The Jewell of Casco Bay

Discovering the magic of Jewell Island on an overnight sea kayaking adventure along the Maine Island Trail

My arms are dead tired, and even the muscles of my legs have started talking. At mile seven, it has become clear that sea kayaking is a full-body workout, but the gentle sea breeze and spray of saltwater brings me some relief. More than anything, I feel energized by the lure of Jewell Island, a place I have heard so much about for so long.

It is just past noon, and our group of four is closing in on the last leg of the eight-mile-long paddle from Portland’s East End Beach to one of the most scenic stops along the 375-mile Maine Island Trail. Jewell sits on the fringes of Casco Bay—just far enough to be a demanding trek, but nothing that anyone with decent upper body strength, a bit of kayaking experience, and a sense of adventure can’t do.

For me and my three companions, a sojourn to Jewell Island is exactly the kind of adventure we were looking for. We’re staying overnight at a coveted campsite on the southernmost tip of the island. According to the guidebook from the Maine Island Trail Association (MITA), the nonprofit that manages the trail, the site is located on a secluded cobble beach with unbelievable views of the open ocean, and it’s easily accessible on a calm day. “It’s the last big island before Ireland,” Doug Welch, executive director of MITA, told me over the phone before we left.

As we paddle, my mind flashes back to earlier that morning. There we stood, huddled around the map of Casco Bay with Zack Anchors, owner of Portland Paddle and our sea kayaking guru, who had just outfitted us with a colorful fleet of seaworthy vessels and gear. We had arrived two hours ahead of time to organize and pack the boats, timing it just right to paddle out with the rising tide for a smooth departure. There was an air of nervous excitement in the group as Anchors counseled us on which route to take (begin at the East End public boat launch and paddle northeast, in between Peaks and Cow Island to Little Chebeague, then go directly east to Jewell Island), how to steer clear of lobster boats (give them plenty of space), and where to take a break. “Little Chebeague Island is a great halfway point to stop and stretch your legs,” he told us. You can also stay the night if you need to avoid rough or big swells—big being three feet or more.

However, it’s a perfectly clear August day, and the surface glitters as it softly ripples around us. I can feel the hot sun beating down on my shoulders and the sting of a blister forming where I’m gripping my paddle with salt-encrusted hands. I recall a tip that our instructor, Joe Guglielmetti, shared during our self-rescue clinic: unclench your fist so the power of each stroke originates from your core and not just your arms.

I pause to gulp down some water and notice for the third time the shiny black head of a seal emerging from the bay alongside my boat and wearing a curious expression on its whiskered face. I count the sea dog as our cohort in adventure and our watery guide—adorable and mysterious all at once. It slinks below the surface, and I take its disappearance as my cue to dig in and push on to Jewell.

Secured beneath the hatches in our kayaks are camping gear, food, and extra layers packed away in dry bags. There is also a soft cooler full of Rising Tide Brewing Company’s Maine Island Trail Ale (a portion of the beer’s proceeds benefit MITA). We packed it in ice, though the heat has surely melted it by now, and are hoping to enjoy at least mildly cold beverages on the island. Preparation is key, you know.

After 30 minutes of paddling determinedly, we exit the channel from Long Island to Jewell and catch our first glimpse of the island’s southern tip jutting out into the Atlantic. The campsite is within reach, tucked away in its protected cove just around the corner. This approach requires us to briefly abandon the safety of Casco Bay and paddle out into open ocean (a quarter of a nautical mile or so), then we will be on the lookout, portside, for the cove’s entrance, its cobble beach, and the elusive campsite.

For a moment or two, I feel my stomach lurch and my senses heighten as we paddle through the chop and hear the sharp cry of gulls overhead. Maybe it’s a combination of my boat rocking with the sea’s swell and the infinite blue water in front of me that makes me pause, but I realize that I’ve never been out in the open ocean in a vessel this size before. I know I’m safe and close to landing, yet the reality of this wild and wonderful moment in time hits me with an unexpected force. The journey to Jewell is as exhilarating as discovering the island itself.

We turn the corner and arrive at the mouth of the cove, where an underwater forest of translucent green seaweed waves us toward an empty campsite. Equal parts relief and amazement wash over us. It is as beautiful and wild as we had been told. We feel like a band of pirates who’ve uncovered buried treasure as our boats hit the sand with a thud, and we triumphantly step onto the shores of Jewell Island ready for a night under the stars.

To prevent our kayaks from being swept away by the tide overnight, we pull them in well past the high-water mark. Rockweed covers the shoreline, and it squeaks and squishes beneath our feet as we eagerly unpack the boats. After making camp, the four of us venture off into the island’s thick buffer of white spruce and rugosa rose bushes to gather downed and dead wood for a campfire. The trail system is extensive, and the island’s habitat transforms from rocky coastline to pristine woodland in a matter of minutes. Once we have a sufficient amount of firewood, we carry our haul back to the campsite and begin to cook a dinner of grilled caprese sandwiches by the light of an open fire.

Slowly, a full moon rises as the sun sinks below the horizon. We perch ourselves atop a craggy bluff facing southwest, sandwiches and beers in hand, to take in a truly glorious sunset over the bay. The next morning, a sunrise gently stirs us awake, and we linger on the shore sipping steaming cups of coffee before the final push-off.

It’s clear that part of Jewell’s magic is its liminality: just as it sits between Casco Bay and the North Atlantic, it also seems to exist between imagination and reality. The unspoiled landscape is wild and utopic—an ephemeral experience that’s there and gone as quickly as the changing tides. Words will never really do it justice; the only way to truly understand is to go there yourself.


Our beachfront campsite on the southern tip of Jewell Island was spacious, secluded, and scenic. There was enough room to comfortably pitch three tents, lay down a large blanket, and pull our kayaks above the high-tide line to prevent the ocean from carrying them away (don’t forget this!). It felt like our own private island.

However, that isn’t the case for every site. Most of the remaining sites are located on the west side, except for one on the northern end of the island. If you want to feel really secluded, go for the north or south site. Cocktail Cove (a popular spot between Jewell and Little Jewell, where boaters often drop anchor in the calm waters of its natural harbor) faces five of the campsites on the west side.

Footpaths wind through the island’s pine and spruce forests, over rocky ledges, and across sandy beaches, inviting explorers to experience more of Jewell’s mystique. At the southern end, the Towers Trail takes you to the ruins of WWI and WWII observation towers that offer a panoramic view of Casco Bay from way up high.


LENGTH OF TRIP: Overnight to a maximum two-night stay
DISTANCE: 16 miles round-trip
DIFFICULTY: Intermediate—must have some paddling and camping experience and be able to paddle for a few hours at a time
PERMITTING: No permit required
CAMPSITES: 12 primitive camp-sites—first-come, first-served
PETS: Pets allowed on leash; pack out all solid waste
BEST TIME TO GO: Midweek, from June through September
OTHER DETAILS: Good for small and larger groups. Pack in, pack out all waste and belongings. There are privies on the island, but it is recommended to bring your own toilet paper. Fires are allowed in designated fire rings only.


Preparedness is vital, and there’s no better way to get the information and resources you need than through the Maine Island Trail Association. Become a member and get a copy of MITA’s guidebook, which is essential for planning your trip. For $45 you’ll be granted access to the organization’s maps, trail guides, campsite information, and a mobile app.

Enroll in a self-rescue course to learn how to safely get yourself or another paddler back into a boat in case of capsizing. Portland Paddle offers three-hour-long clinics in Casco Bay with an experienced guide who’ll teach you how to implement the techniques while in the water and use the rescue gear. It put me at ease knowing that I had the skills to handle an emergency situation in the ocean.


You can rent gear from Portland Paddle, which is located on the East End Beach. The company will outfit you with all the gear you need but requires that you know how to perform a self-rescue if you’re renting for an overnight trip. Aside from the rental gear listed below, we were responsible for bringing all of our camping gear, clothing, food, and cookware.

• Sea kayak
• Paddle
• Spray skirts
• Life vest
• Medium dry bag
• Bilge pump

We brought extra dry bags and waterproof baggies for stashing small items that we wanted easily accessible (water, food, sunscreen, electronics, first-aid, and maps) while paddling. Attached to the bow of the boat was a compass for navigation.

As for backpacking, pack light and bring only the essentials. Yet, unlike back-packing, weight isn’t as important as volume. The more compact you can make things, the easier they’ll be to pack. Everything should be well sealed, or it will get damp, so it’s wise to use dry bags or plastic bags as a barrier. Stash your heaviest items (heavy gear and water) low and centered. Distribute everything else evenly around them, saving the lightest items for the bow and stern.

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