Pirate Sailing: Written by Ryan Deininger

September 2, 2014

For legal purposes, some of the names in this story have been changed.

For theatrical purposes, none of the events have been altered in any way. 


Walk the docks. That’s my advice to every single newbie in town. My second day in Ketchikan was spent meeting locals and swapping stories at the Asylum bar. It wasn’t long before a fisherman named John offered to show me around the docks by Berth #3. It was then, walking the docks, where I ran into Cap’n D for the first time. He was fixing up his newly-purchased-beautiful-in-a-Jaime-Lee-Pressly-sort-of-way 27ft sailboat. Turns out, we are both from Ohio and are massive Ohio State Buckeye fans. What I’m trying to tell you is this: Cap’n D quickly became my new best friend. This next story would have never happened if I hadn’t met John at the Asylum and decided it was a good idea to walk the docks with him. 


On July 1st, it was time to take Cap’n D’s sailboat out for her maiden voyage. A few friends came along for the ride: we’ll assign completely random roman numerals to identify the two women on board, let’s call them – V and M, the skipper – Cap’n D, resident journalist – Ryan (me), resident – Jason (another fearless editor of this publication). Our plan was simple: sail to Annette bay, drop off two passengers, and sail back. Easy enough. So we set out from the docks at approximately 7:30 pm. 


Actually, I failed to mention a few details that are pertinent to the story.

1) Cap’n D’s sailboat doesn’t have a water pump that circulates seawater through the diesel engine to cool it down – this means we have approximately five minutes (max) before the motor overheats for good.  2) His boat did not have AK registration numbers, rendering our boat an unregistered pirate ship the USCG would certainly have a problem with.  3) The mainsail was not attached to the halyard, a fact we discovered after shutting of the engine in the Tongass Narrows (thankfully Jason is 6’5” with a 7’ wingspan)  4) There is a wiring problem with the ignition. The only way to start the motor is by crawling down in the engine room and crossing the solenoid terminals with a screwdriver.  5) Only one of the two batteries on board is charged.  6) Not one single navigation light on the boat works… not a single one. She’s a beauty of a ship. She really is. 


The five of us motored into the Tongass Narrows and shut the motor off quickly to avoid overheating. We raised the mainsail after needing freakishly-tall Jason to retrieve the halyard from up high on the mast. Beautiful. We raised the Jib, argued over the correct way to cleat a halyard line (I deferred to V, our most experienced sailor), and cheered and toasted Cap’n D who skillfully manned the tiller and filled our sails with life. Everything looked great. Four of my best friends were there. The beer was there. The most beautiful sunset I’ve seen in Alaska was there. The wind was there. Until it wasn’t. 


About halfway down the West Channel (heading south to Annette Bay) the wind disappeared. Completely. Still high on adventure and friendship, we didn’t mind the new pace and enjoyed the adventure as the receding tide continued to slowly pull us toward our desired location. By the time we reached the south end of Pennock Island, it was 10:30 at night. I called my friend from Metlakatla and informed him that we would not be making our rendezvous. We looked for a place to anchor for the night. There was no chance of getting back to our dock before nightfall – bucking the tide with zero wind and zero motor was simply not possible. We had a few anchorages in mind and headed toward our first option. This is when we discovered 7) we didn’t have nearly enough anchor line to possibly anchor anywhere…. Hello nightfall. Hello Nichols Passage. We would have to sail until morning and do our best to ward of the rocks and exhaustion. 


M and Jason were the first to succumb to dreariness and at about 11:00 they decided it was bedtime. They crawled into their sleeping bags inside the cabin, trusting Cap’n D to keep them safe through the night. After passing Gravina Point, the ambient, swirling, frustrating wind of Nichols was enough to catch our sails and provided us with a bare-minimum of propulsion necessary for navigation. We eeked our way west through Nichols Passage as the last light of day faded away. The stars came out for about ten minutes until they disappeared behind rainclouds. Night really set in.


We passed the red light marking Walden Rock (don’t go near those rocks, if you’ve ever seen them at low tide you’ll know why) and the blue light marking the south end of Blank Island. We spotted a gigantic yacht anchored in Blank inlet and continued our progress west until even the lights of the yacht were out of sight. 


Then rain came. The winds came. With a sudden swing of the mainsail boom, a heavy gust caught the sails and keeled the boat over violently and lurched us forward. At about 1:00 in the morning we were finally sailing. The ocean became violent, the boat – eager to run for her first time – sang in the water as she split the waves with her bow. We threw our lifejackets on. V held firmly to the back of my vest each time I had to pee (which was often) over the starboard side. If any of us went in the water – there was no possible way we would be able to spot or maneuver the ship over to that unfortunate sole. Did I mention our boat had no navigation lights?


Ten minutes later it was gone. The wind anyways… the rain, apparently was there to stay. V was the next to heed the call of sleep and went below deck. Not much of anything was happening. We were bobbing on a glass pond with the lights of Metlakatla now in sight. At 2:00 in the morning it was too dark to even make out where the shorelines were. Our only guides were the distant lights of Met to the west and Ketchikan way off to the east. Cap’n D and I each grabbe3d another brew, cracked ‘em and lifted a toast to ourselves: to the two people that night who, I believe, were happier to be where they were than anyone else in the world. 


Before the last drops of cheap beer were finished, the wind decided to return with even more force than before. At 2:30 , with no navigation lights on the boat (just to reiterate, this is illegal and stupid… really freaking stupid), we hugged. We cheered. We raced from the storm. We flew. Through the torrents of rain and the howling wind, we took Cap’n D’s ship to the limits… and then we saw it. At about 8 knots, the rudder churned up the water creating a spectacular plume of phosphorescence in our wake. The water glowed creating a trail of blue flame 50 yards or so behind the vessel. 


We filled the sails and headed downwind toward the lights of Ketchikan. The blue phosphorous and lightning in the sky (a rarity here) followed our boat faithfully until we reached the West Channel again at about 3:00 in the morning. Then it happened again. The wind died. The rain stopped. Glass. The sky began to show hints of daylight. 


Cap’n D and your faithful author rode the tide in through the west channel. We traded spots at the tiller a few times. We fell asleep at the tiller few times. With no wind, all you can hope for is enough tide to allow the skipper to keep pointing the boat in the right direction. Remember – we can only use our motor for a few minutes at a time…. Even that much is a risk for permanent damage to the engine.; 


It took us three and a half hours to make it the 2 miles from the West Channel markers to our dock. Even then, being tired, soaked, freezing (a common theme since I’ve been here), and starving – we decided to start the motor and make a run at the dock. We started the motor about one minute too early. The engine failed about 100 yards from the dock. We drifted, hoping to get close enough for V and I to jump off and pull the boat in. We did. Barely.


And this is how I hope and intend to end many of my adventures here in Ketchikan: Barely.


Written by Ryan Deininger 



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