Apostle Islands Sailing Charter

A charter vacation in these remote islands in Lake Superior was just the sailing fix this west coast couple needed.

April 7, 2021
Stockton Island beaches
At 7.5 miles long and 2.5 miles wide, Stockton Island is one of the largest islands in the group and offers several hiking trails and plenty of beaches to explore. John Guillote

I woke up with the sun and climbed into the cockpit with a blanket and a hot mug of coffee, breath steaming in the crisp morning air. The shoreline was luminous in the soft light, the empty beach alluring. The boat rocked gently in the breeze as an eagle called out from high above. I had to pinch myself; I was not in the San Juan Islands near Seattle or in the Gulf Islands of Canada. I was on Lake Superior in Wisconsin, a lake that both looked and acted very much like an ocean.

I am an ocean sailor. I learned to sail in the Pacific Northwest and left to go cruising from there, my sights pointed south and west. I had never been sailing on fresh water. When travel restrictions in response to the COVID-19 outbreak kept us from returning to our boat waiting for us in a boatyard in French Polynesia, my husband, John, and I looked around to get our sailing fix locally. We found it in the unlikeliest of places: right in the middle of the country.

The Apostle Islands is a grouping of 22 protected islands nestled in the corner of one of the biggest lakes in the world. “Lake” is a bit of a misnomer; “inland sea” is a more accurate description. This particular inland sea is the size of Austria and at places is over 1,200 feet deep. It has the largest surface area of any freshwater lake on Earth, over 31,000 square miles, and holds 10 percent of the entire planet’s fresh water. That’s crazy! It’s also hard to conceptualize because the entire sea is situated 600 feet above sea level. To reach the ocean, boats must sail 2,400 miles across three lakes and navigate 16 locks to descend those 600 feet.

Apostle Islands red sandstone sea caves
The Apostle Islands are renowned for dramatic red sandstone sea caves dotting the shores. John Guillote

I simply couldn’t imagine it: a lake like an ocean, a contained body of water capable of throwing challenging weather conditions to test even the most seasoned sailors. Unpredictable wind, sudden pea-soup fog, navigational hazards and steep wind waves are all common conditions. The rewards are just as sweet too. Secluded anchorages, stunning sunsets, vibrant contrasting colors of red sandstone, verdant green trees and clear blue water. I just had to see it for myself.

Superior Charters & Yacht Sales in Bayfield arranged for us to sail a Jeanneau 349, aptly named Bliss, for a four-day cruise through the Apostle Islands. These islands, along with the nearby mainland coast, make up a 70,000-acre National Lakeshore area. Only one of the islands is inhabited; the rest are home only to healthy populations of black bears, deer, eagles, otters and more. It was the beginning of September and the start of their shoulder season, which meant quiet anchorages, fewer bugs, cool crisp nights and unpredictable weather.

Bliss was well-appointed with a full galley, plenty of water and diesel, good sails, an anchor windlass and an autopilot. One of the benefits of chartering from Superior Charters & Yacht Sales is that they encourage guests to board the boat the night before the official start of the vacation. We picked up an envelope at 7 p.m. with a map of the marina, codes for the bathrooms and a checklist of items we should verify on the boat. That evening we introduced ourselves to Bliss, unpacked and settled in. It was a wonderful, stress-free way to start the vacation.

John Guillote takes the helm of Bliss
John Guillote takes the helm of Bliss, a Jeanneau 349. John Guillote

The next morning, checkout was a breeze. Mike, a captain with Superior Charters, arrived promptly at 0800 to review the checklist and answer questions. He ensured that we knew where everything was, what safety equipment we had and how to use the systems on board. He then revealed his love for this unique place as he bragged about the beauty of the islands and shared with us some of his favorite secluded spots.

By midmorning, we waved goodbye to Mike, slipped our dock lines and hoisted the sails in a sporty 15 to 20 knots from the southwest. The weather forecast kept us conservative in distance and anchorage choice that first night. The wind was predicted to make a 135-degree shift in the evening and blow a gale from the north all night. There are no all-weather anchorages in the Apostles, so one thing Capt. Mike coached us on was to always have a backup plan in case the winds decide to buck the forecaster’s predictions. We chose the southeast hook of Stockton Island, a popular choice judging by the six other boats in the bay, all nestled into the northern corner.

The forecast was not joking. Just as the sun dipped below the horizon, the wind made an about-face and started blowing from the north without lessening in intensity. A new boat in a new place in 35 to 40 knots of wind overnight is never a recipe for a good night’s sleep, but Bliss handled the weather like a champ. We got up to confirm our position and check the anchor rode for chafing a few times, all without incident. She held well in the sticky sand, the wind whistling harmlessly through the rigging.

The author works the windlass in the bow of Bliss.
The author works the windlass in the bow of Bliss. Shoulder-season cruising means many wide-open anchorages. John Guillote

A gale was an exciting way to start the trip, and a good reminder that shoulder-season sailing means being prepared for a variety of conditions. It was just like cruising in the San Juan Islands in September, when summer and winter collide overhead. A fresh breeze turns cheeks red; puffy jackets and beanies appear from the depths of lockers. It was so similar to sailing in the San Juans, in fact, that I kept watching for whale spouts in the distance!

We fell into a familiar routine. Our days started with an unhurried cup of coffee in the cockpit while listening to the weather forecast on the VHF. We would then haul the anchor and hoist the sails for a few hours of exploration. By late afternoon, we would set the hook in a new anchorage, with plenty of time to explore the shore by kayak or foot before happy hour. A glass of wine, a beautiful sunset, a big hearty dinner and a quiet evening with a good book. It felt so good to be back on the water.

The Apostle Islands are bunched together, which makes them easy and accessible for fun daysailing. While our conditions were not always (well, ever) a perfect 15 knots on the aft quarter, we never felt exposed or in danger. In fact, most of our time under sail was fully voluntary. We were never far from our next anchorage and would often take the meandering way, easily turning a 10-mile passage into a 30-mile sail that laced us through rocky outcroppings and along sandy shorelines.

The lighthouse tower on Devils Island.
The current lighthouse tower on Devils Island was erected in 1898. During the summer, the lighthouse is a popular stop for visitors. John Guillote

Each island in the Apostles has its own personality. Stockton has an intriguing mix of lakes, forests and wetlands. Wonderful hiking trails crisscross the island, often on raised boardwalks above the delicate grasses and swampland.

Oak Island is the tallest at 1,000 feet above sea level (and 400 feet above this sea’s level). It was the first Apostle island, emerging about 10,000 years ago as the level began to drop in a giant lake that had formed between the retreating glacier edge to the north and high ground to the south. Today Oak Island has steep cliffs that rise abruptly out of the sea and a very active black bear population.

Outer Island is the guardian, a sentinel standing tall in the northeast corner, with the other islands huddled behind it. It is this island that gets pummeled by the most vicious northeasterly gales. As evidence of its protective responsibility, the rugged coastline is dramatically pocked with sea caves where waves have battered the sandstone for thousands of years.

Madeline is the only populated island, with 302 full-time residents. The main street through town is dotted with a handful of tourist shops and restaurants, served by a quaint car ferry from Bayfield. It was particularly quiet when we arrived midweek and out of season, following an unstable and worrying summer. Only one restaurant was open, offering burgers and sandwiches for takeout only. The impact of the pandemic is most apparent in places like this, where the whole town relies on summer tourism. With a high season only 90 days long, even in a good year it is hard to stay sustained through the slow winter. This year, some shops and restaurants never opened at all.

The sailboat Bliss on Lake Superior
Lake Superior offers challenging and exciting sailing conditions, and Bliss handled them well. John Guillote

Too soon it was time to sail back to the marina. Or rather, motorsail; by then we had a wispy 6 knots from the northeast. The cruise had been just the antidote to my landlocked blues: a wonderful wilderness escape with no cell service or Wi-Fi, and few other people. It was four days of communing with the wind and waves, punctuated with visits to picturesque havens of sandstone and verdant conifers.

We only just got a taste. The crystal-clear water beckoned me for a swim, but the cold north wind dampened my enthusiasm to jump in. The leaves started to change while we were there, taunting me to come back and see the islands when they explode in color. And in winter, when conditions are just right, it’s possible to walk to some of the sea caves instead of sail. Icicles protrude from the caves, the whole scene still and quiet as if frozen in time. That is something I simply cannot imagine, and so I know I’ll be back.

Cruising the Apostle Islands

Bayfield, Wisconsin, is the home of Superior Charters and the Gateway to the Apostle Islands. The small town is located on the coast of Lake Superior and is about a 90-minute drive east from Duluth, Minnesota, which has an international airport.

Charter season: Late May through September, with the summer months being in greatest demand.

Guide Books: Superior Way by Bonnie Dahl and Sailing Adventures in the Apostle Islands by Lawrence W. Newman.

Provisioning: Grocery stores are available in Bayfield and nearby Washburn.

Fleet: Superior Charters’ current ­bareboat fleet comprises 26 monohulls and two catamarans.

Becca Guillote is a freelance writer and full-time sailor aboard Halcyon, a Valiant 40.


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