Portland Paddle offers scheduled guided trips to islands, or you can request specific dates that work for you. (Portland Phoenix/Shannon Bryan)
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Islands rule.

For those of us who don’t have the honor of existing on an island all the time, the prospect of paddling out to one of Maine’s craggy isles to camp out under the summer moon and fall asleep to the sound of salt water rushing over coastal rocks is pretty much definitely a dream come true. 

If you live on or otherwise have regular access to an island, I hope you camp on it all the time. The rest of us can still borrow one for a night or two. Maine has a bunch, and many of them welcome day visitors and overnight campers who can tuck their tents under the shade of tall pines or splay out in the grass in full view of the ocean. 

Kayakers’ encampment on the shore of Jewell Island. (Portland Phoenix/Shannon Bryan)

Locals with their own gear and know-how can plan their own island getaway. The best resource for plotting such an excursion is the Maine Island Trail Association, a Portland-based organization that administers a 375-mile recreational water trail along Maine’s coast, connecting more than 240 wild islands and mainland sites.

In addition to supporting some excellent island stewardship long into the future, a MITA membership includes a printed guidebook and an app (you can choose to get both or just the app) that highlight all the islands on the trail. The guidebook includes a host of useful island info like who owns the island, the best spot to land your boat, and whether you can camp there, plus info on pets, fires, and other features you’ll find – privies, tent platforms, trails, or sandy beaches perfect for swimming and sunning. 

If you’re not quite ready to set off on your own – because you lack gear and/or are new to sea kayaking – you’ll be in grand paddling hands on a guided overnight trip with Portland Paddle. (If it’s just the gear you need, you can rent a kayak from Portland Paddle and take it wherever you’d like to go.)

Portland Paddle offers guided trips to islands in Casco Bay and Muscongus Bay; there are scheduled trips all season or you can request specific dates that work for your group. Trips are led by a registered Maine guide who will stay apprised of changing tides and sea conditions, chart the course, and even take care of building a campfire and cooking dinner on the island. It’s pretty fantastic. 

Portland Paddle has all the necessary gear, too: A sea kayak, paddle, life jacket, and dry bags are included in the cost of a multi-day trip. 

Safety is of the utmost priority when on the water (another reason why paddling with a guide is a good idea when venturing farther afield), but you don’t need to be a highly seasoned sea kayaker to take part in these trips. A solid comfort and fitness level to be on the water paddling for hours helps, though. 

The view from a tent after waking up on Jewell Island during a two-day kayaking excursion. (Portland Phoenix/Shannon Bryan)

Jewell Island overnight

One of Portland Paddle’s multi-day trip options is Jewell Island in Casco Bay. Jewell is a popular summer spot for island campers and day-trippers on account of its open-ocean views, climbable fire towers, pretty island walking path, and hangout swim spot known as the “Punchbowl.”

The jaunt to Jewell is a two-day escapade that begins at Portland Paddle’s rental location near East End Beach in Portland. Here you’ll meet your guide, load up your boats, and go over the trip plan. You can bring your own kayak; otherwise, Portland Paddle has you covered with all the essentials.

Step one of your adventure is figuring out how to cram all the gear – sleeping bags and pillows and clothes and camp stoves and marshmallows and boxed wine – into your group’s kayaks. Magically, it all fits. (If it doesn’t, remember: you can use marshmallows as a pillow but you can’t eat a pillow with chocolate and graham crackers.)

After a safety talk and some paddling pointers, you’re off. The specific course will change depending on tides and wind, but Casco Bay is stunning in any direction. On your way to Jewell, you might stop for lunch on Vaill Island’s western side. You might spot nosy seals, harbor porpoises, osprey, terns, and jellyfish. You’ll almost certainly ooh and ahh at the surroundings: jagged shorelines, sunshine sparkling on the water, the way your boat rises and falls atop the waves.  

Landing on Jewell Island feels like a discovery, even if you’re quite aware humans have occupied this space for thousands of years. Once a campsite is claimed, you’ll spend some time setting up tents and rolling out sleeping bags. Then it’s time to explore the island. 

Jewell has a network of trails that connect one end to the other, sometimes leading to campsites or dumping you out onto a beach. The “Punchbowl” at the north end of the island is a popular spot for day visitors. You can climb the stairs and ladders up one of the fire control towers to enjoy the incredible views of the island and surrounding waters.

In addition to the towers, the remnants of other military structures – cement walls, iron bars, batteries, and barracks – are still evident, too.

Back at camp, enjoy a seaside dinner prepared by your guide and a sunset courtesy of the solar system. After the sky grows dark, you can hang out by the campfire, chatting and sipping wine, admiring the stars and the sea sounds, and already certain that this two-day island adventure is a highlight of your summer.

Freelance writer Shannon Bryan lives in South Portland and is the founder of fitmaine.com, where she writes about the coolest ways to be active and get outdoors in Maine.

No island kayaking adventure is complete without a campfire and s’mores. (Portland Phoenix/Shannon Bryan)

Portland Paddle has Jewell Island overnight trips scheduled Aug. 1-2, Aug. 16-17, Sept. 6-7, and Sept. 11-12. You can also request a time that works for your group. 

The cost is $245 per person (or $195 if you use your own sea kayak). It includes gear (sea kayak, personal flotation devices, paddle, dry bag), tents, and cooking equipment. Dinner, plus breakfast and lunch on the second day, are included. You bring your own sleeping bag and pad (you can also rent those from Portland Paddle) and lunch for day one.

FMI: portlandpaddle.net.