Explore More with a Group of Four
17 August, 2025
This was a big reason we moved here, after all.
Cristina and I have owned a 23-foot trailerable sailboat, or “trailer sailor,” for nearly a decade. This boat goes by the name Happy Life, and if you’re familiar with the common two-word lead-in to that phrase, you can pretty well figure out the inspiration for that moniker. You’ll also be able to identify who’s the captain of our little schooner, and who gets to be the navigator when he behaves.
As the relative newcomer to this hobby, I’m usually the skittish one anytime the winds pick up and the boat heels past 20 degrees or so. I’ve worked through some of my jitters, but I still tend to favor the leisurely approach out there. (We do this for fun, no?) The Captain knows when it’s time to take down the sail and thus guarantee herself more future sailing with me.
Oh, we’ve had our adventures. Cristina and I have been tossed and turned by a tumultuous lake many times on this boat – though most of those tosses have taken place on Lake Michigan, not its Superior counterpart where we sail today. Still, whenever I take to any of the Great Lakes, the haunting harmonies of Gordon Lightfoot are seldom far away.
On a recent weekend, Cristina and I were joined by Chloe and Artemis for our first actual overnight trip out to the Apostle Islands. The Apostles, a collection of 22 islands off the northern tip of Wisconsin, comprise a National Lakeshore managed by the National Park Service. As such, several of the islands boast an impressive network of docks, campsites, and trails. We’d been visiting for years, taking day trips out of the nearby town of Bayfield. Now we’re residents of that same town.
Our chosen destination that weekend was Stockton Island. Stockton is the largest and most developed of the Apostles outside of Madeline Island, a residential and resort locale that’s not part of the National Lakeshore. The island is shaped a bit like a handful of Play-Doh that’s been squeezed through a kindergartner’s fist, oozing between their fingers. At second glance, from overhead it more resembles a frog perched up on its front legs, ready to pounce eastward toward Michigan.
Cristina and I planned to overnight on our weekender boat (“a pop-up trailer with a mast,” as she describes it), with hopes of docking in the small harbor we’d read about. Given the size of our boat – and the comparative size of our travel companions – we decided to reserve a campsite at the adjacent campground as well.
After a couple hours under sail, we chugged into Presque Isle Bay and its tidy protected harbor. There we got an unexpected hand when we heard our names being shouted: “Cris!…Cris!…Erik!”
This startling hello was at once comforting and disorienting as we motored between piers – a wildly unexpected feeling 15 nautical miles from town.
Then we saw them: Bev and Mike, two of our new friends from the church we’d recently joined. Turns out they’d traveled to Stockton the previous day with Paul and Paula, another couple we knew from church, both in near-identical Cape Dory cruisers. Their two boats were docked end-to-end just inside the main pier. As we slowed our momentum just past the breakwater, they untethered the front boat and nudged it back a cleat, yielding just enough space at the end for the Happy Life.
After a raucous round of well-whattaya-knows and how-’bout-thats, we unpacked the camping gear for Chloe and Artemis and set off to find the campsite. That was where we would cook our dinner on the beach and play a board game through dusk, taking full advantage of the site’s west-facing position where we put the sun to bed.
I’m taking a brief sidebar here to describe the campground experience itself, because up until we arrived we’d had a frog of a time understanding what would await us at Stockton Island.
The recon we’d done suggested there would be little chance of scoring space at the dock. According to one of our books on the area, summer Saturday nights typically see as many as a couple dozen vessels anchored across the bay.
As for the campground, all we knew was that it boasted 20 reservable campsites strung like pearls up the inner leg of the frog. We could find no detailed campground map either online or in park brochures. Because of this, we arrived with little idea how easy the sites would be to access, how far apart they would be located, or how much privacy they would offer.
The boat question turned out to be a non-issue. Even if our friends hadn’t generously made space for us at the dock, the larger bay itself was less a spillover space for latecomers than a shallow and protected nook chosen by those accustomed to the anchor-and-dinghy scene. Indeed, some campers had simply anchored their boats offshore of the campsites they’d reserved, skipping the harbor area altogether.
This was a smart move, and likely the product of previous visits here, because the lineup of campsites actually stretched out for more than a mile. This was no KOA. Each site enjoyed approximately 75 yards of wooded distance from its neighbors. Our campsite, number 6, was not an unpleasant distance from the dock…but if you’d reserved campsite 17 with no ability or intention to anchor nearby offshore, then you had some real hiking ahead of you.
At least it’s a lovely trail.
People who regularly paddle or sail Lake Superior often refer to it as the “boss.” As in, you need to listen to the boss and heed the boss, because boss lake delivers some truly mercurial moods.
Well, this particular day must have been International Boss’s Day – because by late morning she gave the impression of being several martinis into her celebratory lunch. The lake was a placid puddle; there was utterly no wind to speak of. Had we needed to put up our sails to get around, we would have just sat there like a forgotten olive on a toothpick.
Our charts suggested there were sea caves positioned on the northeast edge of the island, near the bulbous throat of the frog. Cristina said she wanted to motor around the peninsula and investigate the caves – and, with nothing more important impelling us home, I was fine to continue our excursion out that way.
This turned out to be an inspired decision. Our Sunday became the highlight of the weekend.
At the first sign of sea caves, we ducked the Happy Life into a shallow bay and anchored in 15 feet of water. Chloe and Artemis first took to the inflatable kayak we use as our dinghy. They paddled to that initial cave we saw, and then they paddled all the way through the cave. On their return, they told us of a waterfall lurking just on the other side.
The captain and I took our turn. We snaked through the same tiny gap in the rock, turned back, and then proceeded right past the sailboat itself. We weren’t done. In the next couple tiny bays, we encountered a larger waterfall yet, a notch canyon, another watery cave large enough to stand up in, and a tall sea stack (i.e., a towering little island calved from the main) called Balancing Rock. It might have felt like our own little discovery were it not for several other pleasure cruisers bobbing nearby.
We encouraged Chloe and Artemis to take the kayak for one last spin to see those sites. I then surprised Cristina by leaping into the frigid lake to experience the sensation of a midsummer polar plunge. The water of Lake Superior here was so clear and blue that, aside from the bracing temperature, this whole northern Wisconsin scene had a real Caribbean flavor to it.
Following a brief no-martini lunch, I was ready to turn us around to the south on our way back to Bayfield. The other three reviewed the map and encouraged us to loop around the north instead. “Honestly, the distance is six of one, a half-dozen of the other,” Chloe said. “We’re already out here. Let’s see the part of the island we haven’t seen yet.”
Well, I’m the only one who saw much of that part of the island. I fired up our sailboat-adequate 6-hp outboard and proceeded to enjoy a near-silent three-hour putter back to the marina as each of my companions dozed in the afternoon sun.
To reiterate, my ambition that weekend was to sail no farther than the harbor inside the frog’s armpit. So when Cristina awoke from the slumber of a happy wife, I shared an admission.
“To be honest, if not for you I wouldn’t have rounded the corner to see the caves. I would have been happy to just head back toward town.”
She appreciated the comment. And she picked it up from there.
“Well, also to be honest…” she admitted, “if not for Chloe and Artemis, I probably wouldn’t have suggested exploring the caves in the kayak. I don’t think I would have been comfortable leaving the boat anchored on its own.”
And herein it hit me the real gift of exploring the outdoors with others.
When we’re exploring by ourselves, we’re free to see the sights we want to see and keep the pace we would set. It can be a joy to move about the woods and water independently.
We’re also prone to play it safe. We’re incented to stay within ourselves and our abilities, knowing if we take things a little too far, we can wind up injured, lost, or marooned. We could find ourselves starring in our very own private filming of 127 Hours.
Exploring with just one other person enables us to go a little further. That person can lend us a hand if we fall, or they can go for go for help if we do more than just fall. They can share the load of essential gear to carry. They provide cover if we encounter the unknown, and they can look out for our belongings if we need to leave them for a time. Travel with more people yet, and we can conquer mountains.
Companions provide not only ease of travel. They provide ease of mind as well.
After all, you can’t expect friends from church to just appear out of nowhere.
© Erik Lien
Erik Lien 
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