Set Sail Superior
Posted on: January 1, 2021
Ryan Asher Benjamin on a dock

Three fellows set sail on Lake Superior earlier this year. Here is an interview with Ryan Asher Benjamin, one of the “sailors” as he’d put it about their adventure.

When was your trip?

Nik, Evan and I began our trip aboard Ol’Miss B’Haven in Midland (Lake Huron) on August 15th, and arrived in Thunder Bay on September 16th. So we were gone for a total of 32 days, although we didn’t sail everyday. 

Where did you go?

We decided to follow relatively close to the shore for most of the trip. This way we could anchor every night, explore the coastline on foot and swim to shore in case of…you know. We anchored in mostly remote areas, but enjoyed the odd port in Killarney, Spanish, Blind River, The Soo, and Rossport. Lake Superior was definitely a different beast than Huron. Long stretches of remoteness and exposure to big open waters woke us up quickly to the severity sailing can possess. We had to hunker down during a burly storm in Wawa for 10 days waiting for our weather window to tackle the Pukaskwa Coast. We were lucky enough to know some of the generous folks at Naturally Superior Adventures who helped us with a place to stay and warm meals in exchange for some wood chopping and boat repair work. We made sure to warm up in some saunas on the North Shore on our final leg of the trip at Caribou and Porphyry Island. 

How long did it take you to plan the trip?

Well, the plan was to get Thunder Bay. I think that’s all we really knew. Sailing cruising is so dependent on the winds, comfort level of the team, and of course how much gas is left in the jerry can, so it was hard to create a plan solid enough to follow. We had a rough idea of where we needed to stop (stock up on food and gas) and where we wanted to stop (saunas, shipwrecks and friends along the way), but for the most part we would plan our next day’s route the night before over dinner and rum punches. 

What was your sailing experience going into the trip?

Haha…none. You might be thinking to yourself: “Well, if Ryan had no experience than the other two aboard Ol’ Miss B’Haven were probably Jack Sparrow level sailors.” You’re wrong. None of us had sailing experience. We do now though, need not worry. 

What were some challenges you faced?

Oh boy, where to start. Things break all the time, you lose stuff overboard, fishing line gets caught in the propeller, everything from cooking to changing clothes is a team effort and people discourage you from going or worse, to turn back. Aside from the actual challenge of learning how to get the boat to move forward, left and right (aka sailing), the intrinsic characteristics of the trip were the main challenges. We, inexperienced “sailors”, were sailing a 21-foot swing keel sailboat AGAINST prevailing winds. For the non-sailors that means a f*cking small boat that rocks a lot and has to fight the wind constantly to make progress. Mild winds and/or waves could capsize us if we weren’t careful so we really had to pick our days and take full advantage of an east or south wind. Our sails ripped on our crossing from Pointe au Baril to Killarney and we had to spend hours sewing them back up to sailing standard, not a fun job. 

What are the highlights from the trip?

This may sound cheesy, but the people we met along the way. 

Let me paint a picture for you. You are 60-years old and have been sailing your entire life, you have finally bought the boat of your dreams; a 46-foot cruiser with all the modern amenities you’d ever need. You and your spouse can adventurously sail across Lake Huron during the summer months to escape amid the global pandemic. As you casually pull into the North Channel, one of the most renowned cruising destinations in the world, you notice a tiny vessel docked between boats that look more like yours. You approach it, hearing the sounds of guitar picking and mushrooms frying. To your surprise there are three young, scruffy lads crammed into the boat claiming that they are sailing to Thunder Bay and have already made it this far with no experience. They have no paper nautical charts, crappy rain jackets, a meagre 5hp motor, and a lot of eagerness. You can’t help but feel a little worried, jealous and curious. You have two options, tell them they are reckless and to turn back or respect the mission, share drinks and equipment and offer them every piece of knowledge you’ve gained throughout your years.

The folks who chose the latter route, were what made this trip so special. Sailing on the great lakes has become somewhat elite, set up for older sailors who have money. For some, our trip was idiotic, for others, refreshing. I can’t begin to express how comforting and reassuring it was to meet people who, amid a pandemic, were willing to lend a helping hand and offer their generosity.

Watching the Sleeping Giant form over the horizon was one of the most profound things any of us had seen, an unmistakable symbol that we were almost home. Oh, and watching the northern lights dance over the lake on our last night of the trip at Porphyry Island was pretty cool too.

Did your trip change your connection to the lake? If yes, how so?

Absolutely. I’m a recent graduate of Outdoor Recreation and Natural Science and last summer I worked for Parks Canada with the Lake Superior National Marine Conservation Area. As a student, my relationship with the lake was mostly for study – more of an abstract entity that was viewed from afar. With Parks Canada I deepened my connection with Lake Superior as an incredibly valuable resource teeming with history. I learned a lot about the lake and ways to actively appreciate and share it’s magnificence with people on the North Shore. However, this sailing trip was the first time I truly got to play on and experience the immensity and ferociousness of the lake. I’ve driven on the highway and flown to Southern Ontario countless times, but arriving powered by the winds along Lake Superior was by far the most connected and mindful way to travel. I recognized the true size of the lake, developed an even greater appreciation for the people who’ve lived and traveled along Lake Superior’s shores for millennia, the land is rugged and the water is vast. I have a special appreciation for Lake Superior and the beauty that surrounds it, and this trip helped solidify the lake’s wonder in my mind forever.

Do you have any advice for people wanting to get into sailing?

Sailing can be one of the most rewarding ways to travel and can be  incredibly meditative. I, by no means, am an expert but I know this trip is a stepping stone to longer and abroad sailing expeditions. I strongly encourage everyone who wants to sail to go for it, don’t let a culture of elitism in outdoor recreation stop you from going for a sailing trip. There are so many good resources online and sailing handbooks that taught me most of what I know now about sailing. For racing experience, the Thunder Bay Yacht Club at the marina offers the opportunity to anyone to join a crew to help during the evening race. I’ve crewed on raceboats a couple of times since the trip and found it to be very helpful in getting to know the boat, terminology and sailing principles. I would definitely recommend crewing on several different boats before going out and buying one to set sail on a long voyage. Recently I’ve been looking online to join a crew for a Pacific Island hopping trip on websites like and other workaway sites. Either way, the feeling of travelling a long distance powered by forces of nature is a remarkable thing that should be experienced by all at some point!

Ryan is working on a short film that documents the journey the three “sailors” took this summer.

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