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Learning to Sail in Maine on the Penobscot Bay

Sailing Penobscot Bay — I am learning how to sail in the Penobscot Bay of Maine near Belfast. I have discovered that in order to learn how to sail I need to take my face out of the ‘how to sail’ books and get in a boat on the water. Through meeting a friend and [...]

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Sailing Penobscot Bay —

I am learning how to sail in the Penobscot Bay of Maine near Belfast. I have discovered that in order to learn how to sail I need to take my face out of the ‘how to sail’ books and get in a boat on the water. Through meeting a friend and a much appreciated sailing invitation, this is exactly what I did.

“Self preservation is overrated,” boldly spoke a member of the sailing party just before we unhook the ship from its mooring.

Not one hour later, this same fellow was holding on for his life and screaming in fright.

And such seems to be the world of sailing. For a moment, the water is as smooth as a piece of handblown glass — gentle undulations and ripples of wind push you through the water — and the next the boat is tipped up sideways with the wind blowing hard and waves crashing over the bow.

Sailing is fun.

My sister, Nicky, just stared at the fellow who quickly lost his boldness with a smirk creasing the sides of her face. She could hardly contain her laughter, as she was cool as a cucumber as the boat teetered up on end in a splashing sea as the big, brave man sitting next to her was shaking for dear life.

Throughout this, I was learning how to man the tiller and jibe the little sailboat in a moderate wind off of Turtle Head in Penobscot Bay on the coast of Maine.

Racing Sailboat in Penopscot Bay

Racing Sailboat in Penopscot Bay

My sister and I were out sailing on a newfound friend’s 26 foot racing sloop, and loving every minute of it — waves, wind, and all. The Shepard siblings smiled as the ship’s captain taught us a few of the basics of sailing. I watched as my book honed knowledge of sailing took shape in the wind and water world.

“Ah, so that is how this works,” I found myself thinking each time a point that I came across in reading made the jump from theory to reality.

I watched the sails interplay with the wind, and I tried to guess what move the captain, B., would do next. Sometimes I could figure it out — “we need to tack here, around now would be a good time to jibe” — sometimes I could not — “what the hell was that move!?! Our tail end made the turn for us!?!” –but through it all B. seemed to smile to himself over the greeness of his crew, and offered his instruction on the broader points of sailing.

Sailboat captain in Maine

Sailboat captain in Maine

“What is port and starboard?” he quizzed us.

“Left and right,” I answered simply — I had grown up reading my Conrad.

“What color is for port and what color is for starboard?” our test continued.

Not wanting to bogart all of the questions, I let another member of the crew answer this one. And the screamer answered correctly.

“Port wine is red so that is a way to remember that the port side of a boat is red,” another guy on the sailing party chimed in, and then continued, “green has more letters than red and starboard has more letters than port, so that means that green is for the starboard side.”

Helpful hints, I suppose, though I could not help but to rely on route memorization for this one.

Sailing in Maine's Penopscot Bay

Sailing in Maine's Penopscot Bay

B. then pulled out a rope and asked if anyone new how to tie a bowline.

I remembered the diagrams from the books, though struggled bringing it to life.

B. took the rope and made a loop with it.

“This part is the tree,” he spoke while indicating the part of the rope that went off and connected with the boat that was under the loop. “And this is the rabbit,” he spoke as he hung on to the end of the line. “What you do is you take the rabbit and put it through the loop and then wrap it around the tree and then tie it off through the loop again.”

“This is the most important knot in sailing,” B. continued, “you can see bowlines all over the boat. This knot is good because you can tighten it easily, it won’t loosen, and, no matter what, it won’t jam.”

B. then showed us how the knot could be untighted with only a simple push up on one of the turns, it was sort of like raising a lever. The three men of the crew looked upon B. tightening and untightening the bowline with absolute awe.

The absences of a round of “ooos” and “ahhhs” was the only thing that kept us three greenhorn men from becoming B.’s audience rather than his crew.

My sister looked at us as if we were geeking out — we were — “It’s only a f’cking knot,” I could see her thinking.

I looked around the boat, there were bowlines connected to sails, to rails, to everything. To my tactical manly senses, the bowline was obviously not only a f’cking knot.

I practiced making bowlines. I fumbled it once, I fumbled it twice, I fumbled it a third time. Then I just tossed the rope back down on the deck and pretended that I knew how to do it. But my cool was not as strong as my desire to learn, and I quickly picked up the line again and asked for another round of instruction.

I nailed it. Ok, good, I was no longer cool but I was now able to tie a bowline knot.

How to tie a bowline knot video

The last time that I went out sailing with The Captain on his 28″ cruiser I received a very hands on instruction on tacking. This time, as I sailed with B. with the wind at our backs, I would learn how to jibe. Jibing seems to be very much like tacking, the major difference is that you do it while traveling downwind rather than upwind. But the dynamic is similar: in order to continue traveling in your intended direction, you need to change your boats angle to the wind and flip the sails to the other side.

“A jibe or gybe is a sailing maneuver where a sailing vessel turns its stern through the wind, such that the wind direction changes from one side of the boat to the other.” –http://en.wikipedia.org/wiki/Jibe

How to Jibe a Sailboat

B. then explained that jibing is vastly more dangerous than tacking, as there is no point where the sails luff — are released from wind pressure — throughout the maneuver. So the wind is fully exerted on the sails when they are on one side of the boat, and then it blows them right over to the other side of the boat in very quick order.

B. sheeted in the boom, which is the long bar on the bottom side of the main sail, and we went into a jibe. I was at the tiller. I was told to direct the boat to turn down wind and then to give the tiller a little jolt to get the boom to switch sides. I did this in a 12 knot wind, and the boom flew from one side of the boat to the other and the tilt of the little vessel in the sea quickly followed its sail. The crew then switched sides of the boat and we continued on our way.

If a man happened to be standing up in the cockpit the moment the boom shifted sides, I am afraid to say that he would no longer be the possessor of a head, as the main sail jumped from one side of the boat to the other with a touch of vengeance. But the commotion simmered down as quickly as it rose up, I straightened out the boat, and we sailed smoothly once again.

How to Tack a Sailboat

Learning to sail seems to be much like learning to ride a bicycle exponentiated to the 100th power. But although sailing is vastly more complex than bicycling, the approach is similar: you can read all day long about how to ride a bicycle, but this will not make you any more able to do it; to learn how to ride a bike, you need to find an old two wheeler, strip off the training wheels, and ride it without regard to how many times you fall down. For each mistake you make — each time you do a face skid on the pavement — you will only be brought a little closer to learning how to ride without fault.

To learn how to sail I need to get out on the water and learn the ropes with my hands, learn to gauge the wind with my eyes, and learn to feel the boat and the sea with my entire body. The only way to learn to sail is to sail.

“Sailing,” my wife says, “is just one of those things where you need to be out on the water in a boat to experience in order to learn.”

Learning to sail in Maine on the Penopscot Bay Photos

Wade at the helm learning to sail

Wade at the helm learning to sail

Wade and sister Nicky

Wade and sister Nicky

26 foot racing sailboat in maine

26 foot racing sailboat in maine

Nicky and B. returning to land after sailing

Nicky and B. returning to land after sailing

Vagabond Journey on Wade’s sister Nicky

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Learning to sail series

[seriesposts listtype=ul orderby=date order=ASC name=”preparing to travel by sea” ]


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Filed under: Boat Travel, Maine

About the Author:

I am the founder and editor of Vagabond Journey. I’ve been traveling the world since 1999, through 91 countries. I am the author of the book, Ghost Cities of China and have written for The Guardian, Forbes, Bloomberg, The Diplomat, the South China Morning Post, and other publications. has written 3716 posts on Vagabond Journey. Contact the author.

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VBJ is currently in: New York City

4 comments… add one

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  • baron September 10, 2009, 12:36 pm


    You’re making me want to get back into sailing. I hate you.

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    • Wade | Vagabond Journey.com September 11, 2009, 6:56 pm

      Haha, it is fun, man!

      Sailing seems to be one of those things that if it gets you it will keep you for life.

      Sort of like traveling.


      Link Reply
  • Paris Apartments January 25, 2011, 4:57 am

    I agree with you Wade. Once you are caught by the sailing bug, you will never be the same again. It is a fabulous lifestyle and if you can afford a totally free way to live and experience the world.

    Link Reply
  • Alex September 19, 2013, 9:59 pm

    Sailing is one of the most relaxing activities in the world, while being a very exhilarating one at the same time. What kinds of boats did you use?

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