamanship, seamanship expert Charles Chapman writes:

"It is your duty as skipper to make careful judgment as to the precision and frequency with which your vessel's position should be fixed, and then to see that these fixes are carefully obtained and recorded."

The necessity for this hasn't changed...even in the age of generally highly-accurate GPS equipment like electronic chart plotters. 

Chapman goes on to say: 

"Your ability to determine your position with appropriate accuracy under any conditions of visibility at sea is critical. Your limitations in these skills must restrict the extent of your boating activities, setting the boundaries of the waters and weather conditions that you can accept without endangering your boat or its crew." 

When I was in my 20's, I had the same dream of abandoning a "normal" life ashore just like these two intrepid souls, of buying a cheap (decades old) sailboat, living aboard, saving what money I could and eventually setting off on my own and learning it all as I went. 

A healthy dose of self-doubt and fear, however, kept me from making the leap. Fear borne not of the thought of single-handing a boat alone on the ocean, but of what I didn't know that I didn't know. 
No one, and I mean, no one, can ever possibly know it all. No matter how prepared, cautious, experienced and informed you are when going to sea, there's always an element of risk. 

In his outstanding book on the subject, John Rousmaniere writes in The Annapolis Book of Sailing and Seamanship: "Seamanship is an ever-expanding set of skills, and much more. Seamanship is an attitude, a hope, an ethos. It's a quest that guides us...seamanship is a both a technical discipline that you will never stop mastering and a caring, alert state of mind we must never cease developing and improving." 

The author goes on to describe how knowledge and sound seamanship, regardless of the quantities of each one may possess, never fully protect us from the ever-present risks that accompany us whenever we take to the sea: 
After a series of serious sailing accidents in 2011 and 2012, a sailor asked this question in Scuttlebutt, a sailor's blog: "How does the average sailor get enough experience to be safe at sea? 

In reply, my friend Brad Avery, who is director of the Orange Coast College Sailing and Seamanship Program in Newport Beach, California, said that the premise that there can be "enough" seamanship is mistaken. 

"We are never safe at sea, whether we are professionals or amateurs. We are always one bad decision away from disaster. My goal is to sail error-free on each cruise or race, but I know this is impossible to achieve. The quest for a voyage free of mistakes goes on. Time on the water, training, humility, and constant vigilance are the keys to being 'safer.'"

Avery concluded with these words: "Knowing you're never safe also helps." 

Thoughts like this run throughout maritime history. (Joseph) Conrad expressed the idea a little differently: "A seaman laboring under an undue sense of security becomes at once worth hardly half his salt." 

Herman Melville wrote in Moby-Dick that the good mariner "feels just enough of trepidation to sharpen all his faculties." 

Complacency is foreign to seamanship. 

Every time an effort has met with success, we should humbly decline to claim too much credit. Circumstance, luck, and other factors far beyond our control inevitably play a part.

Absence of failure is not, in itself, a proof of absolute success. The best sailors I know are deeply concerned about seamanship and safety. 

To quote an able seaman with whom I have sailed many miles, Howard Lapsley, "Safety and performance are not mutually exclusive." 

 If you've been bitten by the sailing bug and are itching to leave shore-life behind for a grand sailing adventure of your own, come sailing with me and Skipper Bud. 

Learn a little bit about "what you don't know you don't know." 

Gain as much real-life experience as you can possibly get...and remember that "local knowledge" is priceless. 

No one really disputes that there is simply no substitute for experience and time on the water, acquiring it in all conditions, day and night, on different types and sizes of vessels. 

One day at a time.

Suggested Reading

If you're interested in building your sailing experience upon a solid foundation of "book knowledge," and learning from the wisdom of experts who've gone well ahead of you, here is a list of must-reads that I highly recommend to anyone — regardless of experience level: 
The Annapolis Book of Sailing and Seamanship4th Edition. John Rousmaniere. 2014

Piloting and Seamanship
, 67th Edition. Charles F. Chapman. 2013

Sailing Skills and Seamanship, 6th Edition. United States Coast Guard Auxiliary. Edited and revised by Paul DeVita. 2008

Fast Track To Cruising. Steve and Doris Colgate. 2005.

How To Read A Nautical Chart
. Nigel Calder. 2003.

The Complete Sailing Manual. 4th Edition. Steve Sleight. 2012. 

Seaworthy: Essential Lessons from BoatU.S.'s 20-Year Case File of Things Gone Wrong. Robert A. Adriance Jr. 2006. 

Sailing Around The World Alone. Captain Joshua Slocum. 1899. 

Bowditch's American Practical Navigator. Nathaniel Bowditch. 1900. 

United States Coast Pilot 5. National Ocean Service/National Oceanic and Atmospheric Administration. 2017. 
Navigation Rules & Regulations Handbook. August 2014 Edition. Department of Homeland Security & United States Coast Guard. 2014. 

Local Notice to Mariners. National Ocean Service and Department of Homeland Security & United States Coast Guard. 2018

Light List. Vol. 4. Department of Homeland Security & United States Coast Guard. 2018

Happy reading! 


— Capt. Kris

Many of our guests who come cruising with us bring a nice lunch and drinks with them and enjoy it on the boat. 

This crew pretty much "forgot" lunch and instead just brought the drinks....a case of beer and a bottle of Hornitos® Tequila.

They had a great time. 

And then they got really hungry! 

When you charter a private sailing cruise with us, you'll have the Old Glory all to yourself. What we do on your cruise is completely up to you...and that includes where we stop for lunch. 

On this occasion, we were sailing a southeasterly course, roughly following the 1 fathom depth curve line on our chart, which kept us close to shore as we sailed down Estero Island, past Fort Myers Beach. 

It turns out that right about when this group got hungry, there was a great place to nearby to grab some grub, right on the beach: Pinchers Crab Shack. 


We pulled in close to the beach (as close as we could without risking a grounding), and dropped our hook (the anchor) in about 5-6 feet of water. 

Though the water temp was about 75 degrees (chilly by my standards!! I only start swimming in May!), this group nominated three brave souls (all of them women) to jump in and swim/wade ashore to grab lunch. 

Using their cell phones, it was easy for them to dial up Pinchers and order their lunch on the boat...and then SPLASH! SPLASH! SPLASH! 

Three ladies went over the side (we're saving up to buy an outboard motor-powered dingy for the boat...), and although they couldn't touch bottom where we anchored, it was a very short, easy swim (in calm water, mind you) to the beach...while the guys waited onboard, guzzling beer (I know, I know...typical, right?). 


The ladies killed some time ashore on the beach, while the guys hung out on the boat with me and Skipper Bud. 

But they were back before long, making their way through the water (even swimming with it as they got closer to the boat, in water just over their heads) with lunch for themselves AND an AWESOME cheeseburgers and fries for the Captain and I securely protected in plastic bags, along with their cell phone and credit cards too! 

What a FUN cruise this turned out to be... everyone enjoyed the lunch from our friends at Pincher's, and then it was time to make our way back to the marina. 

After more than 160 cruises I've done with Skipper Bud, this was one for the Hall of Fame! 

Join us for lunch or dinner any time! 

There are lots of places just like Pinchers were we can either anchor offshore nearby, or, pull up to a dock at the restaurant...and you won't even have to get wet!!

— Capt. Kris


The Perfect Family Sunset Cruise on Catamaran Old Glory


No matter how many times I've been out sailing with Skipper Bud on the Old Glory catamaran (160+ cruises and counting!), I always find something unique to cherish.

Sometimes it's a spectacular sunset, or seeing a dolphin jump clear of the water...other times it's the wind, blowing hard enough from just the right direction to give us perfect sailing conditions. 

On this occasion a few weeks ago, it was the very special treat of being joined by my new son, Benson, for his first sunset cruise.

Though he's only 6 months old, and still too young to enjoy it for himself, having him out with us instantly became one of my life's best memories.

Skipper Bud knows how much I love a sunset cruise, and on this day, he happened to have the chance to offer the boat to me and my family for the afternoon. And we jumped at it! 

My wife Liz and her parents, who are visiting from Holland, have all been out with Skipper Bud before. But this was the first chance we had to bring Benson along for his first sail. 


He even took a turn at the helm with daddy! 

Admittedly, it was A LOT for him to take in...but as they say, you gotta start 'em off young!

There was some initial trepidation on my wife's part about taking him offshore and keeping him awake so long. We weren't really sure how he'd do out there. 

The wind that day was out of the northwest at around 10 knots, but since the channel we sail out of (Matanzas Pass) is behind Sanibel Island, the wind and waves closer to shore were almost calm. 

Once we got about 3 nautical miles offshore though, we cleared the lee of the island (the side opposite the wind direction) and got into a really nice breeze. Skipper Bud had our sails trimmed nicely and we were able to sail to within 40 degrees of the apparent wind, on a wonderful close reach. 

Wave height and period were no issue at all — it was a comfortable ride on the catamaran for sure, and truly, the kind of conditions where our boat really shines.

I should point out; if we had been sailing on a traditional sailboat (a "monohull"), the breeze would have had us heeling over sharply. Which can be fun, for some. But we would have been hanging on for balance when going forward or aft, and bracing ourselves to remain seated upright in the cockpit. 

Instead, our catamaran stays upright when the wind picks up. This means you can do things like sit a drink down on the table in the stern lounge without it tipping over and spilling. And you can relax without any effort whatsoever. 

That's certainly how I like my sailing when I'm with my wife and family. 

It took us about an hour and a half to reach the Three Nautical Mile line out in the Gulf and little Benson was doing great but starting to get fussy from a missed nap time. 

This was our coming-about point. 

With me at the helm, Skipper Bud handled the jib sheets like a pro and together we managed to execute a fairly flawless 180 degree tacking maneuver. With the boat now headed on a reciprocal course in the exact opposite direction from whence we had come, we started our journey back to the marina. 

Mother Nature saved the best part of the cruise for last. 

Just as we began making our way back up the channel, the sunset was setting astern over our shoulders and putting on the most magnificent display of light and color. 

At the mouth of the Pass, we encountered about a dozen boats of all descriptions gathered for the show. Everyone had their cameras out, capturing the magic of the moment: 

The sunset, sinking between two daybeacons marking the boundaries of the channel and the Sanibel Island Light rising from Pt. Ybel in the distance made for the perfect picture. 

The perfect ending to a perfect cruise. 

I'll never forget it. And I'll cherish this special memory for the rest of my life. 

Thanks Skipper Bud!!!


— Capt. Kris