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Six Reasons We Love Sailing on Penobscot Bay

No list of “the best places to sail” is complete with mentioning Penobscot Bay.  The bay, about 40 miles long and 30 miles wide at its mouth, is the largest bay in midcoast Maine. For centuries Penobscot Bay has been coveted for its sheltered waters, proximity to the natural resources of lumber and granite, and position at the mouth of several rivers. Recreational sailors soon learned that its protected seas, steady breezes, and ample island-hopping opportunities make the bay an ideal place to sail. Add in its picturesque coastal towns and great wildlife viewing (seals, seals everywhere!), and we think you’ll agree that Penobscot Bay is a sailor’s paradise! 

Linda Cunningham Photo by Linda Cunningham

Quiet mornings and steady afternoon breezes: 

Mornings on the bay are the epitome of tranquility. The water is still, the atmosphere is quiet. There’s no traffic to be heard (or seen) except the sound of a passing lobster boat. Sitting on the deck of a boat in the morning you can hear fish splashing and osprey chirping. There’s no better place to clear your mind, center yourself and find gratitude for the day. By lunch though, the stillness gives way to the afternoon sea-breeze.  Count on 15 knots of wind to fill the sails for a rousing day of sailing.

Another peaceful morning on the bay with the Maine Windjammers. Photo: Bob Angell 

A multitude of islands: 

Penobscot Bay is home to over a hundred islands of various sizes. Some of the islands have small year-round communities (think 50 people and a one room school house!) but the majority are uninhabited. In the middle lie the large islands of Vinalhaven, North Haven, and Islesboro which are accessible by ferry and have larger populations.  Then, dotting the bay are the countless smaller islands with their rocky coastlines, pebbly beaches, hiking trails, and sheltered coves.  Winding your way through these archipelagos under sail and picking out a quiet cove to anchor is unparalleled in the sailing world. One of the most common things we hear from our new guests is how surprised they are at the number of islands and large selection of coves for anchoring.  We can sail all summer and never repeat our course! 

Photo by Dave Curtis

Flat seas: 

Thankfully, all these islands also shelter the bay from the ocean’s swell, knocking down the rolling waves before they can reach inner Penobscot Bay.  The sailing is smooth and seasickness is rarely a problem! 

Photo by Captain Noah Barnes

Unspoiled beauty: 

Maine is way up here and we like that! Maine’s remoteness keeps things beautiful. Exploring Penobscot Bay is so unique because the area hasn’t been bought up, built up and commercialized.  You won’t find any chain restaurants, water parks, or giant hotels looming over the islands. On the west side of Penobscot Bay sit the Camden Hills with their forested green peaks. To the north are the steep bluffs of Cape Rosier and to the east lie the many islands and island passages off of Deer Isle and Isle au Haut.  Look in any direction from the bay and you’ll see unspoiled Maine au natural. 

Photo by Quinton Donleavy

Small Coastal Towns:

There are several coastal towns along Penobscot Bay which are fun to explore. Two of the biggest towns are Camden and Rockland, home to the Maine Windjammer Association vessels. At the top of the bay is Castine, which has a rich maritime and Revolutionary War history.  In Castine one can visit the Maine Maritime Academy and the old British fort, Fort George, from Revolutionary times.  Another popular stop is Stonington on Deer Isle. Stonington is an authentic fishing town that’s also popular with artists and kayakers. The docks are alive with lobster boats loading and unloading crates of lobster and bait.  Belfast, North Haven village, and the town of Vinalhaven are also fun stops.  

Kenny Ames Photo by Kenny Ames


Famously, Rockport, Maine on Penobscot Bay was the home of Andre the Seal who was raised by Harry Goodridge in the ‘60’s, ‘70’s and ‘80’s.  Andre was a fixture in Rockport Harbor. For several winters, Mr. Goodridge brought Andre down to the aquarium in Boston, and in the spring, Harry would swim right back up to Rockport to his awaiting fans. Now, there’s a statue of him in Rockport Harbor. 

Though Andre was a special lad, he’s just one of the thousands of harbor seals and gray seals of Penobscot Bay. The many rocky ledges of the bay are prime real estate for seals dozing off as they sun themselves at low tide. At anchor you’ll often see a seal or two swim by or poke their head up to check you out.   

We consider ourselves lucky to live and work on Penobscot Bay and are thrilled to be able to share such a special place with our guests. 

Categories: Maine Islands, Maine Windjammers, Wildlife

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