Superior Sailing

Just as we were about to ease into a quiet evening at anchor in Presque Isle Bay, on the south side of Wisconsin’s Stockton Island, the crowd rushed in. The procession of cruising sailboats resembled a busy airport with planes lined up miles to leeward of the main runway. We watched as the cruisers came from all over the Apostle Islands and dropped into formation, motoring one by one into the

Just as we were about to ease into a quiet evening at anchor in Presque Isle Bay, on the south side of Wisconsin’s Stockton Island, the crowd rushed in. The procession of cruising sailboats resembled a busy airport with planes lined up miles to leeward of the main runway. We watched as the cruisers came from all over the Apostle Islands and dropped into formation, motoring one by one into the protected anchorage. The evening air was warm, the northeast wind soft. At 65 degrees, the clear fresh water was considered toasty for western Lake Superior in August. This was the place to be, and apparently every sailor in the Apostles knew it.

In a matter of minutes Presque Isle Bay’s boat population would triple. One at a time the keelboats maneuvered along the bay’s shoreline. With minimal conversation on board about where to drop anchor, each boat picked its spot, lowered the hook, backed down hard to sink the anchor deep into the sandy bottom, and cut the engine. All of this was done swiftly and in an order that later, in the dark of night, would appear choreographed; two rows of masthead lights lined up evenly like opposing streetlamps. Then our fellow cruisers swam in the lake, handed out rounds of sundowners, and fired up their barbeques.

Sarah and I witnessed all this from the comfort of the cockpit on Golden Sun, a Crealock 34 from Superior Charters in Bayfield, Wisconsin. We were two days into a week-long cruise of the Apostle Islands, a largely undeveloped area managed by the National Park Service and known for, among other things, its unique assortment of 19th-century lighthouses. The Apostle Islands National Lakeshore is a compact 21-island chain located off Bayfield, Wisconsin, a cozy sailing town that has more sailboats than year-round residents (611). “Escape” is an appropriate description of the Apostles. You escape to the Apostles to bask in the natural beauty of thick woodlands, sandy shorelines, and crystal-clear lakewater. You can explore some of the lighthouses, chase the echoes of your voice inside sandstone caves, and enjoy crowd-free cruising. The “crowd” around us at Stockton peaked at fewer than 20 boats. This was in the area’s most popular anchorage during the height of the cruising season.

Some years the weather window on Lake Superior barely cracks open. It can be a burly marine environment, even in summer. Tall tales of cold Canadian air, frigid water, and high winds add to Superior’s lore. The area’s landmark caves are scars from centuries of pounding northeasters and shifting ice. That sailboats tend to be large in Bayfield suggests the locals have found protection from the elements in their long waterlines. Books have been written about Superior weather. From our vantage point at Stockton Island, we saw only beauty. But we were knocking on the boat’s brightwork with every radio forecast, knowing that if the week’s pleasant forecast held, our mammoth bag of rain gear and warm clothes would remain zipped and the decks would hardly get wet.

The day ended with our own routine. We took one more halyard swing into the lake, bathed with some sweet-smelling biodegradable soap, and thought about the next day, sundowners in hand. Then, as the sun slipped behind Bayfield, we remembered we didn’t want to think much this week. The next day we’d explore Stockton’s hiking trails, pick blueberries, search for black bears, and go sailing.
We weren’t actively searching for bears at Stockton, but our fascination with (or fear of) meeting up with a live one started long before the cruise began. “Can bears swim?” Sarah asked. I rolled my eyes in a weak attempt to dismiss the thought of a fuzzy-wuzzy climbing up our stern ladder late at night. “That’s a legitimate question,” she insisted.

Indeed it was. Bears swam from the mainland and populated the Apostle Islands. Stockton once had a pet bear, Skar (named for his patch of missing fur). He was popular and friendly with cruisers, probably too friendly. People started feeding him, he grew comfortable with humans, and eventually they had to put him down. We met a stuffed version of Skar at the visitors’ center on Stockton.

Stockton has two black bears per square mile—an alarming statistic for an island that welcomes more than 100,000 visitors every year. Our chance to see one came and went as Sarah and I ran around the trail past Julian Bay, an excellent anchorage in a west or north wind, through densely wooded areas, and along the Presque Isle Bay shore. We made it back to Golden Sun without incident.

Before continuing on a counter-clockwise tour of the Apostles, we ended our stay at Stockton with a visit to the blueberry bushes in Julian Bay. To get to the berries, you cross Julian’s singing beach—drag your feet to hear the sand screech—and walk along the edge of the bay’s aqua water. The berries are small bursts of flavor. There were enough to fill up the Crealock’s bilges, if we wanted to. Instead, a half-hour berry-picking session produced enough fruit for the week’s breakfasts and a few bellyaches from overconsumption.

Our route would eventually take us to the sandstone caves on the outer islands. So far we’d been refreshed at Stockton and entertained on Madeline Island, where we followed advice from a Bayfield resident to visit Tom’s Burned Down Caf. The outdoor bar, thrice burned to the ground, is now partially covered by a tent and colorfully decorated with flea-market junk, license plates, and inspirational remarks scribbled on wooden tablets (“If at first you don’t succeed, try lowering your standards”). We saddled up to the bar, listened to the band’s offerings, and amused ourselves reading the wall. Madeline is the only inhabited island in the Apostles. A ferry transports cars and people along the short route we sailed from Bayfield. It runs until the water freezes—around October—at which point locals drive the state-monitored “ice road” to Madeline.

We left Stockton in a faint north wind and coasted in the direction of Raspberry Island. Flying every square foot of Golden Sun’s tanbark sails, we enjoyed a lazy afternoon sail in the hot sun. Several fleets of sea kayaks kept us company en route to Raspberry. Once there, we tucked into a sheltered cove near a trailhead that leads to the island’s lighthouse. At one time Raspberry had a small community that serviced the light and its fog horn. An old warehouse, a few houses, and a privy are still standing. Much effort has gone into supporting the island’s eroding bluff, which has moved dangerously close to the light. We were surprised to find a croquet game set up in the field for visitors. At the end of an amusing match in the thick grass, we heard thunder rumbling in the sky and headed back down the trail to the boat.

The next morning we pulled up the anchor and started early on a long day of sailing that would take us to the caves of Devils Island and eventually to Sand Island. We arrived at an anchorage off Devils’s northeast corner in time for lunch, a noisy affair with waves crashing inside the caves in the background. It was easy to imagine Lake Superior waves, which build up over 300 miles of fetch from the opposite shore in Canada, working like massive chisels on the soft sandstone cliffs at Devils. The waves sculpt the shoreline into red-and-brown apertures easily entered by boats. Being inside one is equal parts scary and fun.

At Sand Island we tucked into a well-protected anchorage on the island’s eastern shore, a tactical decision. Big west winds were forecast to arrive that night, putting an end to our tranquil cruise. At last we would get to see the rough-and-tumble side of Lake Superior, and admittedly I was looking forward to it. That night I retired with a book by Great Lakes sailor Marlin Bree. In Wake of the Green Storm, his book about surviving a storm with hurricane-force winds on July 4, 1999, in a small boat, Bree wrote; “Superior was not to be trusted, no matter what the forecast said.”

We awoke the next morning to 25-plus knots out of the west and a clear sky—beautiful conditions for sailing. Sarah and I hiked to the northern tip of Sand to visit its lighthouse. Earlier we had watched two small cruisers haul their anchors and head out under shortened sail. At the lighthouse we could see both boats laboring to weather, apparently headed to Duluth, Minnesota. They had a long day in front of them. Thankfully we would be headed the other way, back to Bayfield.

The French named the largest freshwater lake in the world Le Lac Superior—the upper lake—because of its location relative to the other Great Lakes. We could easily think of other reasons. Sarah steered as we ran along the shores of Raspberry and Oak islands. Golden Sun was in her element and felt solid in the oceanlike conditions she was designed for. But we still felt small in the heavy weather, and not just because it was windy. Our surroundings felt superior in scale. The thick tree cover on Oak Island and in Raspberry Bay on the mainland towered high into the sky. Puffy white clouds appeared to be in another orbit.

We turned the corner at Basswood Island and trimmed in hard for Port Superior Marina, home of Superior Charters. We were pushing the boat now and probably should have reefed. We got a bit thrashed in the puffs and chilled by the spray coming over the sides, which felt good, like some sort of initiation to the lake. Back at the dock, Sarah and I both felt conflicted—satisfied with such a great day of sailing and disappointed the cruise was coming to an end. Then we thought about the pair of small cruisers sailing straight into the heavy weather on Lake Superior. We had had a taste of it, and with more weather on the way, our timing seemed just right.

At A Glance

Destination: The Apostle Islands

When to go: Although many locals sail in late spring and early fall, the true sailing season in the Apostle Islands is June through August. Weather varies significantly. Summers can be cool with air temperatures in the 50s and 60s; water temperature in June can be as cold as 48F.

It always pays to keep an eye on the weather in the Great Lakes. Thunderstorms move quickly and aren’t always forecasted.

Bayfield: In the June 2004 issue of SAIL, Bayfield was recognized as one of the 10 best places to sail in the U.S. It has the right combination of good sailing conditions, a unique cruising ground, and an excellent sailing community. The number of registered sailboats is considerably higher than its population of 611. The locals live for summer, when the population swells.

Charter company: Superior Charters, Bayfield, WI; 800-772-5124,



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