Do you have a favorite island?
It’s been a while since I’ve guided day trips regularly. The grind of arriving at the shop with a rapidly cooling coffee, tying up boats, sunscreening my face and hands, checking the paddler list, forgetting what I read checking again. Memorizing the names in the group circle, remembering them for a half hour, forgetting them again.
What do you do in the winter? How many days of the week are you out here? Oh, mostly guide overnights these days, so I’m not actually here here much. How many islands are there? Do you have a favorite?
I do have a favorite island. I actually have a lot of favorites really. I think Sand Island makes for a really fulfilling one-night trip. Devil’s Island, of course, feels like stepping into a Dr. Seuss book with it’s cathedral-like caves, thick carpets of moss and large owls darting in and out of it’s spikey trees. Outer Island feels like the moon to me. Oak Island like Jurassic Park. Basswood Island makes for a unique adventure trip, the sort you don’t find in guidebooks and I like that too.
But my favorite is Bear Island.
Bear Island is a four and a half mile crossing from York Island or two miles from Raspberry. In the past two years, I’ve had some of my most exciting days on the water here and some of the most beautiful. It’s the natural jumping off point to Devil’s Island, and along the path to Rocky Island, a popular campsite for group trips.
On the exposed Northeast end of the island, you can find blocky red sea caves that feel like the absolute edge of the earth. In the southeast, there’s a sandspit with crystal clear water for swimming, one of the best lunch beaches in the islands.
Working in the outdoors and in travel, I feel like I have so often been told “at some point you’ll have to come back to the real world”. To me, Bear Island is one of the places in the world that feels the most real —
Swimming in the clear water of the sandspit. Lounging on the beach at the north end of the island. Paddling through the caves and under the cliffs looking out across the water at the North Shore all of that icy cold water between you and Silver Bay.
It always strikes me that if I were here five hundred years ago it would look both the same and drastically different, centuries having eroded out entirely different caves but the bones of it still the same, still remarkably similar to a pre-industrial world.
Devil’s Island is a destination, Sand Island frequented by outfitters and kayak trekkers. Bear Island is often overlooked, neither the largest caves nor the most intricate, a stepping stone on the way to Devil’s but not generally a destination in itself.
It’s on the map but off the radar — you won’t find viral videos about Bear Island, just a few scattered images. Out here, I’ve only ever run into one other group. Mostly it’s just sailboats passing in the distance.
So how can you get out there?
Bear Island isn’t an easy kayaking destination by any stretch of the imagination. Of the two overnight trips I’ve guided out this way, the first had a real capsize and rescue and the second had some pretty serious inline towing to make it back to mainland in shifting winds.
If you can’t picture what that might look like and how you would execute those rescues, best book a guided overnight kayak tour (link to the outfitter I work at! I will likely not be your guide; I only do custom women’s overnights now and help out in the office). In order to get out to Bear Island, you’ll likely need a 4+ day trip — longer maximizes your chances of a good paddling day. If guided isn’t your jam and you’re ready to learn some kayak skills and rescues for yourself, boy do I have an idea for you…
Want to learn to sea kayak this summer!?
While I work as an outdoor guide and spend upwards of 50 nights camping a year today, I actually didn’t grow up outdoorsy. It wasn’t until college that I realized I wanted my life to look a little different than I’d previously thought and I took a chance and applied for a kayak guide job up on Lake Superior with literally no experience.
It would be an understatement to say that sea kayaking changed the course of my life. Beyond the absolute magic of being able to experience places virtually unreachable by any other mode of transport, sea kayaking has built up my confidence and changed the way I interact with the world. There is honestly no feeling like looking out at a channel of whitecap-strewn waves and looking at the people behind you and saying “don’t worry, I’ve got this” and meaning it with your whole chest.
If you’ve been looking for something new, challenging and confidence-building to try out, come join the Freshwater Paddler Symposium this June 25-28. The new schedule for this year just went live and this is a great way to learn about sea kayaking, get one-on-one instruction to learn as much as possible quickly, experience Lake Superior and hang out with a community of paddle-minded folks!
I’ll be facilitating a women’s beginner group! If you’d like to join us, first register here, then reserve a rental sea kayak kit with Lost Creek Adventures or Trek & Trail, then shoot me an email and I’ll add you to the group chat so you can join the group camp and meet some rad ladies!
Nice piece. Had to look up Bear Island to see if it was in Michigan, Wisconsin, Minnesota or Ontario. Looks like an incredible place to visit.
A beautiful retreat from daily life. Thanks for sharing.