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Maine: Penobscot Bay

Generations of sailors, artists, writers, and rusticators have all been drawn to the rugged beauty of the Maine coast, and one of the most popular areas is Penobscot Bay. You could spend a lifetime of summers here and never be at a loss for harbors to discover – and many are within a daysail or two of each other.

Fresh afternoon seabreeze and quiet evenings at anchor are some of the best parts of a Penobscot Bay charter.

The sailing season runs from July to September with foggy conditions a regular occurrence. But weather conditions can be highly localized, and fog off one island does not preclude clear sailing nearby. If you are lucky enough to sail here in September, you can count on clear bright warm days and cool nights with a hint of wood smoke in the air.

Penobscot Bay is the perfect place for any type of charter. Its three mainland harbors (Rockland, Rockport, and Camden) are home to a number of charter companies that offer crewed, bareboat, sail, and power of just about any size vessel, from runabout to superyacht.

Many of Maine’s boatyards and talented builders also offer select boats for charter. Some may be brokerage boats whose owners who are pleased to have them working while waiting for a sale. Quite often these are classic Maine-built boats that have been meticulously yard maintained.

Charters are usually contracted on a weekly basis, but some operators may consider less. One operator in Rockland will even rent by the day and has a sailing school with courses that include a basic bareboat chartering certification.

Rockland, Rockport, or Camden are all easily accessible by car, bus, or plane. Additionally, Rockland is home to the Maine State Ferry Service, which provides a regular connection to three important Bay islands - Vinalhaven, North Haven, and Matinicus. North of Camden, the Lincolnville ferry can also get you to Islesboro.

Shoreside Activities
Rockland, Rockport, and Camden offer restaurants, provisioning, water, fuel, and all sorts of marine services. The towns themselves are also important cultural and recreational centers of mid-coast Maine. Rockland is home to the Farnsworth Museum and its permanent collection of work by the Wyeths, headquarters the Island Institute, and is near to the Owl’s Head Transportation Museum. Rockport is home to Maine Media Workshops and several galleries.

Camden features a wide variety of music and art events, as well as the newly established Penobscot Bay Rendezvous for both sail and power, which takes place in August. There is also plenty of hiking and biking just a short walk from the harbor, at nearby Mount Battie State Park. And Lake Megunticook has canoeing, swimming, and rowing.

Regardless of where you choose to begin a charter, the real adventure begins on the bay. Here are three not-to-miss destinations:

Pulpit Harbor on North Haven Island

An easy sail from the Rockland breakwater, this is a well-protected harbor with a straightforward approach.

Carver’s Harbor, North Haven
This is the island’s main port on its western shore. For more than a century granite quarrying was the dominant industry here; some of the stone cut here went to build the Brooklyn Bridge and other notable structures. The last quarries were closed in 1939, but ghosts of the industry are everywhere you look. Many of the abandoned quarries are now swimming holes with granite tailings scattered about.

Today the ferry stops here and fishing dominates the harbor. As a result moorings are limited. But there are shops, a fully stocked market, and several restaurants to choose from.


About twelve nautical miles south of Carvers Harbor, Matinicus is Maine’s outermost island with a year-round population. Its remoteness is its charm.

Regardless of where you choose to explore, Penobscot Bay will not disappoint. You’ll surely enjoy your chance to get to know the Bay, its islands, and its people.

View a 7 day itinerary of Penobscot Bay

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