Overnight Sea Kayaking Along the Maine Island Trail

Photography by Joe Klementovich

An adventure, no matter how near or far, needs three things to carve out its place in your memory.

On a rainy day like this one — when the wet, salty air rushes into my lungs and whisks me back in time, I am vividly transported back to one adventure in particular. A local adventure that checked off all the boxes and then some.

Lost coves make for perfect campsites along the Maine Island Trail.

First and foremost, there was intrigue and mystery. I know, perhaps that’s a bit hokey, but the months I spent researching an overnight paddle trip out to Jewell Island had conjured images of a Northern Atlantic utopia.

There were also stories — urban legends, really — of pirates, buried treasure (mhmm), smugglers, and the ghosts of wayfarers who had touched down on Jewell years ago.

Intrigue? Mystery? Oh, yes.

Second, it has a natural beauty that inspires a sense of wonder and awe. The adjectives most often used to describe Jewell are superlatives like “outstanding” and “incredible”, and even one account that claimed it was, “like Narnia”. To be fair, even the most humble adventures can leave you awe-inspired, and you don’t always need to take a trip of epic proportions to uncover a deep appreciation for nature. However, Jewell’s wild and lush island landscape will certainly do the trick.

Friends are the color of every adventure.

To round it all out, having a stellar crew of adventure partners to share the experience with is what makes it a truly unforgettable experience.

And on one sunny morning, I found myself standing near the shoreline of the East End Beach in Portland with a proper adventure ahead of me and my three comrades as we geared up for a multi-day paddle trip along the Maine Island Trail to our destination: Jewell Island.

While surrounded by piles of NEMO camping gear and four brightly-colored sea kayaks, we chatted excitedly, stuffing drybags full of food, supplies, and camera gear beneath the hatches in a real-life game of Tetris. It was only 8 AM, but the sweat began to bead up on my forehead and I searched for my sunscreen, hat, and water bottle — it would be a long day in the sun.

Navigating the Island Trail required a new set of skills for this longtime backpacker.

The Way to Jewell Island

Getting to Jewell’s mythical shores from Portland requires an eight-mile-long paddle along the watery path of the Maine Island Trail.

Yes, there are water taxis that will take you there, but a human-powered adventure is simply way more fun. It’s also a reasonably challenging journey. Good stamina, self-rescue skills, and general knowledge of kayaking are essential. Then, there are also the things that are out of your control, like maritime weather and sketchy boat traffic — oh, and fog. Fog is bad. Full stop.

As a lifelong hiker and backpacker, I’ve grown accustomed to relying on colorful blazes and trailhead kiosks to help me find my way. But I knew I wouldn’t find those here. With buoys as my waypoints and some secondhand knowledge from the experts at MITA and Portland Paddle, I was nervous and excited to put my navigation skills to the test.

Waking up with the ocean and a kayak by your tent offered endless opportunities rich in adventure.

To my surprise, it was fairly easy to stay the course — even though I had studied and researched the route ad nauseam. We intuitively zigged and zagged between the islands and channels that guide you out to where Jewell sits on the borders of where the protected waters of Casco Bay meets the open ocean.

At mile four, we hopped out of our kayaks at Little Chebeague Island to replenish our energy reserves, stretch our legs, and marvel at our surroundings. In case things don’t go according to plan, this is also a great option for an overnighter.

Then, during the final leg, something magical happened.

Not only had we exited the channel into the sparkling blue open waters, but at some point, we realized we had a fifth member. The head of a curious seal materialized on the surface near my boat and silently watched us. For the next half-mile, it trailed behind as if it were guiding us to shore. Maybe it was all that sun and saltwater, but I swore I made a friend that day.

Camping on a Maine coastal island — free from the sounds of civilization hustling only a few miles away.

Camping at Jewell

What they say is true. Jewell Island is like Narnia. The 221-acres are as spectacular as everyone claims. From the peaceful shelter of Cocktail Cove to the craggy shorelines and the winding trails that travel through the island’s forested interior, every square inch of it is breathtaking. Especially the mosquitoes, wow. Pro-tip: Do not forget the bug spray.

There are 12 first-come, first-serve campsites scattered along the perimeter of the island, and fortunately, we had snagged the best spot on the southernmost point. After a quick and easy setup, our oceanfront campsite was, without a doubt, as idyllic as I imagined. The area was quiet and secluded with an unobstructed view of the ocean as it stretched out in front of us. Plus, our early start left us with plenty of time to explore the shimmering coastline just before sundown.

The endlessly changing sky and water offered a dynamic backdrop — in every direction — to our exploration.

The indigo color of a pre-dusk sky transformed into an unforgettable light-show of pink, blue, and orange hues, and we savored our dinner while perched atop the rocks that looked out over Casco Bay. Once the sun had gone, a full moon emerged, shining brilliantly against the dark, and we spent the night gathered around our campfire, enjoying some good company, and cold beers that had survived the trip from Portland.

Nothing like sleeping after you've exhausted every ounce of your body

I fell asleep that night, tucked away in a cozy shelter, with that deliriously happy and tired-to-the-bone feeling that fills your cup for long after the adventure is over, and it’s especially nice on days when all you can do is recall one.

Our Kayaking Gear Checklist:

Katherine Englishman brings endless positivity into this world as a freelance writer and teacher of yoga and mindfulness to adults and children. She enjoys adventures of every season in the mountains of New England and on the coast of Maine with her husband, Brian, and their pup, Candy.