Islands rule.

For those of us who don’t have the honor of living on an island all the time – or even some of the time – the prospect of even one night camped out on a rocky beach watching the moon rise over the water and dozing off to the sound of lapping waves is sort of a summer 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. Casco Bay has a bunch. And to make the island camping experience even more wonderful and neat, we can rally a few friends, pack up our kayaks, and paddle out to an overnight adventure on an island of our choice (except not ANY island – maybe choose one that allows overnight camping).

Into the great wide open during a weekend trip to Jewell Island with Portland Paddle. Shannon Bryan photo

To help in this endeavor, Portland Paddle leads guided overnights to islands in Casco Bay and Muscongus Bay. The are scheduled trips all season, or you can request specific dates that work for you.

Of course, you’re certainly welcome to kayak to an island and camp on it all on your own, but there are some splendid perks to a guided trip. First off, if your sea kayaking experience is limited, you’ll be in good hands with a Maine Guide who’ll stay apprised of sea conditions and tides and will chart the course and even take care of building a campfire and cooking dinner on the island. It’s pretty fantastic. Also, if you don’t own all the gear, Portland Paddle has it. A sea kayak, paddle, life jacket, and dry bags are included. Nice.

Staying safe 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 it’s also worth noting that don’t need to be a highly seasoned sea kayaker to take part in these trips. A level of comfort and fitness to be paddling on the water for hours is wise, though!

A few of our crew, including Portland Paddle guide Melanie in the background, as we packed up our boats and readied ourselves – and the flamingo – for adventure. Shannon Bryan photo

I’ve personally had my eye on the Jewell Island overnight for years. My friend Wendy has, too. So this summer we decided it was high time to make it happen. In early August we rallied some daring members of the Fit Maine Social Club and had ourselves a kayaking and camping adventure!

Our two-day escapade started at Portland Paddle’s location near East End Beach. Here we met up with our excellent guide Melanie and began the process of grabbing our kayaks and stuffing them full of gear. You can bring your own kayak if you have one, but it’s also nice to know that all the necessities are provided if you need them, including tents and other camping gear (BYO sleeping bag and pad – but if you don’t own those, you can rent them from Portland Paddle).

Paddle tips with guide Melanie before heading out. Shannon Bryan photo
Portland Paddle guide Melanie goes over the day’s course to Jewell Island. Shannon Bryan photo

We got some paddling tips (Feet to seat! Use your core!) and went over the day’s planned course – an island hop from Portland to Vaill for lunch, then on to Jewell. And once we had our boats jammed full of the necessities (pillow, camp stove, marshmallows, boxed wine) it was time to head down to the water and get ourselves launched.

Team work bringing all the loaded-up boats to the water. Shannon Bryan photo
Ready to go. Shannon Bryan photo
This is how Wendy and I feel about our long-awaited paddle to Jewell Island. Shannon Bryan photo

And then we were off.

Leaving Portland in our wake. Shannon Bryan photo
Paddle away. Shannon Bryan photo

We paddled at a not-so-fast pace for about an hour and a half, making sure to stay close together so we could communicate and to make sure our lively group was easier to spot by passing boaters. We sometimes paused to let boats go by or to check traffic before making a crossing from one pile of land to another. Melanie only had to yell at us to maintain our “blob formation” a couple of times (it’s easy to get distracted out there).

Around lunchtime we pulled up onto the sandy beach on Vaill Island’s western side (overlooking the beach on Long Island) to stretch our legs and put some food in our faces.

The beach on Vaill Island. Shannon Bryan photo
Lunch perch. Shannon Bryan photo
Not unhappy about the view. Shannon Bryan photo

Vaill Island is a splendid stopover – and we clearly weren’t the only people to think so. Boaters came ashore to soak in some sun and hang out for a bit. And we might’ve been just fine to stay there all day, but Jewell Island called. So back in the kayaks we went to keep on paddling.

Windier conditions on the water after lunch. Shannon Bryan photo
A bit of wave action in Casco Bay. Shannon Bryan photo
Jewell Island is in sight! And so is a flamingo! Shannon Bryan photo

The winds picked up a bit after lunch – and so the waves did, too. It was choppy going for a while, so it was nice to see Jewell Island grow closer. And in no time we were staking our claim on the south end of the island.

Landed. Jewell Island. Shannon Bryan photo

Our first goal: Set up camp. We opted to pop up our tents right on the rocky beach. There was a fire pit with drift-wood benches nearby, rocky cliffs, tall grasses and an ocean that stretched out forever. It was perfect.

This land is our land! At least for the evening. Shannon Bryan photo
A view of our campsite on the beach from one of the island trails. Shannon Bryan photo
Suzanne says hello from a rocky prominence by the campsite. Shannon Bryan photo

Once camp was settled and our sleeping bags rolled out, Melanie got to work on making dinner and gave us the go-ahead to explore for a bit. The island has a network of trails that connect one end to the other, sometimes leading to campsites or dumping you out onto a beach. Since this was my first-time-ever on Jewell, I was excited to see the popular Punchbowl at the north end of the island – a popular spot for day visitors.

Exploring the Punchbowl and every end of Jewell Island. Shannon Bryan photo
Rocky coast – so Maine. Shannon Bryan photo

A visit to Jewell wouldn’t be complete without climbing the stairs and ladders up one of the fire control towers to enjoy the incredible views of the island and surrounding waters.

One of the towers on Jewell Island. You can climb all up in there. Shannon Bryan photo
Entering the tower. Shannon Bryan photo
Several levels of stairs and ladders to get to the top level. There are windows along the way, allowing for enough light that you don’t need a headlamp. Shannon Bryan photo
Joan enjoys the view. Shannon Bryan photo
I went back to the tower the next morning and watched the sun rise up. Shannon Bryan photo

In addition to the towers, the remnants of other military structures is still evident, too. We poked around everything we came across – cement walls and iron bars and batteries and barracks.

An island lockup and a surprised face amid the rusting stuff. Shannon Bryan photos

We ran into a handful of other island overnighters. Being such a perfect summer evening, I’d half expected the island to be slammed with people. And I think most of the campsites were taken. But it didn’t feel crowded or busy where we were. In fact, it felt like we had a little slice of Jewell all to ourselves.

By the time we wandered back to camp, Melanie had a fire going and dinner ready: noddles and peanut sauce, along with hummus and peppers.

Dinner! Shannon Bryan photo

We scarfed that dinner down in no time, appreciating Melanie’s skills and the reality that we didn’t do a darn thing to help. It’s not that we didn’t want to help – we’d just gotten distracted by the island and trails and towers and military debris. Anyway, thanks Melanie.

Of course, it wouldn’t be camping without the traditional camp dessert.

Obligatory s’more photo. Shannon Bryan photo

Then we just hung out by the fire, chatting and sipping wine, admiring the stars and the sea sounds. And eventually we went to bed.

The next morning: more exploring. I wandered new trails, finding one that had buoys hanging from the trees, which led to another campsite.

Morning! Shannon Bryan photo
Buoy trail. Shannon Bryan photo

Heather, Melanie, and I also crept inside one of the batteries – HEADLAMPS FOR SURE – which was creepy as all get-out. There were for-real spiders, which were minding their own business but still, and a haunted-torture-chamber-zombie-hell-getway vibe that heightened with every step. Fun!

One of the batteries on Jewell Island. Inside is muy creepy. Definitely want a headlamp for that. Shannon Bryan photos
Exploring the battery/fending off demons. Shannon Bryan photo

After we’d had a breakfast of coffee, oatmeal, blueberries, and maple syrup, we began the sad process of packing up camp. It was too soon. One night here was not even remotely enough. On second thought, we’d decided, we should have booked a week-long stay. But there were jobs to return to and appointments to keep – and someone was likely to notice if Melanie didn’t return to Portland Paddle on time – so we rolled up our tents, re-crammed our things into every available nook and cranny in our kayaks, and got ready to leave.

But before our water shoes stepped off the island, we group photoed.

Group photo before we depart. Taken by Melanie!
Setting off from Jewell Island. Shannon Bryan photo

Unlike the rough waters of the day before, Sunday’s seas were glasslike and glorious.

Our paddle back was leisurely, interrupted a few times by habor seal and harbor porpoise spottings.

Once again we landed on Vaill Island for lunch. Suzanna and Jen took a dip in the waters, we narrowly avoided sitting in poison ivy, and it was right about here that we started talking about turning back toward Jewell and never going home.

Return trip to Vaill Island. Shannon Bryan photo

Portland in view. Home again. Shannon Bryan photo

But alas, we continued on until Portland came into view and we knew that our two-day dream of a get-away was coming to a close. Back on land, we unpacked our boats and said our goodbyes, thanking Melanie for being a stand-out guide and island compatriot.

We trodded back to our cars with dry bags slung over our shoulders, feeling like we’d been away for days or weeks, not just the mere 30-or-so hours it had been. And we agreed our kayaking and camping adventure had been absolutely perfect. And that we were going to do it again as soon as possible.

Island glee. Shannon Bryan photos

Jewell Island overnight with Portland Paddle

There are a couple of scheduled trips to Jewell on the calendar, and you can also request trip dates that work for you/your group.
Cost is $235 per person (or $185 if you use your own sea kayak). Cost includes gear (sea kayak, pfd, paddle, dry bag) as well as tents and cooking equipment. Dinner, breakfast, and lunch on day two are also included. You bring your own sleeping bag and pad (you can also rent those from Portland Paddle) and lunch for day one.

And most importantly: you’ll have one of Portland Paddle’s guides leading the way (they tend to be a lot of fun to hang out with, too).

For more info on the Jewell trip:

Also check out all of Portland Paddle’s multi-day trips, including the Casco Bay Traverse and Muscongus Bay Expedition.

Note: this post was originally published August 28, 2019. Portland Paddle is open for tours and guided trips and CDC guidelines regarding masks and social distancing are in place.