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Lake Superior’s Apostle Islands: A Schoolhouse for Sailors

Captain Mike Simon stands watch off Stockton Island on the Breeze, a 33-foot teaching sailboat managed by Superior Charters. Photo Brian E. Clark

By Brian E. Clark

It’s about a dozen miles as the crow flies from the village of Bayfield, WI to Stockton Island in the southwest section of Lake Superior.

But on a recent three-day sailing trip in this extraordinarily beautiful corner of North America, my ski patrol buddy, Dave Cushman, and I were taking the long route as we tacked back and forth on our 33-foot vessel, the Breeze, with Captain Mike Simon of Superior Charters.

By the time we reached Presque Isle Bay – our anchorage for the night – we’d logged more than 25 miles, zigzagging past Basswood, Hermit and Madeline Islands. In the process, Cushman and I had netted bushels of valuable sailing experience that will allow us to charter our own sailboat later this summer.

Adding to our adventure, we celebrated on water and ashore, the 50th anniversary of the Apostle Islands National Lakeshore. Advocated by former Wisconsin Gov. Gaylord Nelson, a visionary conservationist who later served as a U.S. Senator, 22 islands in the Apostles’ archipelago were added to the National Park System in 1970. Nelson was also the man behind the establishment of Earth Day.


Brian E. Clark pilots the Breeze, a 33-foot sailboat out of the Pike’s Bay Marina. Photo Dave Cushman.


I’d sailed in the Apostles – often called a freshwater version of the Caribbean’s British Virgin Islands – eight years ago when San Francisco-based photographer Moth Lorenzen and I booked a 44-foot sailboat through Superior Charters.

With our young families in tow – four children ages six to 12 and our respective spouses – Lorenzen captained the boat and I took orders as the second in command. (There was no third officer.) We explored the archipelago, hiked and jumped in and out of the lake’s chilly waters for four days before turning in our sailboat and taking a short ferry ride to Madeline Island – a popular tourist destination that isn’t part of the National Lakeshore, though it is home to a big state park.

I followed Lorenzen’s orders raising and lowering the sails during the trip – and managed to keep my head from being clobbered by the boom – but I never quite understood how the boat sailed or even what some of the terms meant.  So when the opportunity arose this early summer to take a class, I jumped on it. Better yet, Cushman – who grew up sailing in Lake Michigan – signed on to join me.

We drove north from Wisconsin that first night. After buying provisions, we bunked on the Breeze, our home for the next few days.

We met Simon the following morning, carefully motored the boat out of the Pike’s Bay Marina and headed into the open waters of Lake Superior.  We soon raised the mainsail and then the jib sail at the bow of the boat.


A sign on Stockton Island in the Apostle Islands explains some of the highlights of the National Lakeshore. Photo Brian E. Clark


I learned that sailboats only “catch” the wind for propulsion when they are headed downwind. The rest of the time, a sail essentially functions as an airplane wing standing on end. That means when the sails are trimmed or adjusted correctly, each sail’s leading edge points into the wind, creating higher pressure on the windward side (the side facing the wind) and lower pressure on the leeward side (the side away from the wind), actually lifting the boat forward. It took a bit of time for me to wrap my brain around this concept, but eventually, I got it.


Sunset over the Pike’s Bay Marina near the Apostle Islands National Lakeshore in the southwest corner of Lake Superior. Photo Brian E. Clark



Cushman and I shared time at the helm of the Breeze, doing our best to make the boat sail smoothly. We also practiced anchoring and docking the boat safely, a key skill to learn if you want to return a chartered boat worth $150,000 back to its owners undamaged. Under Simon’s watchful eye, we successfully returned the boat to the marina unscathed.

That late afternoon, Cushman and I ate dinner in Bayfield at Gruenke’s Restaurant. With pandemic restrictions, we ordered take-out and sat near the marina watching boats of all shapes and sizes on the lake and children playing on a public lawn.

When we arrived back at Pike’s Bay Marina – about 2.5 miles south of Bayfield – we were invited for a cocktail by a friendly couple on a boat one slip down from the Breeze. As I drifted off to sleep in my berth in the bow of the Breeze, I told myself that I could get used the yachting life.


Captain Mike Simon arrives for a three-day sailing course on the Breeze, a 33-foot sailboat managed by Superior Charters. Photo Brian E. Clark


Simon arrived the next morning bright-eyed around 9 a.m. We began our voyage to Presque Isle Bay on 10,054-acre Stockton Island, the second-largest landmass in the archipelago after Madeline Island – which has a similar shape to Manhattan, but only a few hundred residents.


Lady Slipper flowers sparkle on Stockton Island in the midst of the Apostle Islands National Lakeshore in the southwest corner of Lake Superior. Photo Brian E. Clark



We sailed into a northeast wind on a crooked, tacking course, arriving at our destination around 4 p.m. and again practiced our anchoring skills. Later, Cushman and I rowed our dinghy to a sandy beach and hiked past lovely displays of blue-bearded lilies, lady slippers, lupines and ferns, as well as trees bent into magical shapes.

Once we reached the visitors’ center  – sadly closed because of the pandemic – we continued on to Julian Bay, where the beach is known for its singing (squeaking) sands. Sandhill cranes and loons serenaded our walk. Black bears are also abundant on Stockton Island and we considered ourselves lucky that we didn’t encounter any.

The winds were whipping up whitecaps on Julian Bay, so we didn’t stay long before returning through the forest to our boat.

That night, Cushman made a delicious meal in the Breeze’s galley of pasta covered with tomato/ground turkey sauce, plus sourdough bread and a mixed salad. We topped that off with a local beer and watched the sun set over the islands.

Sailing student Dave Cushman and Captain Mike Simon enjoy a late afternoon on the Breeze sailboat in Presque Isle Bay off Stockton Island. Photo Brian E. Clark.


During dinner, Simon told us of his sailing adventures, which included running trips from the Florida Keys to the Dry Tortugas and racing in the Atlantic and Pacific oceans, as well as the Gulf of Mexico. He first visited the Apostles in 200- and quickly fell in love with the archipelago. His home now is near Bayfield and he said he’s more than content.

“I’d read magazine articles about this area being one of the top spots to sail in the country and they were right,” he explained. “I was hooked soon after I got here. The natural beauty of the forests, the rocky islands and the caves carved by the big waves of Lake Superior really appealed to me.

He also said he appreciates his “office.”

“When I wake up every morning, the first thing I see is Lake Superior, whether I’m on a boat or in my bedroom,” he said with a big smile.  “From my vantage point, I can also see  Madeline Island and Michigan’s Upper Peninsula.”

We slept in a bit the next morning and with the wind blowing again from the northeast, we navigated a relatively straight shot downwind to the marina, practicing our docking skills a time or two before we pulled the Breeze into our slip for a thorough cleaning by Cushman and myself – which is also required when you charter a boat.

There were no keys to turn in, but before we bid goodbye to Simon and the Superior Charters’ staff, we told them to save a boat for us in late August or September. We knew for certain we’d be back.

For information on other things to see and do in and around Bayfield, which bills itself as the “gateway to the Apostles,” see bayfield.com.


Brian E. Clark

Brian E. Clark is a Madison, Wisconsin-based writer and photographer who contributes to the Chicago Tribune and LA Times on a regular basis. He also writes a weekly travel column for the Milwaukee Journal-Sentinel.  A native of Iowa, Clark is a University of Colorado, Boulder, graduate who focuses on adventure travel. He’s a veteran whitewater kayaker and skier who has lived in Norway, Sweden, Brazil and Bolivia. He worked for newspapers in Washington State and California for 25 years, including the San Diego Union-Tribune, before returning to the Midwest. He manages to head back West several times a year when he’s not off in other corners of the globe. Or poking around Wisconsin.

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