North Oak Island

As a charter captain, I always ran this channel on the way to Devils Island—for many reasons, but mainly because it was the fastest way to get out of sight of the mainland. That way, no matter where someone pointed and asked, “What island is that?” I could always name an island—never had to admit we were still looking at the mainland.

But beyond the trick, Oak Island itself is worth the route. It has one of the most diverse and dramatic shorelines in the Apostles, with the highest elevation of any island. From up close or even far off, its hills and valleys give it a tropical, almost Caribbean look—at least to me.

And if you were ever lucky enough to be on a tour with me, you may have seen “My Cave.” It’s right here. This year, though, the water is low and the guarding rocks look sketchy. If I brought you in before, it was probably on The Rendezvous, our shallow-draft catamaran. I wouldn’t risk it now with a V-hull sterndrive.