Sailing to Jewell Island

In an attempt to cram in as much adventure as possible before summer ends, I recently headed out on a sailing trip to Jewell Island free from the fun-destroying supervision of adults.  Luke Weiser provided the 27′ Catalina and Eliot Erickson, Dylan Greenlaw, Taylor Davis, and I were happy to take advantage of his generosity on the three-day trip.  After all, the best boat is one owned by someone else.

Jewell Island is one of the outermost islands in Casco Bay and is approximately 8 miles from Portland. At 221 acres, it has numerous trails and World War II bunkers and towers, and is one of the biggest and most popular islands on the Maine Island Trail.

All photos were shot on Kodak Portra 160 medium format film

Getting There

We started off from the Sail Maine dock in Portland and tacked through Diamond Pass into Hussey Sound. We expected some wind around Long Island, but were disappointed and were forced to motor to Jewell. Even with wind and swells, there are protected routes to Jewell for kayakers and boaters.

An old map of Jewell Island

Camping on Jewell

By far the best place to anchor on Jewell is Cocktail Cove. Located on the western edge of the island, between Jewell and Little Jewell Island, the cove provides plenty of protection from the wind and shelter from incoming swells. Along the western side of the island, there are also a number of campsites that make it easy to bring all of your gear ashore.

Our boat anchored in Cocktail Cove

Although there are numerous convenient sites, a walk across the island provides great views. We took the hard way and decided to lug our gear to the eastern side of the island. It took a number of trips, but we were rewarded with incredible sunrises over the open Atlantic.

The natural beauty of the island was outstanding

During our three days out on the island, we also were able to do some fishing and exploring. While hauling our gear we ran into a fisherman who gave us some advice about fishing the Punchbowl on the eastern side. Thanks to his advice, Eliot and I quickly doubled up on stripers using the ever-deadly white bucktail jig.

The view from the top of one of the WW II towers

Another incredible part of the island were the World War II towers that look over Casco Bay as well as the intricate bunkers that you can also explore. From the dilapidated houses to the musty bunkers the island is truly a gem.

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